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(12) United States Patent (10) Patent No.: US 7.455,998 B2 Brandstadt Et Al US007455998B2 (12) United States Patent (10) Patent No.: US 7.455,998 B2 Brandstadt et al. (45) Date of Patent: Nov. 25, 2008 (54) METHODS FOR FORMING STRUCTURALLY 2004/OO7781.6 A1 4/2004 Brandstadt et al. DEFINED ORGANIC MOLECULES FOREIGN PATENT DOCUMENTS CA 2422600 * 3f2OO2 (75) Inventors: Kurt Friedrich Brandstadt, WO WO 90,09446 A 8, 1990 Frankenmuth, MI (US); Thomas WO WO 02/22842 A1 3, 2002 Howard Lane, Midland, MI (US); John WO WOO3/O542O5 A2 T 2003 C. Saam, Midland, MI (US); Joseph C. OTHER PUBLICATIONS McAuliffe, Sunnyvale, CA (US) J.N. Cha et al. “Silicatein Filaments and Subunits From a Marine Sponge Direct the Polymerization of Silica and Silcones. In vitro'. (73) Assignees: Dow Corning Corporation, Midland, PNAS 96: 361-365. (Jan. 1999).* MI (US); Genencor International, Inc., 1997 Sigma Catalog, pp. 652-653.* Palo Alto, CA (US) Bassindale et al., Enzyme-catalysed siloxane bond formation, Jour nal of Inorganic Biochemistry, May 21, 2003, pp. 401–406, Elsevier (*) Notice: Subject to any disclaimer, the term of this Inc. patent is extended or adjusted under 35 Fattaklhova et al., Fermentative Hydrolysis of the Silicon-Oxygen Bond, Access Russia, Inc. pp. 100-105. U.S.C. 154(b) by 480 days. Nishino et al., Enzymatic silicon oligomerization catalyzed by a lipid-coated lipase, The Royal Society of Chemistry 2002, pp. 2684 (21) Appl. No.: 10/791.951 2685. Bassindale et al., Biocatalysis of Siloxane Bonds, Polymer Preprints (22) Filed: Mar. 3, 2004 2003, 44(2), pp. 570-571. Bassindale et al: "Siloxane Biocatalysis. Polymer Preprints.” Mid (65) Prior Publication Data Mar. 2004, vol. 45, No. 1, pp. 614-615, see Scheme 3, p. 614. Jamison et al: “Bridged Polygermsesquioxanes. Organically Modi US 2005/O196849 A1 Sep. 8, 2005 fied Germanium Oxide Materials”. Chemical Materials. Sep. 1993, vol. 5, No. 9, pp. 1193-1195, see p. 1194, left column. (51) Int. C. Bassindale et al: “Enzyme-Catalyzed Siloxane Bond Formation”. CI2P 9/00 (2006.01) Journal Inorg. Chem. 2003, vol. 93, pp. 401–406, see Table 1, p. 405. CI 2N 9/76 (2006.01) * cited by examiner CI2N 9/20 (2006.01) CI2N 9/14 (2006.01) Primary Examiner Rebecca E. Prouty (52) U.S. Cl. ....................... 435/131; 435/213: 435/198: (74) Attorney, Agent, or Firm Dinsmore & Shohl LLP 435/195 (57) ABSTRACT (58) Field of Classification Search ....................... None See application file for complete search history. Methods of forming organic molecules comprising contact ingahydrolase enzyme with an organic reactant are provided. (56) References Cited Methods for forming an organosilicon molecule comprising U.S. PATENT DOCUMENTS contacting a hydrolase enzyme with an organosilicon reactant are also provided. 6,617.411 B1 9, 2003 Friedrich 2003/01 1915.6 A1* 6/2003 Sakkab ....................... 435/131 13 Claims, 25 Drawing Sheets U.S. Patent Nov. 25, 2008 Sheet 2 of 25 US 7.455,998 B2 u?sdKu?opnosd Z9.Inã?I () U.S. Patent Nov. 25, 2008 Sheet 3 of 25 US 7.455,998 B2 . (291) oWISOS aw) rig s i "-in ---worn. (8.1) "aOS 9W '9 "-----. s (06) "HOIS 9WW wWeS.N ---ror-ror-revoor---- T "r-y-r-rrera-ry -ror--- i s U.S. Patent Nov. 25, 2008 Sheet 4 of 25 US 7.455,998 B2 i (pelA%) SOWH U.S. Patent Nov. 25, 2008 Sheet 5 Of 25 US 7.455,998 B2 i (pleA%) SOWH U.S. Patent Nov. 25, 2008 Sheet 6 of 25 US 7.455,998 B2 i (pel 96) SCWH U.S. Patent Nov. 25, 2008 Sheet 7 Of 25 US 7.455,998 B2 C O O O CO V N (pleIA%) SOWH U.S. Patent Nov. 25, 2008 Sheet 8 of 25 US 7.455,998 B2 (O)aunqeleduual 89InáH (pel '6) SONH U.S. Patent Nov. 25, 2008 Sheet 9 of 25 US 7.455,998 B2 ra E C CN s . C. 2. did 5 o S G C 5 O O 8gS.3 i 2 O O O O O O L) w cy CN w (fuff) Almov U.S. Patent Nov. 25, 2008 Sheet 10 of 25 US 7.455,998 B2 9. O CD s i enoelow peset-uoolS U.S. Patent Nov. 25, 2008 Sheet 11 of 25 US 7.455,998 B2 0009Z 0000Z 0009||0000|| II9.InáI 0009 (pleA96) SOWH U.S. Patent Nov. 25, 2008 Sheet 12 of 25 US 7.455,998 B2 > ... O O. v. O O w en m y S.C S s Er o 3. (n > an O V O O O O O O O r CN re (fu/n) Almov U.S. Patent Nov. 25, 2008 Sheet 13 Of 25 US 7.455,998 B2 SIH•! U.S. Patent Nov. 25, 2008 Sheet 14 of 25 US 7.455,998 B2 --bOvine -0-recombinant bovine -a-porcine -o-, Atlantic COd Figure 14 U.S. Patent Nov. 25, 2008 Sheet 15 of 25 US 7.455,998 B2 100 Control trypsin Figure 15 U.S. Patent Nov. 25, 2008 Sheet 16 of 25 US 7.455,998 B2 ) Figure 16 U.S. Patent Nov. 25, 2008 Sheet 17 of 25 US 7.455,998 B2 hydrolysis Condensation Figure 17 U.S. Patent Nov. 25, 2008 Sheet 18 of 25 US 7.455.998 B2 1 4 --Me3SiOEt --Me3SiOH -- HMDS 0.4 e mass balance O.2 Figure 18 U.S. Patent Nov. 25, 2008 Sheet 19 of 25 US 7.455,998 B2 0.6 0. 5 O. 4 0. 3 0. 2 0. 1 O hydrolysis Condensation Figure 19 U.S. Patent Nov. 25, 2008 Sheet 20 of 25 US 7.455,998 B2 100 80 r 5 trypsin-hydrolysis 60 Control-hydrolysis & 40 trypsin-condensation SS OControl-Condensation 20 U.S. Patent Nov. 25, 2008 Sheet 21 of 25 US 7.455,998 B2 trypsin-hydrolysis control-hydrolysis trypsin-condensation O Control-Condensation Figure 21 U.S. Patent Nov. 25, 2008 Sheet 22 of 25 US 7.455,998 B2 trypsin-hydrolysis control-hydrolysis 3 trypsin-condensation OControl-condensation Me3SiOEt Me2Si(CH2)4O) Figure 22 U.S. Patent Nov. 25, 2008 Sheet 23 Of 25 US 7.455,998 B2 hydrolysis Condensation Figure 23 U.S. Patent Nov. 25, 2008 Sheet 24 of 25 US 7.455,998 B2 1OO - 8O 9 60 : hydrolysis is: 40 Condensation SS Figure 24 U.S. Patent Nov. 25, 2008 Sheet 25 Of 25 US 7.455,998 B2 original 20 mM CaCl2 Figure 25 US 7,455,998 B2 1. METHODS FOR FORMING STRUCTURALLY DEFINED ORGANIC MOLECULES FIELD OF THE INVENTION R R (R')4, Si(OR), or ( SiV O : O1 Si N. R-O Z The present invention relates to methods for forming R4 organic molecules, and more particularly, to methods for forming organic molecules comprising contacting a hydro lase enzyme with an organic reactant. wherein: R' is selected from the group consisting of alkyl, 10 haloalkyl, unsaturated alkyl, aryl, alcohol, epoxy, ether, BACKGROUND OF THE INVENTION amine, (OSiR), OSiR, and a combination thereof; Ri is selected from the group consisting of alkyl, hydrogen, ether The biomolecular mechanisms of numerous organic mol and a combination thereof; R is selected from the group ecules are essentially undefined. Particularly, the organic consisting of alkyl, unsaturated alkyl, aryl, hydrogen and a molecules containing silicon are essential for growth and 15 combination thereof; R is selected from the group consisting biological function in a variety of plant, animal, and microbial of alkyl, haloalkyl, unsaturated alkyl, aryl, hydrogen, systems, however the molecular mechanism for these inter hydroxy, alkoxy, alcohol, epoxy, ether, amine. —(OSiR-2), actions are effectively unknown. The in vitro studies of natu OSiR and a combination thereof; n is an integer from 0 to 4; ral systems within the area of silicabiosynthesis are compli y is 0 or an integer greater than 0; and Z is 3 or is an integer cated. Early mechanistic queries including biomimetic greater than 3. The hydrolase enzyme comprises lipase, pro approaches often failed to recognize the chemistry of silicic tease, phosphoesterase, esterase, cutinase or a combination acid and its analogues. For example, silicatein was deter thereof. The hydrolase enzyme catalyzes the hydrolysis and mined to catalyze the polycondensation of tetraethoxysilane condensation of the organosilicon reactant to form the orga during the formation of particulate silica. However, given the nosilicon molecule. limitations of the product and the resultant analysis, the study 25 In yet another embodiment of the present invention, a was notable to differentiate between the role of silicatein in method of forming an organosilicon intermediate molecule is the hydrolysis and condensation reactions during biosilicifi provided. The method comprises contacting a hydrolase cation. enzyme with an organosilicon reactant. The organosilicon Thus, there remains a need for improved methods of form reactant comprises the formula: ing structurally defined organic molecules and materials, par 30 ticularly organosilicon molecules. SUMMARY OF THE INVENTION RR (R')4, Si(OR), or ( SiV O : O1 Si N. Accordingly, the present invention is directed to methods 35 R-O Z of forming an organic molecule. The method comprises con R4 tacting a hydrolase enzyme with an organic reactant. The organic reactant comprises the formula: wherein: R' is selected from the group consisting of alkyl, 40 haloalkyl, unsaturated alkyl, aryl, alcohol, epoxy, ether, amine, —(OSiR.), OSiR's, and a combination thereof; R is selected from the group consisting of alkyl, hydrogen, ether (R')4-X(OR), or X O : X and a combination thereof; R is selected from the group No-s.R4 consisting of alkyl, unsaturated alkyl, aryl, hydrogen and a 45 combination thereof; R is selected from the group consisting of alkyl, haloalkyl, unsaturated alkyl, aryl, hydrogen, wherein X is selected from the group consisting of silicon and hydroxy, alkoxy, alcohol, epoxy, ether, amine.
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