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(12) United States Patent (10) Patent No.: US 8,435,765 B2 Abraham Et Al

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(12) United States Patent (10) Patent No.: US 8,435,765 B2 Abraham Et Al USOO84357.65B2 (12) United States Patent (10) Patent No.: US 8,435,765 B2 Abraham et al. (45) Date of Patent: *May 7, 2013 (54) POLYPEPTIDES AND BIOSYNTHETIC 5,994,559 A 1 1/1999 Abushanab et al. PATHWAYS FOR THE PRODUCTION OF 3.35 R 3.399 this et al. MONATIN AND ITS PRECURSORS 6,489,1004. W I B1 12/2002 Liaoat Ka et al. 7,064,219 B2 6/2006 Kawahara et al. (75) Inventors: Timothy W. Abraham, Wayzata, MN 7,390,909 B2 6/2008 Kawahara et al. (US); Douglas C. Cameron, Plymouth, 7.534,898 B2 5/2009 Amino et al. MN (US); Paula M. Hicks, Bend, OR 7,572,607 B2 * 8/2009 Hicks et al. ................... 435/121 (US); Sara C. McFarlan, St Paul MN 7,582.455 B2 * 9/2009 Brazean et al. ............... 435/121 s O O s a wo s 7,781,005 B2 8, 2010 Mori (US); James R. Millis, Plymouth, MN 7,888,081 B2 2/2011 Khare et al. (US); John Rosazza, Iowa City, IA 8,003,361 B2 8/2011 Brady et al. (US); David P. Weiner, Del Mar, CA 8,076,107 B2 12/2011 Buddoo et al. (US); Lishan Zhao, Carlsbad, CA (US) 2003/02284.03 A1 12/2003 Amino et al. s s s 2004/0063175 A1 4/2004 Abraham et al. 2005, 0004394 A1 1/2005 Kawahara et al. (73) Assignee: Cargill, Incorporated, Wayzata, MN 2005.0009153 A1 1/2005 Sugiyama et al. (US) 2005/0020508 A1 1/2005 Amino et al. 2005/OO95670 A1 5/2005 Ikeda et al. (*) Notice: Subject to any disclaimer, the term of this 2005/0106305 A1 5/2005 Abraham et al. patent is extended or adjusted under 35 2005/0112260 Al 5/2005 Abraham et al. U.S.C. 154(b) by 715 days 2005/01 18317 A1 6, 2005 Amino et al. M YW- y yS. 2005, 0137246 A1 6/2005 Amino et al. This patent is Subject to a terminal disis- 2005/01700412005/O153405 A1 7/20058/2005 AbrahamSugiyama et et al. al. Ca10. 2005/0221453 A1 10/2005 Takagi et al. 2005/0221455 A1 10, 2005 McFarlanet al. (21) Appl. No.: 12/124,014 2005/0244937 A1 11/2005 Abraham et al. 2005/0244939 A1 1 1/2005 Sugiyama et al. (22) Filed: May 20, 2008 58.8538 A .338 R.E."ckS et al. O O 2006, OOO3411 A1 1/2006 Sugiyama et al. (65) Prior Publication Data 2006/0003426 A1 1/2006 Sugiyama et al. US 2009/01 17625A1 May 7, 2009 38. A 58 SaiO. ca. O O 2006, OO74249 A1 4/2006 Kawahara et al. Related U.S. Application Data 2006, 0083695 A1 4, 2006 Mori et al. (60) Division- - - of application No. 10/979,821, filed on Nov. 2006/01723962006, O154343 A1 7/20068/2006 MoriSugiyama et al. et al. 3, 2004, which is a continuation-in-part of application No. 10/422,366, filed on Apr. 23, 2003, now (Continued) abandoned. FOREIGN PATENT DOCUMENTS (60) Provisional application No. 60/374,831, filed on Apr. EP O 438314 4f1994 23, 2002. EP O736604 10, 1996 (Continued) (51) Int. Cl. CI2N 9/02 (2006.01) OTHER PUBLICATIONS CI2N L/21 (2006.01) Ackerman, "Structure elucidation of and synthetic approaches to CI2P 13/22 (2006.01) - 52) U.S. C monatin, a metabolite from Schlerochiton ilicifolius.” PhD disserta (52) USPG 435/121435/108:435/193435/69.1 tion, University of Stellenbosch, Jul. 1990. 435/252.3 (Continued) (58) Field of Classification Search .................. 435/121, 435/108, 193, 69.1, 325, 320.1, 252.3; 536/23.2 Primary Examiner — Chih-Min Kam See application file for complete search history. (56) References Cited (57) ABSTRACT U.S. PATENT DOCUMENTS Methods and compositions that can be used to make monatin from glucose, tryptophan, indole-3-lactic acid, indole-3- 3,002,889 A 10, 1961 Kinoshita et al. 3,128.237 A 4, 1964 Motozaki et al. pyruvate, and 2-hydroxy 2-(indol-3-ylmethyl)-4-keto glu 3,399,114 A 8, 1968 Ohsawa et al. taric acid, are provided. Methods are also disclosed for pro 3,751,458 A 8/1973 Wiley ducing the indole-3-pyruvate and 2-hydroxy 2-(indol-3- 4,371,614 A 2, 1983 Anderson et al. ylmethyl)-4-ketoglutaric acid intermediates. Compositions 4,518,692 A 5, 1985 ROZZell 4,975,298 A 12/1990 VanWyket al. provided include nucleic acid molecules, polypeptides, 5,128,164 A 7/1992 VanWyket al. chemical structures, and cells. Methods include invitro and in 5,128,482 A 7, 1992 Olivier et al. Vivo processes, and the in vitro methods include chemical 5,300,437 A 4/1994 Stirling et al. reactions. 5,360,724 A 11/1994 Matcham et al. 5,728,555 A 3/1998 Fotheringham et al. 5,985,617 A 11/1999 Liao 4 Claims, 10 Drawing Sheets US 8,435,765 B2 Page 2 U.S. PATENT DOCUMENTS Bassoli, “Chemistry-Nature, stillan open match for the discovery of 2006/0252135 A1 11/2006 Brazeau et al. new intensive Sweeteners.” Agro FOOD industry hi-tech, 2004, 2007/0099277 A1 5, 2007 Anderson et al. 15(4):27-29. 2007/0105938 A1 5, 2007 Anderson et al. Bassoli et al., “Design and synthesis of new monatin derivatives.” 2008.0020434 A1 1/2008 Braeau et al. 13th International Symposium on Olfaction and Taste (ISOT XIII) 2008.0020435 A1 1/2008 Burke et al. 14th. European Chemoreception Research Organization Congress 2008.0193984 A1 8/2008 Sugiyama et al. (ECRO XIV), Jul. 20-24, 2000, p. 162, Abstract. 2008/0274518 A1 11, 2008 Hicks et al. Bassoli et al., “General Pseudoreceptor Model for Sweet Com 2009,008.8577 A1 4/2009 Buddoo et al. pounds: A Semiquantitative Prediction of Binding Affinity for Sweet 2009,0130285 A1 5, 2009 Abraham et al. Tasting Molecules,” J. Med. Chem., 2002, 45:4402-4409. 2009/O198072 A1 8, 2009 Khare et al. Bassoli et al., “Monatin and Its Stereoisomers: Chemoenzymatic 2011/002O882 A1 1/2011 de Souza et al. Synthesis and Taste Properties.” Eur: J. Org. Chem., 2005, 8:1652 2011/OO45547 A1 2/2011 de Souza et al. 1658. 2011/0300282 Al 12/2011 Brady et al. Bhatnagar et al., “The Broad-specificity, Membrane-bound Lactate 2012,000932.0 A1 1/2012 Evans et al. Dehydrogenase of Neisseria gonorrhoeae: Ties to Aromatic Metabo 2012,0009634 A1 1/2012 Burke et al. lism.” Journal of General Microbiology, 1989, 135:353-360. Bommarius et al., “Some new developments in reductive amination FOREIGN PATENT DOCUMENTS with cofactor regeneration.” Biocatalysis, 1994, 10:37-47. EP 104.5 O29 10, 2000 Bongaerts et al., “Metabolic Engineering for Microbial Production of EP 1445323 8, 2004 Aromatic Amino Acids and Derived Compounds.” Metabolic Engi EP 1449 832 8, 2004 neering, 2001, 3:289-300. EP 1533 376 5, 2005 Brandt and Lindow, "Cloning and characterization of a locus encod EP 1580 268 9, 2005 ing an indolepyruvate decarboxylase involved in indole-3-acetic acid EP 1605 041 12/2005 synthesis in Erwinia herbicola," Appl. Environ. Microbiol. 1996, EP 1350 791 9, 2006 62:4121-4128. EP 1719 758 11, 2006 Buldain et al., “Carbon-13 Nuclear Magnetic Resonance Spectra of JP 2002-060382 8, 2001 the Hydrate, Keto and Enol forms of Oalacetic Acid.” Magn. Res. JP 2003-171365 11, 2001 JP 2001-396471 12/2001 Chem., 1985, 23:478-481. JP 2002-095760 3, 2002 Camargo (Ediclea Cristina Fregonese Camargo), "Preparation of JP 2002-357,043 12/2002 amino acids not proteinogenicos, structurally related to adogante JP 2004-222657 1, 2003 natural Monatina' translated by Google), Jan. 2003, Universidade JP 2004-331644 11, 2003 Estadual de Campinas Instituto de Quimica, Dissertation of Masters. JP 2004-331650 3, 2004 DeLuna et al., “NADP-Glutamate Dehydrogenase Isoenzymes of WO WO 87.01130 2, 1987 Saccharomyces cerevisiae: Purification, Kinetic Properties, and WO WO 89.11212 11, 1989 Physiological Roles,” J. Biol. Chem..., 2001, 276(47):43775-43783. WO WO 99,55877 11, 1999 Eggeling and Sahm, “Amino-acid production: principles of meta WO WOO3,OO913 1, 2003 bolic engineering.” Metabolic Engineering, 1999, Lee & Papoutsakis WO WOO3/45914 6, 2003 eds., Marcel Dekker, Inc., New York. WO WOO3/56026 T 2003 Eikmanns et al., “Cloning, sequence analysis, expression, and inac WO WOO3,598.65 T 2003 WO WOO3,91396 11, 2003 tivation of the Corynebacterium glutamicum iccd gene encoding WO WO 2004/O18672 3, 2004 isocitrate dehydrogenase and biochemical characterization of the WO WO 2004/053.125 6, 2004 enzyme.” J. Bacteriol., 1995, 177:774-782. WO 2004/085624 10, 2004 El-Abyad and Farid, "Optimization of culture conditions for indole WO WO 2005.001105 1, 2005 3-pyruvic acid production by Streptomyces griseoflavus,” Can. J. WO WO 2005/O 14839 2, 2005 Microbiol., 1994, 40:754-760. WO WO 2005/O16022 2, 2005 Flores et al., “Pathway engineering for the production of aromatic WO WO 2005/02O721 3, 2005 compounds in Escherichia coli,' Nature Biotechnology, 1996, WO WO 2005/042756 5, 2005 14:620-623. WO WO 2005/082850 9, 2005 Floydet al., “A Simple Strategy for obtaining both Enantiomers from WO WO 2006/011613 2, 2006 WO WO 2006/113897 10, 2006 an Aldolase Reaction: Preparation of L- and D-4-Hydroxy-2- WO WO 2006/116487 11, 2006 ketoglutarate.” J. Chem. Soc. Perkin Trans. 1, 1992, 1085-1086. WO WO 2007/103389 9, 2007 Fotheringham et al., “The cloning and sequence analysis of the aspC WO WO 2007.1331.83 11, 2007 and tyrB genes from Escherichia coli K12.” Biochem.
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