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David E. Cane Publications

1. E. J. Corey and David E. Cane, "The Synthesis of Olefins from β-Hydroxyphosphonamides. Stereochemistry and Extension to the Formation of Conjugated Dienes," J. Org. Chem., 34, 3053 (1969).

2. E. J. Corey and David E. Cane, "The Metalation-Alkylation of Ynamines," J. Org.Chem., 35, 3405 (1970).

3. E. J. Corey and David E. Cane, "A New Method for the Controlled Hydroxymethylation of Ketones," J. Org. Chem., 36, 3070 (1971).

4. E. J. Corey, David E. Cane, and Lawrence Libit, "The Synthesis of Racemic α-trans- and β-trans-Bergamotene," J. Am. Chem. Soc., 93, 7013, (1971).

5. D. Arigoni, David E. Cane, Beat Mueller and Christopher Tamm, "The Mode of Incorporation of Farnesyl Pyrophosphate into Verrucarol," Helv. Chim. Acta, 56, 2946 (1973).

6. David E. Cane and Ronald H. Levin, "Application of Carbon-13 Magnetic Resonance to Isoprenoid Biosynthesis. I. Ovalicin," J. Am. Chem. Soc., 97, 1982 (1975).

7. David E. Cane and Ronald H. Levin, "Application of Carbon-13 Magnetic Resonance to Isoprenoid Biosynthesis. II. Ovalicin and the Use of Double-Labeled Mevalonate," J. Am. Chem. Soc., 98, 1183 (1976).

8. David E. Cane and Robert B. Nachbar, "Biosynthesis of Fomannosin from [1,2-13C]-Acetate," Tetrahedron Lett. 2097-2100 (1976).

9. David E. Cane and G. G. S. King, "The Biosynthesis of Ovalicin: Isolation of β-trans-Bergamotene," Tetrahedron Lett.., 4737 (1976).

10. David E. Cane and Stephen L. Buchwald, "Application of Deuterium Magnetic Resonance to Biosynthetic Studies I; Biosynthesis of Ovalicin," J. Am. Chem. Soc., 99, 6132 (1977).

11. David E. Cane and Radha Iyengar, "The Absolute Configuration of Cyclonerodiol," Tetrahedron Lett., 3511 (1977).

12. David E. Cane, Robert B. Nachbar, Jon Clardy, and Janet Finer, "The Absolute Configuration of Fomannosin," Tetrahedron Lett., 4277 (1977).

13. David E. Cane and Ming-Shi Shiao, "Biosynthesis of Cyclonerodiol," J. Am. Chem. Soc., 100, 3203 (1978).

14. David E. Cane and Pushpalatha N. Murthy, "Application of Deuterium Magnetic Resonance to Biosynthetic Studies II. Rosenonolactone Biosynthesis and the Stereochemistry of a Biological SN2' Reaction," J. Am. Chem. Soc., 99, 8327 (1977).

15. David E. Cane and Robert B. Nachbar, "Stereochemical Studies of Isoprenoid Biosynthesis. Biosynthesis of Fomannosin from [1,2-13C]-Acetate," J. Am. Chem. Soc., 100, 3208 (1978).

16. David E. Cane and R. Iyengar, "Conversion of Farnesyl and Nerolidyl Pyrophosphate to Cyclonerodiol by a Cell-Free System from Gibberella Fujikuroi," J. Am. Chem. Soc.,100, 3256 (1978).

17. David E. Cane, Radha Iyengar, and Ming-Shi Shiao, "Cyclonerodiol Biosynthesis and the Stereochemistry of the Conversion of Farnesyl to Nerolidyl Pyrophosphate," J. Am. Chem. Soc., 100, 7122 (1978)

18. C. Richard Hutchinson, Amos H. Heckendorf, J. L. Straughn, P. E. Dadonna and David E. Cane, "The Biosynthesis of Camptothecin. III. Definition of Strictosamide as the Penultimate Biosynthetic Precursor Assisted by 13C and 2H NMR Spectroscopy," J. Am. Chem. Soc., 101, 3358 (1979). 19. David E. Cane, Thomas Rossi, and J. Paul Pachlatko, "The Biosynthesis of Pentalenolactone," Tetrahedron Lett., 3639-3642 (1979).

20. David E. Cane and Radha Iyengar, "Carbon-Carbon Bond Cleavage During Lithium Aluminum Hydride Reduction of a Terminal Propargyl Alcohol," Tetrahedron Lett., 2871 (1979).

21. David E. Cane and Thomas Rossi, "The Isolation and Structural Elucidation of Pentalenolactone E," Tetrahedron Lett., 2973 (1979).

22. David E. Cane and Radha Iyengar, "The Enzymatic Conversion of Farnesyl to Nerolidyl Pyrophosphate: Role of the Pyrophosphate Moiety," J. Am. Chem. Soc., 101, 3385-3388[1, 2] (1979).

23. David E. Cane and Robert B. Nachbar, "Biosynthesis of Fomannosin. 2H NMR Evidence Against Postulated Hydride Shifts," Tetrahedron Lett., 21, 432 (l980).

24. David E. Cane, "The Stereochemistry of Allylic Pyrophosphate Metabolism," Tetrahedron Report, Tetrahedron, 36, 1109 (1980).

25. David E. Cane, Radha Iyengar and Ming-Shi Shiao, "Cyclonerodiol Biosynthesis and the Enzymatic Conversion of Farnesyl to Nerolidyl Pyrophosphate," J. Am. Chem. Soc., 103, 914 (1981).

26. David E. Cane, Thomas Rossi, Ann Marie Tillman, and J. Paul Pachlatko, "Stereochemical Studies of 13 2 Isoprenoid Biosynthesis. Biosynthesis of Pentalenolactone from [UL- C6]-Glucose and [6- H2]-Glucose," J. Am. Chem. Soc., 103, 1838 (1981).

27. David E. Cane, "The Biosynthesis of Sesquiterpenes," in "Biosynthesis of Isoprenoid Compounds," Vol 1, J. W. Porter, S. L. Spurgeon, ed., J. W. Wiley & Sons, New York, 1981, pp 283-374

28. David E. Cane, Heinz Hasler, Joan Materna, Nera Cagnoli-Bellavita, Paolo Ceccherelli, Gian Federico Madruzza, and Judith Polonsky, "2H NMR Determination of the Stereochemistry of an Allylic Displacement Reaction in the Biosynthesis of Virescenol B," J. Chem. Soc. Chem. Commun., 280 (1981).

29. David E. Cane, Stephen Swanson, and Pushpalatha P.N. Murthy, "Trichodiene Biosynthesis and the Enzymatic Cyclization of Farnesyl Pyrophosphate," J. Am. Chem. Soc., 103, 2136 (1981).

30. C. Richard Hutchinson, Itsuo Kurobane, David E. Cane, Heinz Hasler, and A. G. McInnes, "Biosynthesis of 2 Macrolide Antibiotics IV. Stereochemistry of Hydrogen Labeling of Brefeldin A by [2- H3]-Acetate," J. Am. Chem. Soc., 103, 2477 (1981).

31. David E. Cane, Heinz Hasler, and Tzyy-Chyau Liang, "Macrolide Biosynthesis. Origin of the Oxygen Atoms in the Erythromycins," J. Am. Chem. Soc., 103, 5960 (1981).

32. David E. Cane, Tzyy-Chyau Liang, and Heinz Hasler, "Polyether Biosynthesis. Origin of the Oxygen Atoms of Monensin A," J. Am. Chem. Soc., 103, 5962 (1981).

13 33. Steven J. Gould and David E. Cane, "The Biosynthesis of Streptonigrin from [UL- C6]-D-Glucose. Origin of the Quinoline Quinone," J. Am. Chem. Soc., 104, 343 (1982).

34. David E. Cane, Akio Saito, Rodney Croteau,John Shaskus, and Mark Felton, "The Enzymatic Cyclization of Geranyl Pyrophosphate to Bornyl Pyrophosphate. Role of the Pyrophosphate Moiety," J.Am. Chem. Soc., 104, 5831 (1982).

35. David E. Cane, Tzyy-Chyau Liang, and Heinz Hasler, "Polyether Biosynthesis II. Origin of the Oxygen Atoms of Monensin A," J. Am. Chem. Soc., 104, 7274 (1982).

2 36. Ann Marie Tillman and David E. Cane, "Pentalenolactone F, A New Metabolite Isolated from Streptomyces. Isolation and Structure Elucidation," J. Antibiot., 36, 170-172 (1983).

37. David E. Cane, Walter D. Celmer, and John W. Westley, "A Unified Stereochemical Model of Polyether Structure and Biogenesis," J. Am. Chem. Soc., 105, 3594-3600 (1983).

38. David E. Cane and Ann Marie Tillman, "Pentalenene Biosynthesis and the Enzymatic Cyclization of Farnesyl Pyrophosphate," J. Am. Chem. Soc., 105, 122-124 (1983).

39. David E. Cane, "-Level Studies of the Biosynthesis of Natural Products," in "Enzyme Chemistry, Impact and Applications" C. J. Suckling, ed., Chapman and Hall, London, 1984, pp. 196-231.

40. David E. Cane, Heinz Hasler, Paul B. Taylor, and Tzyy-Chyau Liang, "Macrolide Biosynthesis. II. Origin of the Carbon Skeleton and Oxygen Atoms of the Erythromycins," Tetrahedron, 39, 3449 (1983).

41. David E. Cane, Tzyy-Chyau Liang, Louis Kaplan, Mary K. Nallin, Marvin D. Schulman, Otto D. Hensens, Alan W. Douglas, and George Albers-Schonberg, "The Biosynthetic Origin of the Carbon Skeleton and Oxygen Atoms of the Avermectins", J. Am. Chem. Soc., 105, 4110 (1983).

42. David E. Cane, "Cell-Free Studies of Monoterpene and Sesquiterpene Biosynthesis," Biochem. Soc. Trans., 11, 510-516 (1983).

43. R. Croteau, John Shaskus, David E. Cane, Akio Saito, and Conway Chang, "The Enzymatic Cyclization of [1- 18O]Geranyl Pyrophosphate to l-endo-Fenchol," J. Am. Chem. Soc., 106, 1142 (1984).

44. David E. Cane and Chi-Ching Yang, "The Biosynthetic Origin of the Carbon Skeleton and Oxygen Atoms of Nargenicin A1," J. Am. Chem. Soc., 106, 784 (1984).

45. Rodney Croteau and David E. Cane, "Monoterpene and Sesquiterpene Cyclases," in "Methods in Enzymology. Steroids and Isoprenoids," Vol. 110, J. H. Law and H. C. Rilling, eds., Academic Press, New York, 1985; pp 383-405.

46. David E. Cane, Yvonne G. Whittle, and Tzyy-Chyau Liang, "The Biosynthesis of Quadrone and Terrecyclic Acid," Tetrahedron Lett., 25, 1119 (1984).

47. David E. Cane and Pulikkottil J. Thomas, "The Synthesis of (dl)-Pentalenolactones E and F," J. Am. Chem. Soc., 106, 5295 (1984).

48. David E. Cane, Christopher Abell, and Ann Marie Tillman, "Pentalenene Biosynthesis and the Enzymatic Cyclization of Farnesyl Pyrophosphate. Proof that the Cyclization is Catalyzed by a Single Enzyme," Bioorganic Chemistry, 12, 312 (1984).

49. David E. Cane and Chi-Ching Yang, "Nargenicin Biosynthesis. Late Stage Oxidations and Absolute Configuration," J. Antibiot., 38, 423-426 (1985).

50. David E. Cane, Hyun-Joon Ha, Christopher Pargellis, Felix Waldmeier, Stephen Swanson, and Pushpalatha P. N. Murthy, "Trichodiene Biosynthesis and the Stereochemistry of the Enzymatic Cyclization of Farnesyl Pyrophosphate," Bioorganic Chemistry, 13, 246 (1985).

51. David E. Cane, "Isoprenoid Biosynthesis. Stereochemistry of the Cyclization of Allylic Pyrophosphates," Acc. Chem. Res., 18, 220 (1985).

52. Rodney B. Croteau, John J. Shaskus, Britta Renstrom, N. Mark Felton, David E. Cane, Akio Saito, and Conway Chang, "Mechanism of the Pyrophosphate Migration in the Enzymatic Cyclization of Geranyl and Linalyl Pyrophosphate to (+)- and (-)-Bornyl Pyrophosphate," Biochemistry, 24, 7077 (1985).

3 53. David E. Cane, "Stereochemical Studies of Natural Products Biosynthesis," Ann. N. Y. Acad. Sci., 471, 130-137 (1986).

54. David E. Cane, Tzyy-Chyau Liang, Paul B. Taylor, Conway Chang, and Chi-Ching Yang, "Macrolide Biosynthesis. 3. Stereochemistry of the Chain-Elongation Steps of Erythromycin Biosynthesis," J. Am. Chem. Soc., 108, 4957 (1986).

55. David E. Cane and Hyun-Joon Ha, "Trichodiene Biosynthesis and the Enzymatic Cyclization of Nerolidyl Pyrophosphate," J. Am. Chem. Soc., 108, 3097 (1986).

56. David E. Cane, Yvonne G. Whittle, and Tzyy-Chyau Liang, "Sesquiterpene Biosynthesis. The Biosynthesis of Quadrone and Terrecyclic Acid," Bioorganic Chemistry, 14, 417 (1986)

57. Rodney Croteau, D. Michael Satterwhite, David E. Cane, and Conway C. Chang, "Biosynthesis of Monoterpenes: Enantioselectivity in the Enzymatic Cyclization of (+)- and (-)-Linalyl Pyrophosphate to (+)- and (-)-Bornyl Pyrophosphate," J. Biol. Chem., 261, 13438 (1986).

58. David E. Cane and Christopher Pargellis, "Sesquiterpene Biosynthesis. Partial Purification and Characterization of Pentalenene Synthetase," Arch. Biochem. Biophys., 254, 421 (1987).

59. David E. Cane and Chi-Ching Yang, "Macrolide Biosynthesis. 4. Intact Incorporation of a Chain Elongation Intermediate Into Erythromycin," J. Am. Chem. Soc., 109, 1255 (1987).

60. Rodney B. Croteau, Carl J. Wheeler, David E. Cane, Roxanne Ebert, and Hyun-Joon Ha, "Isotopically Sensitive Branching in the Formation of Cyclic Monoterpenes: Proof that (-)-(α)-Pinene and (-)-(β)-Pinene are Synthesized by Sage Cyclase II by Deprotonation of a Common Intermediate," Biochemistry, 26, 5383 (1987).

61. David E. Cane, Bernard J. Rawlings, and Chi-Ching Yang, "Isolation of (-)-γ-Cadinene and Aristolochene from Aspergillus Terreus," J. Antibiot., 40, 1331-1334 (1987).

62. David E. Cane and Brian R. Hubbard, "Polyether Biosynthesis. 3. Origin of the Carbon Skeleton and Oxygen Atoms of Lenoremycin," J. Am. Chem. Soc., 109, 6533 (1987).

63. David E. Cane and Douglas B. McIlwaine, " The Biosynthesis of Ovalicin from β-trans-Bergamotene," Tetrahedron Lett., 28, 6545 (1987).

64. Paul G. Williard, Jae Kyung Sohng, and David E. Cane, "The X-Ray Crystal Structure of Pentalenolactone F Methyl Ester, (Epi-Pentalenolactone F)," J. Antibiot. 41, 130 (1988).

65. Rodney Croteau, D. Michael Satterwhite, David E. Cane, and Conway C. Chang, "Enantioselectivity in the Enzymatic Cyclization of (+)- and (-)-Linalyl Pyrophosphate to (+)- and (-)-Pinene and (+)- and (-)-Camphene, J. Biol. Chem., 263, 10063-10071 (1988).

66. Michael H. Block and David E. Cane, "Synthesis of Proposed Chain Elongation Intermediates of the Monensin Biosynthetic Pathway," J. Org. Chem., 53, 4923 (1988).

67. David E. Cane and Walter R. Ott, "Macrolide Biosynthesis. 5. Intact Incorporation of a Chain Elongation Intermediate Into Nargenicin," J. Am. Chem. Soc., 110, 4840 (1988).

68. David E. Cane, Christopher Abell, Rene Lattman, Charles T. Kane, Brian R. Hubbard, and Paul H. M. Harrison, "Pentalenene Biosynthesis and the Enzymatic Cyclization of Farnesyl Pyrophosphate. Anti Stereochemistry in a Biological SE' Reaction," J. Am. Chem. Soc.,110, 4081 (1988).

69. David E. Cane and Hyun-Joon Ha, "Trichodiene Biosynthesis and the Role of Nerolidyl Pyrophosphate in the Enzymatic Cyclization of Farnesyl Pyrophosphate," J. Am. Chem. Soc., 110, 6865 (1988).

4 70. Paul H. M. Harrison, John S. Oliver, and David E. Cane, "Pentalenene Biosynthesis and the Enzymatic Cyclization of Farnesyl Pyrophosphate. Inversion at C-1 During 11-Membered Ring Formation" J. Am. Chem. Soc., 110, 5922 (1988).

71. David E. Cane, Chi-Ching Yang, and Walter R. Ott, "Biosynthesis of Macrolide Antibiotics," Proceedings of the Seventh International Symposium on Biology of Actinomycetes," Japan Antibiotics Research Association, 395 (1988).

72. David E. Cane, "Stereochemical Studies of Natural Products Biosynthesis," Pure Appl. Chem., 61, 493 (1989).

73. David E. Cane and Jae-Kyung Sohng, "Inhibition of Glyceraldehyde-3-Phosphate Dehydrogenase by Pentalenolactone. Kinetic and Mechanistic Studies," Arch. Biochem. Biophys. 270, 50-61 (1989).

74. David E. Cane, Douglas B. McIlwaine, and Paul H. M. Harrison, "Bergamotene Biosynthesis and the Enzymatic Cyclization of Farnesyl Pyrophosphate," J. Am. Chem. Soc. 111, 1152-1153 (1989)

75. David E. Cane, "The Enzymology of Natural Products Biosynthesis," in "Enzyme Chemistry, Impact and Applications," 2d edn, C. J. Suckling, ed., Chapman and Hall, London, 1990, pp. 265-305.

76. Doreen M. Ashworth, Duncan S. Holmes, John A. Robinson, Hideaki Oikawa and David E. Cane, "Selection of a Specifically Blocked Mutant of Streptomyces cinnamonensis. Isolation and Synthesis of 26- Deshydroxymonensin A," J. Antibiot. 42, 1088 (1989).

77. Ian M. Whitehead, P. C. Prabhakaran, David F. Ewing, David E. Cane, and David R. Threllfall, "Studies on the Biosynthesis of the Eremophilene Phytoalexins Capsidiol and Debneyol. Chemical Synthesis and Spectroscopic Study of (+)-5-epi- Aristolochene and (+)-1-Deoxycapsidiol from Capsidiol," Phytochemistry, 29, 479 (1990).

78. David E. Cane, P. C. Prabhakaran, E. J. Salaski, Paul H. M. Harrison, Hiroshi Noguchi, and Bernard J. Rawlings, "Aristolochene Biosynthesis and Enzymatic Cyclization of Farnesyl Pyrophosphate," J. Am. Chem. Soc., 111, 8914-8916 (1989).

79. David E. Cane, John S. Oliver, Paul H. M. Harrison, Christopher Abell, Brian R. Hubbard, Charles T. Kane, and Rene Lattman, "The Biosynthesis of Pentalenene and Pentalenolactone," J. Am. Chem. Soc. 112, 4513-4524 (1990).

80. David E. Cane, Douglas B. McIlwaine, and John S. Oliver, "The Absolute Configuration of (-)-β-trans- Bergamotene," J. Am. Chem. Soc, 112, 1285-1286 (1990).

81. David E. Cane, John L. Pawlak, R. Marthinus Horak, and T. M. Hohn, ". Studies of the Cryptic Allylic Pyrophosphate Activity Using the Anomalous Substrate 6,7-Dihydrofarnesyl Pyrophosphate," Biochemistry, 29, 5476 (1990).

82. David E. Cane, E. J. Salaski, and P. C. Prabhakaran, "Preparation of (-)-Aristolochene from (+)-Valencene: Absolute Configuration of (+)-Aristolochene from Aspergillus terreus," Tetrahedron Lett. , 31, 1943 (1990).

83. David E. Cane, P. C. Prabhakaran, John S. Oliver, and Douglas B. McIlwaine, "Aristolochene Biosynthesis. Stereochemistry of the Deprotonation Steps in the Enzymatic Cyclization of Farnesyl Pyrophosphate," J. Am. Chem. Soc., 112, 3209-3210(1990).

84. David E. Cane, "The Enzymatic Formation of Sesquiterpenes," Chem. Rev. 90, 1089 (1990).

85. David E. Cane, Douglas B. McIlwaine, Keith O. Pascoe, "The Synthesis of (3R)-Nerolidol," Tetrahedron Lett., 31, 7553 (1990).

86. David E. Cane, Christopher Abell, Paul H. M. Harrison, Brian R. Hubbard, Charles T. Kane, Rene Lattman, John S. Oliver, and Steven W. Weiner, "Terpenoid Biosynthesis and the Stereochemistry of Enzyme-Catalyzed Allylic Addition – Elimination Reactions," Phil. Trans. Roy. Soc. B., 332, 123 (1991).

5 87. David E. Cane, Editor,Tetrahedron Symposium-in-Print, "Frontiers in Natural Products Biosynthesis. Enzymological and Molecular Genetic Advances." Tetrahedron, 47 (31), 5919-6078 (1991).

88. David E. Cane, P. C. Prabhakaran, Weitian Tan, and Walter R. Ott, "Macrolide Biosynthesis. 6. Mechanism of Polyketide Chain Elongation," Tetrahedron Lett., 32, 5457 (1991).

89. David E. Cane, Jae Kyung Sohng, and Paul G. Williard, "Isolation and Structure Determination of Pentalenolactones A, B, D, and F," J. Org. Chem., 57, 844-851 (1992).

90. David E. Cane, "Isoprenoid Antibiotics," in "Genetics and Biochemistry of Antibiotic Production," Vining, L. C. and Stuttard, C., eds., Butterworth-Heinemann, Boston, 1995; pp 633-655.

91. David E. Cane, Guohan Yang, Robert M. Coates, Hyung-Jung Pyun, and Thomas M. Hohn, "Trichodiene Synthase. Synergistic Inhibition by Inorganic Pyrophosphate and Aza-Analogs of the Bisabolyl Cation," J. Org. Chem., 57, 3454-3462 (1992).

92. David E. Cane, "Terpenoid Cyclases - Design and Function of Electrophilic Catalysts," Ciba Foundation Symposium No. 171, Secondary Metabolites: Their Function and Evolution, John Wiley & Sons, Chichester, 1992; pp 163-183.

93. David E. Cane, Zhen Wu, and James E. Van Epp, "Thiotropocin Biosynthesis. Shikimate Origin of a Sulfur- Containing Tropolone Derivative," J. Am. Chem. Soc. 114, 8479 (1992).

94. Ralph H. Lambalot and David E. Cane, "Isolation and Characterization of 10-Deoxymethynolide Produced by Streptomyces venezuelae," J. Antibiotics, 45, 1981-1982 (1992).

95. David E. Cane, Ralph H. Lambalot, P. C. Prabhakaran, and Walter R. Ott, "Macrolide Biosynthesis 7. Incorporation of Polyketide Chain Elongation Intermediates into Methymycin," J. Am. Chem. Soc. 115, 522-526 (1993).

96. David E. Cane, Weitian Tan, and Walter R. Ott, "Nargenicin Biosynthesis. Incorporation of Polyketide Chain Elongation Intermediates and Support for a Proposed Intramolecular Diels-Alder Cyclization," J. Am. Chem. Soc. 115, 527-535 (1993).

97. Duilio Arigoni,David E. Cane, Jae Hoon Shim, Rodney Croteau and Kurt Wagschal, "Monoterpene Cyclization Mechanisms and the Use of Natural Abundance Deuterium N. M. R. - Short Cut or Primrose Path?" Phytochemistry, 32, 623-631 (1993).

98. David E. Cane, Zhen Wu, John S. Oliver, and Thomas M. Hohn, "Overproduction of Soluble Trichodiene Synthase from Fusarium sporotrichioides in Escherichia coli," Arch. Biochem. Biophys., 300, 416-422 (1993).

99. David E. Cane, "Commentaries on Selected Papers of Professor Sir John Warcup Cornforth," in Selected Papers of J. W. Cornforth, B. T. Golding, ed., Pergamon Press, Oxford, 1992, pp 143-144, 202-203, 355.

100. David E. Cane, Manish Tandon, and P. C. Prabhakaran, "Epi-Cubenol Synthase and the Enzymatic Cyclization of Farnesyl Diphosphate," J. Am. Chem. Soc. 115, 8103-8106 (1993).

101. David E. Cane, Zhen Wu, Robert H. Proctor, and Thomas M. Hohn, "Overexpression in Escherichia coli of Soluble from Penicillium roqueforti," Arch. Biochem. Biophys. 304, 415-419 (1993).

102. Rodney Croteau, William R. Alonso, Alfred E. Koepp, Jae Hoon Shim, and David E. Cane, "Irreversible Inactivation of Monoterpene Cyclases by a Mechanism-Based Inhibitor," Arch. Biochem. Biophys. 307, 397- 404 (1993).

103. David E. Cane and Steven W. Weiner, "Cyclization of Farnesyl Diphosphate to Pentalenene. Orthogonal Stereochemistry in an Enzyme-Catalyzed SEʹ Reaction," Can. J. Chem. 72, 118-127 (1994).

6 104. David E. Cane, Jae-Kyung Sohng, Carol R. Lamberson, Suzanne M. Rudnicki, Zhen Wu, Matthew D. Lloyd, John S. Oliver, and Brian R. Hubbard, ". Purification, Molecular Cloning, Sequencing and High-Level Expression in Escherichia coli of a Terpenoid Cyclase from Streptomyces UC5319," Biochemistry, 33, 5846-5857 (1994).

105. David E. Cane, "Control and Choice in Polyketide Biosynthesis: Molecular Recognition or Genetic Programming?" Science, 263, 338-340 (1994).

106. David E. Cane and Jae-Kyung Sohng, "Inhibition of Glyceraldehyde-3-phosphate Dehydrogenase by Pentalenolactone. 2. Identification of the Site of Alkylation by Tetrahydropentalenolactone," Biochemistry, 33, 6524-6530 (1994).

107. David E. Cane and Manish Tandon, "The Total Synthesis of (±)-Epicubenol," Tetrahedron Lett. 35, 5351-5354 (1994).

108. David E. Cane and Manish Tandon, "The Biosynthesis of (+)-Epicubenol," Tetrahedron Lett. 35, 5355-5358 (1994).

109. David E. Cane and Guohan Yang, "Trichodiene Synthase. Stereochemical Studies of the Cryptic Allylic Diphosphate Isomerase Activity Using an Anomalous Substrate," J. Org. Chem. 59, 5794-5798 (1994).

110. Camilla M. Kao, Guanglin Luo, Leonard Katz, David E. Cane, and Chaitan Khosla, "Engineered Biosynthesis of a Triketide Lactone from an Incomplete Modular ," J. Am. Chem. Soc. 116, 11612- 11613 (1994).

111. David E. Cane, Guohan Yang, Qun Xue, and Jae Hoon Shim, "Trichodiene Synthase. Substrate Specificity and Inhibition," Biochemistry, 34, 2471-2479(1995).

112. David E. Cane, Jae Hoon Shim, Xun Que, Brian C. Fitzsimons, and Thomas M. Hohn, "Trichodiene Synthase. Identification of Residues by Site-Directed Mutagenesis," Biochemistry, 34, 2480-2488 (1995).

113. David E. Cane and Clifford Bryant, "Aristolochene Synthase. Mechanism-Based Inhibition of a Terpenoid Cyclase," J. Am. Chem. Soc. 116, 12063-12064 (1994).

114. Ralph H. Lambalot, David E. Cane, Jose J. Aparicio, and Leonard Katz, "Overexpression and Characterization of the Erythromycin C-12 Hydroxylase, EryK," Biochemistry, 34, 1858-1866 (1995).

115. David E. Cane, Guanglin Luo, Chaitan Khosla, Camilla M. Kao, and Leonard Katz, Erythromycin Biosynthesis. Highly Efficient Incorporation of Polyketide Chain Elongation Intermediates into 6- Deoxyerythronolide B in an Engineered Streptomyces Host, " J. Antibiotics 48, 647-651 (1995).

116. David E. Cane and Manish Tandon, "Epicubenol Synthase and the Stereochemistry of the Enzymatic Cyclization of Farnesyl and Nerolidyl Diphosphate," J. Am. Chem. Soc. 117, 5602-5603 (1995).

117. David E. Cane and Guanglin Luo, "Biosynthesis of Polyketide Antibiotics. Incorporation of a Pentaketide Chain Elongation Intermediate into Nargenicin," J. Am. Chem. Soc. 117, 6633-6634 (1995).

118. Camilla M. Kao, Guanglin Luo, Leonard Katz, David E. Cane, and Chaitan Khosla, "Manipulation of Macrolide Ring Size by Directed Mutagenesis of a Modular Polyketide Synthase," J. Am. Chem. Soc. , 117, 9105-9106 (1995).

119. Rembert Pieper, Guanglin Luo, David E. Cane, and C. Khosla, "Cell-Free Biosynthesis of the Erythromycin Aglycone and a Triketide Lactone by a Modular Polyketide Synthase," Nature, 378, 263-266 (1995).

120. Charles A. Lesburg, Matthew D. Lloyd, David E. Cane and David W. Christianson, "Crystallization and preliminary X-ray diffraction studies on recombinant pentalenene synthase," Protein Science, 4, 2436-2438 (1995).

7 121. Rembert Pieper, Guanglin Luo, David E. Cane, and Chaitan Khosla, "Remarkably Broad Substrate Specificity of a Modular Polyketide Synthase in a Cell-Free System," J. Am. Chem. Soc. , 117, 11373-11374 (1995).

122. David E. Cane and Qun Xue, "Trichodiene Synthase. Enzymatic Formation of Multiple Sesquiterpenes by Alteration of the Cyclase Active Site," J. Am. Chem. Soc. , 118, 1563-1564 (1996).

123. Rembert Pieper, Susanne Ebert-Khosla, David Cane, and Chaitan Khosla, "Erythromycin Biosynthesis:Kinetic Studies On A Fully Active Modular Polyketide Synthase Using Natural and Unnatural Substrates," Biochemistry, 35, 2054-2060 (1996).

124. Guanglin Luo, Rembert Pieper, Angela Rosa, Chaitan Khosla, and David E. Cane, "Erythromycin Biosynthesis: Exploiting the Catalytic Versatility of the Modular Polyketide Synthase," Bioorganic Med. Chem. 74, 995-999 (1996).

125. Rembert Pieper, Camilla Kao, Chaitan Khosla, Guanglin Luo and David E. Cane, "Specificity and Versatility in Erythromycin Biosynthesis," Chem. Soc. Rev. 25, 297-302 (1996).

126. Alison Hill, David E. Cane, Christopher J. D. Mau, and Charles A. West, "Heterologous Overexpression and Characterization of ," Arch. Biochem. Biophys 336, 283-289 (1996).

127. Camilla M. Kao, Guanglin Luo, Leonard Katz, David E. Cane, and Chaitan Khosla, "Engineered Biosynthesis of Structurally Diverse Tetraketides by a Trimodular Polyketide Synthase, " J. Am. Chem. Soc. 118, 9184-9185 (1996).

128. David E. Cane, Qun Xue, and Brian C. Fitzsimons, "Trichodiene Synthase. Probing the Role of the Highly Conserved Aspartate-Rich Region by Site-Directed Mutagenesis," Biochemistry, 35, 12369-12376 (1996).

129. David E. Cane, Qun Xue, and James E. Van Epp, "Enzymatic Formation of Isochamigrene, a Novel Sesquiterpene, by Alteration of the Aspartate-Rich Region of Trichodiene Synthase," J. Am. Chem. Soc. 118, 8499-8500 (1996).

130. David E. Cane and Youla S. Tsantrizos, "Aristolochene Synthase. Elucidation of the Cryptic Germacrene A Synthase Activity Using the Anomalous Substrate Dihydrofarnesyl Diphosphate," J. Am. Chem. Soc. 118, 10037-10040 (1996).

131. David Bedford, John R. Jacobsen, Guanglin Luo, David E. Cane, and Chaitan Khosla, "A Functional Chimeric Modular Polyketide Synthase Generated via Domain Replacement," Chem. Biol., 3, 827-831 (1996).

132. Camilla M. Kao, Rembert Pieper, David E. Cane, and Chaitan Khosla, "Evidence for Two Catalytically Independent Clusters of Active Sites in a Functional Modular Polyketide Synthase," Biochemistry 35, 12363- 12368 (1996).

133. Naohiro Tsukamoto, Jo-Anne Chuck, Guanglin Luo, Camilla M. Kao, Chaitan Khosla, and David E. Cane, "6- Deoxyerythronolide B synthase 1 is specifically acylated by a diketide intermediate at the β-ketoacyl-ACP synthase domain of module 2," Biochemistry 35, 15244-15248 (1996).

134. Rembert Pieper, Rajesh S. Gokhale, Guanglin Luo, David E. Cane, and Chaitan Khosla, "Purification and Characterization of Bimodular and Trimodular Derivatives of the Erythromycin Polyketide Synthase," Biochemistry, 36, 1846-1851 (1997).

135. David E. Cane, Hsien-Tai Chiu, Po-Huang Liang, and Karen S. Anderson, "A Pre-Steady State Kinetic Analysis of the Trichodiene Synthase Reaction Pathway," Biochemistry, 36 , 8332 -8339 (1997).

136. Robert McDaniel, Camilla M. Kao, Hong Fu, Peter Hevezi, Claes Gustafsson, Mary Betlach, Gary Ashley, David E. Cane, and Chaitan Khosla, "Gain-of-Function Mutagenesis of the Erythromycin Polyketide Synthase," J. Am. Chem. Soc., 119, 4309-4310 (1997).

8 137. John R. Jacobsen, C. Richard Hutchinson, David E. Cane, and Chaitan Khosla, "Precursor Directed Biosynthesis of Novel Erythromycin Analogs by an Engineered Polyketide Synthase," Science, 277, 367-369 (1997).

138. Charles A. Lesburg, Guangzhi Zhai, David E. Cane and David W. Christianson, "Crystal Structure of Pentalenene Synthase Reveals Novel Active Site Features required for the Mechanism of Terpenoid Cyclization," Science, 277, 1820-1824 (1997).

139. David E. Cane, "Sesquiterpene Biosynthesis. Cyclization Mechanisms," in "Isoprenoids, Including Carotenoids and Steroids," ed., David E. Cane, "Comprehensive Natural Products Chemistry," Vol. 2, Elsevier, London, 1999; pp. 155-200.

140. David E. Cane, "Isoprenoid Biosynthesis. Overview," in "Isoprenoids, Including Carotenoids and Steroids," ed., David E. Cane, "Comprehensive Natural Products Chemistry," Vol. 2, Elsevier, London, 1999; pp. 1-13.

141. David E. Cane, Editor, "Isoprenoids, Including Carotenoids and Steroids. Comprehensive Natural Products Chemistry," Vol. 2, Elsevier, London, 1999.

142. Rajesh S. Gokhale, Janice Lau, David E. Cane, and Chaitan Khosla, "Functional Orientation of the Acyl Domain in a Module of the Erythromycin Polyketide Synthase," Biochemistry 37, 2524-2528 (1998).

143. Camilla M. Kao, Mike McPherson, Robert N. McDaniel, Hong Fu, David E. Cane, and Chaitan Khosla, "Gain of Function Mutagenesis of the Erythromycin Polyketide Synthase. II. Engineered Biosynthesis of an Eight- Membered Tetraketide Lactone," J. Am. Chem. Soc. 119, 11339-11340 (1997).

144. Jo-Anne Chuck, Michael McPherson, Hai Huang, John R. Jacobsen, Chaitan Khosla, and David E. Cane, "Molecular recognition of diketide substrates by a b-ketoacyl-ACP synthase domain within a bimodular polyketide synthase," Chem. Biol. 4, 757-766 (1997).

145. Camilla M. Kao, Michael McPherson, Robert N. McDaniel, Hong Fu, David E. Cane, and Chaitan Khosla, "Alcohol Stereochemistry in Polyketide Backbones is Controlled by the β-Ketoreductase Domains of Modular Polyketide Synthases," J. Am. Chem. Soc. 120, 2478-2479 (1998).

146. David E. Cane, Guest Editor, Chem. Reviews, "Polyketide and Nonribosomal Polypeptide Synthesis," 97 (7) (1997).

147. David E. Cane, "Polyketide and Nonribosomal Polypeptide Synthesis, From Collie to Coli" Chem. Reviews 97, 2463-2464 (1997).

148. John R. Jacobsen, David E. Cane, and Chaitan Khosla, "Spontaneous Decarboxylative Priming of a Downstream Module in 6-Deoxyerythronolide B Synthase," Biochemistry 37, 4928-4934 (1998).

149. David E. Cane, Yuju Hsiung, Julie A. Cornish, J. Kenneth Robinson, and Ian D. Spenser, "Biosynthesis of Vitamin B6: The Oxidation of 4-Hydroxy-L-threonine 4-Phosphate by PdxA," J. Am .Chem. Soc. 120, 1936- 1937 (1998).

150. David E. Cane and Edmund I. Graziani, "Methymycin Biosynthesis. Isolation of P450 Monooxygenase Activity in a Cell-Free System from Streptomyces venezuelae," J. Am. Chem. Soc., 120, 2682-2683 (1998).

151. Michael McPherson, Chaitan Khosla, and David E. Cane, "Erythromycin Biosynthesis: The β-Ketoreductase Domains Catalyze the Stereospecific Transfer of the 4-pro-S Hydride of NADPH," J. Am. Chem. Soc. 120, 3267-3268 (1998).

152. John R. Jacobsen, Adrian Keatinge-Clay, David E. Cane, and Chaitan Khosla, "Precursor-Directed Biosynthesis of 12-Ethyl Erythromycin," Bioorg. Med. Chem. 6, 1171-1177 (1998).

9 153. John R. Jacobsen, David E. Cane, and Chaitan Khosla, "Dissecting the Evolutionary Relationship Between 14- Membered and 16-Membered Macrolides," J. Am. Chem. Soc., 120, 9096-9097 (1998).

154. Janice Lau, Hong Fu, David E. Cane, and Chaitan Khosla, "Dissecting the Role of Acyltransferase Domains of Modular Polyketide Synthases in the Choice and Stereochemical Fate of Extender Units," Biochemistry 38, 1643-1651 (1999).

155. David E. Cane, Christopher T. Walsh, and Chaitan Khosla, “Harnessing the Biogenetic Code: Combinations, Permutations, and Mutations,” Science, 282, 63-68 (1998).

156. Edmund I. Graziani, David E. Cane, Melanie C. Betlach, James T. Kealey, and Robert McDaniel, “Macrolide Biosynthesis: A Single Cytochrome P450, PicK, is Responsible for the Hydroxylations that Generate Methymycin, Neomethymycin, and Picromycin in Streptomyces venezuelae,” Bioorg. Med. Chem. Letters, 8, 3117-3120 (1998).

157. Chaitan Khosla, Rajesh S. Gokhale, John R. Jacobsen, and David E. Cane, “Tolerance and Specificity of Polyketide Synthases,” Ann. Rev. Biochem. 68, 219-253 (1999).

158. Nicola L. Pohl, Rajesh S. Gokhale, David E. Cane, and Chaitan Khosla, “Synthesis and Incorporation of an N- Acetyl Cysteamine Analog of Methylmalonyl-CoA by a Modular Polyketide Synthase,” J. Am. Chem. Soc. 120, 11206-11207 (1998).

159. Rajesh S. Gokhale, Daniel Hunziker, David E. Cane, and Chaitan Khosla, “Mechanism and Specificity of the Terminal Thioesterase Domain from the Erythromycin Polyketide Synthase,” Chemistry & Biology, 6, 117-125 (1999).

160. Myriam Seemann, Guangzhi Zhai, Kazuo Umezawa and David Cane, “Pentalenene Synthase. Histidine-309 is Not Required for Catalytic Activity,” J. Am. Chem. Soc. 121, 591-592 (1999).

161. Daniel Hunziker, Nicholas Wu, Kenji Kinoshita, David E. Cane, and Chaitan Khosla, “Precursor Directed Biosynthesis of Novel 6-Deoxyerythronolide B Analogs Containing Non-natural Oxygen Substituents and Reactive Functionalities,” Tetrahedron Lett 40, 635-638 (1999).

162. Rajesh S. Gokhale, Stuart Y. Tsuji, David E. Cane, and Chaitan Khosla, “Dissecting and exploiting Intermodular Communication in Polyketide Synthases,” Science, 284, 482-485 (1999).

163. David E. Cane and Todd E. Bowser, “Trichodiene Synthase. Mechanism-Based Inhibition Of A Sesquiterpene Cyclase,” Bioorg. Med. Chem. Lett. 9, 1127-1132 (1999).

164. David E. Cane, Shoucheng Du, J. Kenneth Robinson, Yuju Hsiung, and Ian D. Spenser, “Biosynthesis of Vitamin B6. Enzymatic Conversion of 1-Deoxy-D-xylulose-5-phosphate to Pyridoxol Phosphate,” J. Am. Chem. Soc. 121, 7722-7723 (1999).

165. David E. Cane and Christopher T. Walsh, “Crosstalk: The Parallel and Convergent Universes of Polyketide Synthases and Nonribosomal Peptide Synthetases,” Chemistry & Biology 6, R319-R325 (1999).

166. David E. Cane and Ning Ke, “Epicubenol Synthase. Origin Of The Oxygen Atom Of A Bacterial Sesquiterpene Alcohol,” Bioorg. Med. Chem. Lett. 10, 105-107 (2000).

167. Jonathan M. Caruthers, Ilgu Kang, Michael J. Rynkiewicz, David E. Cane, and David W. Christianson, “Crystal Structure Determination of Aristolochene Synthase from the Blue Cheese Mold, Penicillium roqueforti,” J. Biol. Chem. 275, 25533-25539 (2000).

168. David E. Cane and Ilgu Kang, “Aristolochene Synthase. Purification, Molecular Cloning, High-Level Expression in Escherichia coli, and Characterization of the Aspergillus terreus Cyclase,” Arch. Biochem. Biophys. 376, 354-364 (2000).

169. David E. Cane, “Biosynthesis Meets Bioinformatics,” Science, 287, 818-819 (2000).

10 170. Nicholas Wu, Fumitaka Kudo, David E. Cane, and Chaitan Khosla, “Analysis of the Molecular Recognition Features of Individual Modules Derived from the Erythromycin Polyketide Synthase,” J. Am. Chem. Soc. 122, 4847-4852 (2000).

171. David E. Cane,* Shoucheng Du, and Ian D. Spenser, “Biosynthesis of Vitamin B6: Origin of the Oxygen Atoms of Pyridoxol Phosphate,” J. Am. Chem. Soc. 122, 4213-4214 (2000).

172. Janice Lau, David E. Cane, and Chaitan Khosla, “Substrate Specificity of the Loading Didomain of the Erythromycin Polyketide Synthase,” Biochemistry 39, 10514-10520 (2000).

173. Felipe Lombo, Blaine Pfeifer, Timothy Leaf, Sally Ou, Y.S. Kim, David E. Cane, Peter Licari, Chaitan Khosla, “Enhancing the Atom Economy of Polyketide Biosynthetic Processes through Metabolic Engineering,” Biotechnology Prog., 17, 612-617 (2001).

174. Chaitan Khosla, Rembert Pieper, Guanglin Luo, David E. Cane, and Camilla Kao, “Method to Produce Novel Polyketides,” United States Patent 6,066,721 (May 23, 2000).

175. Chaitan Khosla, Rembert Pieper, Guanglin Luo, and David E. Cane, “Synthesis of Polyketides from Diketides,” United States Patent 6,080,555 (June 27, 2000).

176. Yifeng Yin, Rajesh Ghokale, Chaitan Khosla, and David E. Cane, “Erythromycin Biosynthesis. The 4-pro-S hydride of NADPH is Utilized for Ketoreduction by Both Module 5 and Module 6 of the 6-Deoxyerythronolide B Synthase,” Bioorg. Med. Chem. Lett. 11, 1477-1479 (2001).

177. Stuart Tsuji, David. E. Cane, and Chaitan Khosla, “Selective Protein-Protein Interactions Direct Channeling of Intermediates Between Polyketide Synthase Modules,” Biochemistry, 40, 2326-2331 (2001).

178. David E. Cane, Cathy Chow, Antonietta Lillo, and Ilgu Kang, “Molecular Cloning, Expression and Characterization of the First Three Genes in the Mevalonate-Independent Isoprenoid Pathway in Streptomyces coelicolor,” Bioorg. Med. Chem. 9, 1467-1477 (2001).

179. Kenji Kinoshita, Paul G Williard, Chaitan Khosla, and David E. Cane, “Precursor–Directed Biosynthesis of 16-Membered Macrolides by the Erythromycin Polyketide Synthase,” J. Am. Chem. Soc. 123, 2495-2502 (2001).

180. Blaine A. Pfeifer, Suzanne J. Admiraal, Hugo Gramajo, David E. Cane and Chaitan Khosla, “Biosynthesis of Complex Polyketides in a Metabolically Engineered Strain of Escherichia coli,” Science 291, 1790-1792 (2001).

181. Stéphane B. Richard, Marianne E. Bowman, Witek Kwiatkowski, Ilgu Kang, Cathy Chow, David E. Cane, and Joseph P. Noel, “Structure of 4-diphosphocytidyl-2-C-methylerythritol synthase involved in mevalonate- independent isoprenoid biosynthesis,” Nature Struct. Biol. , 8, 641-648 (2001).

182. Nicola Pohl, Marcus Hans, Hwan Young Lee, Yu Sam Kim, David E. Cane, Chaitan Khosla, “Remarkably Broad Substrate Tolerance of Malonyl-CoA Synthetase, and Enzyme Capable of Intracellular Synthesis of Polyketide Precursors,” J. Am. Chem. Soc. 123, 5822-5823 (2001).

183. Nicholas Wu, Stuart Y. Tsuji, David E. Cane, and Chaitan Khosla, “Assessing the Balance between Protein- Protein Interactions and Enzyme-Substrate Interactions in the Channeling of Intermediates Between Polyketide Synthase Modules,” J. Am. Chem. Soc., 123,6465-6474 (2001).

184. Huawei Chen, Sarah O’Connor, David E. Cane, Christopher T. Walsh, “Epothilone Biosynthesis: Assembly of the Methythiazolylcarboxy Starter Unit on the EpoB Subunit,” Chem. Biol. 8, 899-912 (2001).

185. Shiou-chuan Tsai, Jolanta Krucinski, Larry Miercke, Rajesh Gokhale, Julian Chen, Paul Foster, David E. Cane, Chaitan Khosla, and Robert Stroud, “Crystal Structure of the Terminal Thioesterase Domain of the Erythromycin Polyketide Synthase: Versatility from a Unique Substrate Channel,” Proc. Natl. Acad. Sci. USA. 98, 14808-14813 (2001).

11 186. Michael J. Rynkiewicz, David E. Cane, and David W. Christianson, “Structure of trichodiene synthase from Fusarium sporotrichioides provides mechanistic inferences on the terpene cyclization cascade,” Proc. Natl. Acad. Sci. USA 98, 13543-13548 (2001).

187. David E. Cane, Fumitaka Kudo, Kenji Kinoshita, and Chaitan Khosla, “Precursor-Directed Biosynthesis. Kinetic Analysis Reveals the Biochemical Basis of the Remarkable Selectivity of the Erythromycin Polyketide Synthase Towards Unsaturated Triketides,” Chem. Biol. 9, 131-142 (2002).

188. Chaitan Khosla, Rembert Pieper, Guanglin Luo, David E. Cane, and Camilla Kao, “Method to Produce Novel Polyketides,” United States Patent 6,261,816 (July 17, 2001).

189. Chaitan Khosla, Rembert Pieper, Guanglin Luo, David E. Cane, and Camilla Kao, “Cell-free Synthesis of Polyketides,” United States Patent 6,274,560 (August 14, 2001).

190. Michael J. Rynkiewicz, David E. Cane, and David W. Christianson, “X-ray crystal structures of D100E trichodiene synthase and its diphosphate complex reveal basis for terpene product diversity,” Biochemistry 41, 1732-1741 ( 2002).

191. Nicholas Wu, David E. Cane, and Chaitan Khosla, “Quantitative Analysis of the Relative Contributions of Donor Acyl Carrier Proteins, Acceptor Ketosynthases, and Linker Regions to Intermodular Transfer of Intermediates in Hybrid Polyketide Synthases,” Biochemistry 41, 5056-5066 (2002).

192. Stéphane B. Richard, Jean-Luc Ferrer, Marianne E. Bowman, Antonietta M. Lillo, Charles N. Tetzlaff, David E. Cane, and Joseph P. Noel, “Structure and Mechanism of 2-C-Methyl-D-Erythritol 2,4-Cyclodiphosphate Synthase. Active Site Architecture Supporting Formation of a Cyclodiphosphate-Containing Isoprenoid Precursor,” J. Biol. Chem. 277, 8667-8672 (2002).

193. Myriam Seemann, Guangzhi Zhai, Jan-Willem de Kraker, Chiana M. Paschall, David W. Christianson, and David E. Cane, “Pentalenene Synthase. Analysis of Active Site Residues by Site-Directed Mutagenesis,” J. Am. Chem. Soc.124, 7681-7689 (2002).

194. Hongxiang Lu, Shiou-Chuan Tsai, Chaitan Khosla, and David E. Cane, “Expression, Site-Directed Mutagenesis, and Steady State Kinetic Analysis of the Terminal Thioesterase Domain of the Methymycin/Picromycin Polyketide Synthase,” Biochemistry 41, 12590-12597 (2002).

195. Shiou-Chuan Tsai, Hongxiang Lu, David E. Cane, Chaitan Khosla, and Robert M. Stroud, “Insights into Channel Architecture and Substrate Specificity from Crystal Structures of Two Macrocycle Forming Thioesterases of Modular Polyketide Synthases,” Biochemistry 41, 12598-12606 (2002).

196. Joanne I Yeh, Shoucheng Du, Ehmke Pohl, and David E. Cane, “Multistate Binding in Pyridoxine 5'- Phosphate Synthase: 1.95 Å Crystal Structure in Complex with 1-deoxy-D-xylulose phosphate,” Biochemistry 41, 11649-11657 (2002).

197. Chaitan Khosla, Rembert Pieper, Guanglin Luo, David E. Cane, and Camilla Kao, “Method to Produce Novel Polyketides,” United States Patent 6,500,960 (December 31, 2002).

198. Antonietta M. Lillo, Charles N. Tetzlaff, Félix J. Sangari, David E. Cane, “Functional Expression and Characterization of EryA, the Erythritol Kinase of Brucella abortus and enzymatic synthesis of L-erythritol-4- phosphate,” Bioorg. Med. Chem. Lett. 13, 737-739 (2003).

199. Grace F. Liou, Janice Lau, David E. Cane, and Chaitan Khosla, “Quantitative Analysis of Loading and Extender Acyltransferases of Modular Polyketide Synthases,” Biochemistry, 42, 200-207 (2003).

200. David E. Cane and Rory M. Watt, “Functional Expression and Mechanistic Characterization of a from Streptomyces coelicolor Implicated in Geosmin Biosynthesis,” Proc. Natl. Acad. Sci. USA, 100, 1547-1551 (2003).

12 201. Marcus Hans, Andreas Hornung, Agnieszka Dziarnowski, David E. Cane and Chaitan Khosla, “Mechanistic Analysis of Acyl Transferase Domain Exchange in Polyketide Synthase Modules,” J. Am. Chem. Soc. 125, 5366-5374 (2003).

202. David E. Cane, “Mechanism and Structure of Biosynthetic . The Biosynthesis of Vitamin B6,” Prelog Lecture, ETH, Laboratorium fur Organische Chemie, November 11, 2002, Chimia 74, 71-74 (2003).

203. Pawan Kumar, Qing Li, David E. Cane, and Chaitan Khosla, “Intermodular Communication in Modular Polyketide Synthases: Structural and Mutational Analysis of Linker Mediated Protein-Protein Recognition,” J. Am. Chem. Soc. 125, 4097-4102 (2003).

204. Yifeng Yin, Hongxiang Lu, Chaitan Khosla, and David E. Cane, “Expression and Kinetic Analysis of the Substrate Specificity of Modules 5 and 6 of the Picromycin/Methymycin Polyketide Synthase,” J. Am. Chem. Soc. 125, 5671-5676 (2003).

205. Chaitan Khosla, Rembert Pieper, Guanglin Luo, and David E. Cane, “Cell-free Synthesis of Polyketides,” United States Patent 6,531,299 (March 11, 2003).

206. J. Sivaraman, Yunge Li, Jerel Banks, David E. Cane, Miroslaw Cygler, and Allan Matte, “Crystal Structure of E. coli PdxA, an Enzyme Involved in the Pyridoxal Phosphate Biosynthesis Pathway,” J. Biol. Chem. 278, 43682-43690 (2003).

207. Kenji Kinoshita, Blaine A. Pfeifer, Chaitan Khosla, and David E. Cane, “Precursor-Directed Polyketide Biosynthesis in E. coli,” Bioorg. Med. Chem. Lett. 13, 3701-3704 (2003).

208. Pawan Kumar, Andrew T. Koppisch, David E. Cane and Chaitan Khosla, “Enhancing the Modularity of the Modular Polyketide Synthases: Transacylation in Modular Polyketide Synthases Catalyzed by Malonyl- CoA:ACP Transacylase,” J. Am. Chem. Soc. 125, 14307-14312 (2003).

209. Kenji Kinoshita, Chaitan Khosla, and David E. Cane, “Precursor-Directed Biosynthesis: Stereospecificity for Branched-Chain Diketides of the β-Ketoacyl-ACP Synthase Domain 2 of 6-Deoxyerythronolide B Synthase,” Helv. Chim. Acta 86, 3889-3905 (2003).

210. Kenji Watanabe, Clay C. C. Wang, Christopher N. Boddy, David E. Cane, and Chaitan Khosla, “Understanding Substrate Specificity of Polyketide Synthase Modules by Generating Hybrid Multimodular Synthases,” J. Biol. Chem. 278, 42020-42026 (2003).

211. Xiaofei He and David E. Cane, “Mechanism and Stereochemistry of the Germacradienol/Germacrene D Synthase of Streptomyces coelicolor A3(2)” J. Am. Chem. Soc. 126, 2678-2679 (2004).

212. Jerel Banks and David E. Cane, “Biosynthesis of Vitamin B6: Direct Identification of the Product of the PdxA- Catalyzed Oxidation of 4-Hydroxy-L-threonine-4-phosphate Using Electrospray Ionization Mass Spectrometry,” Bioorg. Med. Chem. Lett. 14, 1633-1636 (2004).

213. Brunella Felicetti and David E. Cane, “Aristolochene Synthase. Mechanistic Analysis of Active Site Residues by Site-Directed Mutagenesis,” J. Am. Chem. Soc. 126, 7212-7221 (2004).

214. Chaitan Khosla, Rembert Pieper, Guanglin Luo, David E. Cane, Camilla Kao, and Gary Ashley “Method to Produce Novel Polyketides,” United States Patent 6,710,189 (March 23, 2004).

215. Chaitan Khosla, Rembert Pieper, Guanglin Luo, and David E. Cane, “Cell Free Synthesis of Polyketides,” United States Patent 6,750,040 (June 15, 2004).

216. David E. Cane, “Back to Basics: Assigning Biochemical Function in the Post-Genomic Era,” Chemistry & Biology, 11, 741-743 (2004).

13 217. Stéphane B. Richard, Antonietta M. Lillo, Charles N. Tetzlaff, Marianne E. Bowman, Joseph P. Noel, and David E. Cane, “Kinetic analysis of E. coli 2-C-methyl-D-erythritol-4-phosphate cytidyltransferase (YgbP), wild-type and mutants, reveals roles of active site amino acids,” Biochemistry, 43, 12189-12197 (2004).

218. Chu-Young Kim, Viktor Y. Alekseyev, Alice Y. Chen, Yinyan Tang, David E. Cane, and Chaitan Khosla, “Reconstituting Modular Activity from Separated Domains of 6-deoxyerythronolide B Synthase,” Biochemistry 43, 13892-13898 (2004).

219. Jiaquan Wu, Kenji Kinoshita, Chaitan Khosla, and David E. Cane, “Biochemical Analysis of Substrate Specificity of the β-Ketoacyl-Acyl Carrier Protein Synthase Domain of Module 2 of the Erythromycin Polyketide Synthase,” Biochemistry 43, 16301-16310 (2004).

220. L. Sangeetha Vedula, Michael J. Rynkiewicz, Hyung-Jung Pyun, Robert M. Coates, David E. Cane, and David W. Christianson, “Molecular Recognition of the Substrate Diphosphate Group Governs Product Diversity in Trichodiene Synthase Mutants,” Biochemistry 44, 6153-6163 (2005).

221. David A. Moffet, Chaitan Khosla, and David E. Cane, “Modular Polyketide Synthases: Investigating Intermodular Communication Using 6-Deoxyerythronolide B Synthase Module 2” Bioorganic Med. Chem. Lett. 16, 213-216 (2006).

222. Weiguo He, Jiaquan Wu, Chaitan Khosla, and David E. Cane “Macrolactonization to 10-Deoxymethynolide Catalyzed by the Recombinant Thioesterase of the Picromycin/Methymycin Polyketide Synthase” Bioorganic Med. Chem. Lett. 16, 391-394 (2006).

223. L. Sangeetha Vedula, David E. Cane, and David W. Christianson, “Role of Arginine-304 in the Diphosphate- Triggered Active Site Closure Mechanism of Trichodiene Synthase,”Biochemistry, 44, 12719-12727 (2005).

224. Sarah Picaud, Per Mercke, Xiaofei, Olov Sterner, Maria Brodelius, David Cane, and Peter E. Brodelius,“ Amorpha-4,11-diene synthase. Mechanism and stereochemistry of the enzymatic cyclization of farnesyl diphosphate,” Arch. Biochem. Biophys. 448, 150-155 (2006).

225. Nathan A. Schnarr, Alice Y. Chen, David E. Cane, and Chaitan Khosla, “Analysis of Covalently Bound Polyketide Intermediates on the 6-Deoxyerythronolide B synthase by Tandem Proteolysis - Mass Spectrometry,” Biochemistry, 44, 11836-11842 (2005).

226. David E. Cane, “Brushes with Sage,” Arch. Biochem. Biophys. 448, 117-122 (2006).

227. Jiaquan Wu, Weiguo He, Chaitan Khosla, and David E. Cane, “Chain-Elongation, Macrolactonization, and Hydrolysis of Natural and Reduced Hexaketide Substrates by the Picromycin/Methymycin Polyketide Synthase,” Angew. Chemie Intl. Ed.44, 7557-7560 (2005).

228. Jiaquan Wu, Toby J. Zaleski, Chiara Valenzano, Chaitan Khosla, and David E. Cane, “Polyketide Double Bond Biosynthesis. Mechanistic Analysis of the -Containing Module of the Picromycin/Methymycin Polyketide Synthase,” J. Am. Chem. Soc. 127, 17393-17404 (2005).

229. Alice Y. Chen, Nathan A. Schnarr, Chu-Young Kim, David E. Cane, and Chaitan Khosla “Extender Unit and Acyl Carrier Protein Specificity of Ketosynthase Domains of the 6-Deoxyerythronolide B Synthase,” J. Am. Chem. Soc. 128, 3067-3074 (2006).

230. Yinyan Tang, Chu-Young, Kim, Irimpan I. Matthews, Alice Y. Chen, David E. Cane, and Chaitan Khosla, “The 2.7 Å Crystal Structure of a 194-kDa Homodimeric Fragment of the 6-Deoxyerythronolide B Synthase,” Proc. Natl. Acad. Sci. USA, 103, 11124-11129 (2006).

231. Charles N. Tetzlaff, Zheng You, David E. Cane, Satoshi Takamatsu, Satoshi Omura and Haruo Ikeda, “A Gene Cluster for Pentalenolactone Biosynthesis in Streptomyces avermitilis,” Biochemistry 45, 6179-6186 (2006).

14 232. Zheng You, Satoshi Omura, Haruo Ikeda, and David E. Cane “Pentalenolactone Biosynthesis. Molecular Cloning and Assignment of Biochemical Function to PtlH, a Non-Heme Iron Dioxygenase of Streptomyces avermitilis,” J. Am. Chem. Soc. 128, 6566-6567 (2006).

233. Xin Lin, Russell Hopson, and David E. Cane, “Genome Mining in Streptomyces coelicolor. Molecular Cloning and Characterization of a New Sesquiterpene Synthase,” J. Am. Chem. Soc. 128, 6022-6023 (2006).

234. David E. Cane, “How to Evolve a Silk Purse From a Sow’s Ear,” Nature Chem. Biol. 2, 179-180 (2006).

235. Jiaoyang Jiang, Xiaofei He, and David E. Cane, “Geosmin Biosynthesis. Streptomyces coelicolor Germacradienol/Germacrene D Synthase Converts Farnesyl Diphosphate to Geosmin,” J. Am. Chem. Soc. 128, 8128-8129 (2006).

236. David E. Cane, Xiaofei He, Seiji Kobayashi, Satoshi Omura, and Haruo Ikeda, “Geosmin Biosynthesis in Streptomyces avermitilis. Molecular Cloning, Expression, and Mechanistic Study of the Germacradienol/Geosmin Synthase,” J. Antibiotics, 59, 471-479 (2006).

237. Richard Quaderer, Satoshi Omura, Haruo Ikeda, and David E. Cane, “Pentalenolactone Biosynthesis. Molecular Cloning and Assignment of Biochemical Function to PtlI, a Cytochrome P450 of Streptomyces avermitilis,” J. Am. Chem. Soc. 128, 13036-13037 (2006).

238. Tiangang Liu, Delin You, Chiara Valenzano, Yuhui Sun, Jialiang Li, Qin Yu, Xiufen Zhou, David E. Cane, Zixin Deng, “Identification of NanE as a Unique Thioesterase for Polyether Chain Release in Nanchangmycin Biosynthesis,” Chem. Biol. 13, 945-955 (2006).

239. Chaitan Khosla, Rembert Pieper, Guanglin Luo, and David E. Cane, “Modified Modular Polyketide Synthase,” United States Patent 7,101,684 (September 5, 2006).

240. Ekaterina Y. Shishova, Luigi Di Constanzo, David E. Cane, and David W. Christianson, “Crystal Structure of Aristolochene Synthase from Aspergillus terreus and the Evolution of Templates for the Cyclization of Farnesyl Diphosphate,” Biochemistry 46, 1941-1951 (2007).

241. Zheng You, Satoshi Omura, Haruo Ikeda, and David E. Cane, “Pentalenolactone biosynthesis. Molecular cloning and assignment of biochemical function to PtlF, a short-chain dehydrogenase from Streptomyces avermitilis, and identification of a new biosynthetic intermediate,” Arch. Biochem. Biophys. 459, 233-240 (2007).

242. Chaitan Khosla, Yinyan Tang, Alice Y. Chen, Nathan A. Schnarr, and David E. Cane, “Structure and Mechanism of the 6-Deoxyerythronolide B Synthase,” Ann. Rev. Biochem. 76, 195-221 (2007).

243. Yinyan Tang, Chu-Young Kim, Alice Y. Chen, David E. Cane, and Chaitan Khosla, “Structural and Mechanistic Analysis of Protein Interactions in Module 3 of the 6-Deoxyerythronolide B Synthase,” Chem. Biol.14, 931-943 (2007).

244. Alice Y. Chen, David E. Cane, and Chaitan Khosla, “Structure-Based Dissociation of a Type I Polyketide Synthase Module” Chem. Biol. 14, 784-792 (2007).

245. Jiaoyang Jiang, Xiaofei He, and David E. Cane, “Biosynthesis of the earthy odorant geosmin by a bifunctional Streptomyces coelicolor enzyme,” Nat. Chem. Biol. 11, 711-715 (2007).

246. L. Sangeetha Vedula, Yuxin Zhao, Robert M. Coates, Tanetoshi Koyama, David E. Cane, and David W. Christianson, “Exploring Biosynthetic Diversity with Trichodiene Synthase,” Arch. Biochem. Biophys. 466, 260-266 (2007).

247. Viktor Y. Alekseyev, Corey W. Liu, David E. Cane, Joseph D. Puglisi, and Chaitan Khosla, “Solution Structure and Proposed Domain-domain Recognition Interface of an Acyl Carrier Protein Domain from a Modular Polyketide Synthase,” Protein. Sci. 16, 2093-2107 (2007).

15 248. L. Sangeetha Vedula, David E. Cane, and David W. Christianson, “Structural and Mechanistic Analysis of Trichodiene Synthase using Site-Directed Mutagenesis: Probing the Catalytic Function of Tyrosine-295 and the Asparagine-225/Serine-229/Glutamate-233–Mg2+ Motif,” Arch. Biochem. Biophys, 469, 184-194 (2008).

249. Roselyne Castonguay, Weiguo He, Alice Y. Chen, Chaitan Khosla, and David E. Cane, “Stereospecificity of Ketoreductase Domains of the 6-Deoxyerythronolide B Synthase,” J. Am. Chem. Soc. 129, 13758-13769 (2007).

250. Zheng You, Satoshi Omura, Haruo Ikeda, David E. Cane, and Gerwald Jogl, “Crystal Structure of the Non- heme Iron Dioxygenase PtlH in Pentalenolactone Biosynthesis,” J. Biol. Chem. 282, 36552-36560 (2007).

251. Bin Zhao, Xin Lin, Li Lei, David C. Lamb, Steven L. Kelly, Michael R. Waterman, and David E. Cane, “Biosynthesis of the Sesquiterpene Antibiotic Albaflavenone in Streptomyces Coelicolor A3(2),” J. Biol. Chem.. 283, 8183-8189 (2008).

252. Ekaterina Y. Shishova, Fanglei Yu, David J. Miller, Juan A. Faraldos, Yuxin Zhao, Robert M. Coates, Rudolf K. Allemann, David E. Cane, and David W. Christianson, “X-ray Crystallographic Studies of Substrate Binding to Aristolochene Synthase Suggest a Metal Binding Sequence for Catalysis,” J. Biol. Chem.. 283, 15431-15439 (2008).

253. Jiaoyang Jiang and David E. Cane, “Geosmin Biosynthesis. Mechanism of the Fragmentation–Rearrangement in the Conversion of Germacradienol to Geosmin,” J. Am. Chem. Soc. 130, 428-429 (2008).

254. Thorben Nawrath, Jeroen S. Dickschat, Rolf Müller, Jiaoyang Jiang, David E. Cane, and Stefan Schulz, “Identification of (8S,9S,10S)-8,10-dimethyl-1-octalin, a key intermediate in the biosynthesis of geosmin in bacteria,” J. Am. Chem. Soc. 130, 430-431 (2008).

255. Shiven Kapur, Andrew Worthington, Yinyan Tang, David E. Cane, Michael D. Burkart, and Chaitan Khosla, “Mechanism based protein cross-linking of domains from the 6-deoxyerythronolide B synthase,” Bioorg. Med. Chem. Lett. 18, 3034-3038 (2008).

256. Tiangang Liu, Xin Lin, Xiufen Zhou, Zixin Deng, and David E. Cane, “Mechanism of Thioesterase-Catalyzed Chain Release in the Biosynthesis of the Polyether Antibiotic Nanchangmycin,” Chem. Biol. 15, 449-458 (2008).

257. Chieh-Mei Wang and David E. Cane, “Biochemistry and Molecular Genetics of the Biosynthesis of the Earthy Odorant Methylisoborneol in Streptomyces coelicolor,” J. Am. Chem. Soc. 130, 8908-8909 (2008).

258. Steven Giglio, Jiaoyang Jiang, Christopher P Saint, David Cane, and Paul T Monis, “Isolation and Characterization of the Gene Associated with Geosmin Production in Cyanobacteria,” Env. Sci. Technol. 42, 8027–8032 (2008).

259. Roselyne Castonguay, Chiara R. Valenzano, Alice Y. Chen, Adrian Keatinge-Clay, Chaitan Khosla, and David E. Cane, “Stereospecificity of Ketoreductase Domains 1 and 2 of the Tylactone Modular Polyketide Synthase,” J. Am. Chem. Soc. 130, 11598-11599 (2008).

260. Cristina Pinedo, Chieh-Mei Wang, Jean-Marc Pradier, Bérengère Dalmais, Mathias Choquer, Pascal Le Pêcheur, Guillaume Morgant, Isidro G. Collado, David E. Cane, Muriel Viaud, “The Sesquiterpene Synthase from the Botrydial Biosynthetic Gene Cluster of the Phytopathogen Botrytis cinerea,” ACS Chem. Biol. 3, 791- 801 (2008).

261. Bin Zhao, Li Lei, Dmitry G. Vassylyev, Xin Lin, David E. Cane, Steven L. Kelly, Hang Yuan, David C. Lamb Michael R. Waterman, “Crystal Structure of Albaflavenone Monooxygenase Containing a Moonlighting Terpene Synthase Active Site,” J. Biol. Chem. 284, 36711-36719 (2009).

262. Tiangang Liu, David E. Cane, Zixin Deng, “The Enzymology of Polyether Biosynthesis,” Meth. Enzymology. 459, 187-214 (2009).

16 263. Chaitan Khosla, Shiven Kapur, and David E. Cane, “Revisiting the Modularity of Modular Polyketide Synthases,” Curr. Opin. Chem. Biol. 13, 135-143 (2009).

264. Xin Lin and David E. Cane, “Biosynthesis of the Sesquiterpene Antibiotic Albaflavenone in Streptomyces coelicolor. Mechanism and Stereochemistry of the Enzymatic Formation of Epi-isozizaene,” J. Am. Chem. Soc. 131, 6332-6333 (2009).

265. Chieh-Mei Wang, Russell Hopson, Xin Lin and David E. Cane “Biosynthesis of the Sesquiterpene Botrydial in Botrytis cinerea. Mechanism and Stereochemistry of the Enzymatic Formation of Presilphiperfolan-8β-ol,” J. Am. Chem. Soc. 131, 8360-8361 (2009).

266. Jiaoyang Jiang, Charles N. Tetzlaff, Satoshi Takamatsu, Masato Iwatsuki, Mamoru Komatsu, Haruo Ikeda, and David E. Cane, “Genome Mining in Streptomyces avermitilis. A Biochemical Baeyer-Villiger Reaction and Discovery of a New Branch of the Pentalenolactone Family Tree,” Biochemistry 48, 6431-6440 (2009).

267. Chiara R. Valenzano, Rachel J. Lawson, Alice Y. Chen, Chaitan Khosla, and David E. Cane, “The Biochemical Basis for Stereochemical Control in Polyketide Biosynthesis,” J. Am. Chem. Soc. 131, 18501-18511 (2009).

268. Julie A. Aaron, Xin Lin, David E. Cane, and David W. Christianson, “Structure of epi-isozizaene synthase from Streptomyces coelicolor A3(2), a platform for engineering new terpenoid cyclization templates,” Biochemistry 49, 1787-1797 (2010).

269. Fong T. Wong, Alice Y. Chen, David E. Cane, and Chaitan Khosla, “Protein-Protein Recognition between Acyltransferases and Acyl Carrier Proteins in Multimodular Polyketide Synthases,” Biochemistry 49, 95-102 (2010).

270. Mamoru Komatsu, Takuma Uchiyama, Satoshi Omura, David E. Cane, and Haruo Ikeda, “Genome-minimized Streptomyces host for the heterologous expression of secondary metabolism,” Proc. Natl. Acad. Sci. U.S.A. 107, 2646-2651 (2010).

271. Satoshi Takamatsu, Xin Lin, Ayako Nara, Mamoru Komatsu, David E. Cane, and Haruo Ikeda, “Activation of a silent sesquiterpenoid biosynthetic pathway in Streptomyces avermitilis controlling epi-isozizaene and albaflavenone biosynthesis and isolation of a new oxidized epi-isozizaene metabolite,” Microb. Biotech. 4, 184- 191 (2011).

272. Wayne K. W. Chou, Immacolata Fanizza, Takuma Uchiyama, Mamoru Komatsu, Haruo Ikeda, and David E. Cane, “Genome mining in Streptomyces avermitilis: Cloning and characterization of SAV_76, the synthase for a new sesquiterpene, avermitilol,” J. Am. Chem. Soc. 132, 8850-8851 (2010).

273. Shiven Kapur, Alice Y. Chen, Satoshi Yuzawa, David E. Cane, Chaitan Khosla, “Molecular Recognition between Ketosynthase and Acyl Carrier Protein Domains of the 6-Deoxyerythronolide B Synthase,” Proc. Natl. Acad. Sci. U.S.A. 107, 22066-22071 (2010).

274. David E. Cane, “Programming of erythromycin biosynthesis by a modular polyketide synthase,” J. Biol. Chem. 285, 27517-27523 (2010).

275. Xun Guo, Tiangang Liu, Chiara R. Valenzano, Zixin Deng, and David E. Cane, “Mechanism and Stereospecificity of a Fully Saturating Polyketide Synthase Module: Nanchangmycin Synthase Module 2 and Its Dehydratase Domain,” J. Am. Chem. Soc. 132, 14694-14696 (2010).

276. Chiara R. Valenzano, Young-Ok You, Ashish Garg, Adrian Keatinge-Clay, Chaitan Khosla, and David E. Cane, “Stereospecificity of the Dehydratase Domain of the Erythromycin Polyketide Synthase,” J. Am. Chem. Soc. 132, 14697-14699 (2010).

277. Satoshi Takamatsu, Lian-Hua Xu, Shinya Fushinobu, Hirofumi Shoun, Mamoru Komatsu, David E. Cane, and Haruo Ikeda, “Pentalenic acid is a shunt metabolite in pentalenolactone family metabolite biosynthesis: Hydroxylation of 1-deoxypentalenic acid mediated by CYP105D7 (SAV_7469) of Streptomyces avermitilis,” J. Antibiot. 64, 65-71 (2011).

17 278. Steven Giglio, Wayne K. W. Chou, Haruo Ikeda, David E. Cane D.E. and Paul T. Monis, “Biosynthesis of 2- methylisoborneol in cyanobacteria,” Environ. Sci. Tech. 45, 992-998 (2011).

279. Ho Young Lee, Colin J. B. Harvey, David E. Cane, and Chaitan Khosla, “Improved Precursor Directed Biosynthesis in E. coli via Directed Evolution,” J. Antibiot. 64, 59-64 (2011).

280. Yunfeng Hu, Wayne K. W. Chou, Russell Hopson, and David E. Cane, “Genome Mining in Streptomyces clavuligerus. Expression and Biochemical Characterization of Two Cryptic Sesquiterpene Cyclases, (-)-δ- Cadinene Synthase and (+)-T-Muurolol Synthase” Chem. Biol. 18, 32-37 (2011).

281. Emma H. Doud, Deborah L. Perlstein, Manuel Wolpert, David E. Cane⊥, Suzanne Walker, “Two distinct mechanisms for TIM barrel prenyltransferases in bacteria,” J. Am. Chem. Soc. 133, 1270-1273 (2011).

282. Myung-Ji Seo, Dongqing Zhu, Saori Endo, Haruo Ikeda, and David E. Cane, “Genome Mining in Streptomyces. Elucidation of the Role of Baeyer-Villiger Monooxygenases and Non-Heme Iron-Dependent Dehydrogenase/Oxygenases in the Final Steps of the Biosynthesis of Pentalenolactone and Neopentalenolactone,” Biochemistry 50, 1739-1754 (2011).

283. Dongqing Zhu, Myung-Ji Seo, Haruo Ikeda, and David E. Cane, “Genome Mining in Streptomyces. Discovery of an Unprecedented P450-Catalyzed Oxidative Rearrangement That is the Final Step in the Biosynthesis of Pentalenolactone,” J. Am. Chem. Soc. 133, 2128-2131 (2011).

284. Louise K. Charkoudian, Corey W. Liu, Stefania Capone, David E. Cane, Antonio Togni, Dieter Seebach, and Chaitan Khosla, “Probing the Interactions of an Acyl Carrier Protein Domain from the 6-Deoxyerythonolide B Synthase,” Protein Sci. 20, 1244-1255 (2011).

285. Wayne K. W. Chou, Haruo Ikeda, and David E. Cane, “Cloning and characterization of Pfl_1841, a 2- methylenebornane synthase in Pseudomonas fluorescens PfO-1,” Tetrahedron 67, 6627-6632 (2011)

286. Fong T. Wong, Xi Jin, Irimpan I. Mathews, David E. Cane, and Chaitan Khosla, “Structure and Mechanism of the trans-Acting Acyltransferase from the Disorazole Synthase,” Biochemistry 50, 6539-6548 (2011).

287. David E. Cane and Haruo Ikeda, “Exploration and Mining of the Bacterial Terpenome,” Acc. Chem. Res. 45, 463-472 (2012).

288. Xun Guo, Tiangang Liu, Zixin Deng, and David E. Cane, “Essential Role of the Donor Acyl Carrier Protein in Stereoselective Chain Translocation to a Fully Reducing Module of the Nanchangmycin Polyketide Synthase,” Biochemistry 51, 879-887 (2012).

289. Shiven Kapur, Brian Lowry, Satoshi Yuzawa, Sanketha Kenthirapalan, Alice Y. Chen, David E. Cane, and Chaitan Khosla, “Reprogramming a Module of the 6-Deoxyerythronolide B Synthase for Iterative Chain Elongation,” Proc. Natl. Acad. Sci. USA, 109, 4110-4115 (2012).

290. Mustafa Köksal, Wayne K. W. Chou, David E. Cane, and David W. Christianson, “Structure of 2- methylisoborneol synthase from Streptomyces coelicolor and implications for the cyclization of a non-canonical C-methylated monoterpenoid substrate,” Biochemistry 51, 3011-3020 (2012).

291. Mustafa Köksal, David E. Cane, and David W. Christianson, “Structure of geranyl diphosphate C- methyltransferase from Streptomyces coelicolor and implications for the mechanism of isoprenoid modification,” Biochemistry, 51, 3003-3010 (2012)..

292. David E. Cane, “Favouring the Unfavoured,” Nature, 483, 285-286 (2012).

293. Satoshi Yuzawa, Shiven Kapur, David E. Cane, and Chaitan Khosla, “Role of a Conserved Arginine Residue in Linkers between the Ketosynthase and Acyltransferase Domains of Multimodular Polyketide Synthases,” Biochemistry 51, 3708-3710 (2012).

18 294. Colin J. B. Harvey, Joseph D. Puglisi, Vijay S. Pande, David E. Cane, and Chaitan Khosla, “Precursor Directed Biosynthesis of an Orthogonally Functional Erythromycin Analog: Selectivity in the Ribosome Macrolide Binding Pocket,” J. Am. Chem. Soc.134, 12259-12265.

295. Liansuo Zu, Meimei Xu, Michael W. Lodewyk, David E. Cane, Reuben J. Peters, and Dean J. Tantillo, “Effect of Isotopically Sensitive Branching on Product Distribution for Pentalenene Synthase – Support for a Mechanism Predicted by Quantum Chemistry,” J. Am. Chem. Soc 134, 11369-11371.

296. Yuuki Yamada, David E. Cane, and Haruo Ikeda, “Diversity and Analysis of Bacterial Terpene Synthases,” Meth. Enzymol. 515, 123-162 (2012).

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