IP Library Granted Patent US 7,455,998
Granted Patent B2
US 7,455,998 · App. 10/791,951 · Granted Nov 25, 2008

Methods for forming structurally defined organic molecules

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Quick Facts
Patent No.
US 7,455,998
App. No.
10/791,951
Granted
Nov 25, 2008
Kind
B2
Abstract

Methods of forming organic molecules comprising contacting a hydrolase enzyme with an organic reactant are provided. Methods for forming an organosilicon molecule comprising contacting a hydrolase enzyme with an organosilicon reactant are also provided.

Claims (25)

1. A method of forming an organic molecule, comprising contacting a hydrolase enzyme with an organic reactant, wherein:

the organic reactant is selected from the group consisting of:

(CH 3 ) 2 Si(OCH 3 ) 2; (CH 3 )(CF 3 CH 2 CH 2 )Si(OCH 3 ) 2 ; (C 6 H 5 )(CH 3 )Si(OCH 3 ) 2 ; (CH 3 CH 2 ) 2 Ge(OCH 2 CH 3 ) 2 ; (CH 3 )Si(OCH 2 CH 3 ) 3 ; 1,3,5,7-tetramethyl-1,3,5,7-tetramethoxy-cyclotetrasiloxane; 1,3-bis(hydroxy)tetramethyldisiloxane; [(HO) 2 (CH 3 )SiO] 3 SiCH 3 , (Me 3 SiO(CH 2 CH 2 O) 4 CH 3 ), 3-glycidoxypropyldimethylethoxysilane, 1,1-dimethyl-1-sila-2-oxacyclohexane, trimethylsilanol, trimethylethoxysilane or a combination thereof;

the hydrolase enzyme is selected from the group consisting of: Candida antarctica lipase, Candida antarctica lipase B, Rhizomucor miehei lipase, wheat germ lipase, trypsin, cutinase, or a combination thereof; and

the hydrolase enzyme catalyzes the hydrolysis and condensation of the organic reactant to form the organic molecule.

2. The method according to claim 1 , wherein the hydrolase enzyme is trypsin.

3. The method according to claim 1 , wherein the concentration of hydrolase enzyme is equal to or greater than 1 mg/mL.

4. The method according to claim 3 , wherein the concentration of hydrolase enzyme is from about 20 mg/mL to about 60 mg/mL.

5. The method according to claim 1 , wherein the organic reactant to enzyme mole ratio is less than or equal to about 40000:1.

6. The method according to claim 1 , wherein the reaction is conducted at a pH from about 5.0 to about 8.0.

7. The method according to claim 1 , wherein the reaction is conducted in an aqueous solution, or a solvent.

8. The method according to claim 1 , wherein the reaction is conducted at a temperature of between about 5° C. to about 90° C.

9. The method according to claim 8 , wherein the reaction is conducted at a temperature of between about 20° C. to about 50° C.

10. The method according to claim 9 , wherein the reaction is conducted at a temperature of about 25° C.

11. A method of forming an organic intermediate molecule, comprising contacting a hydrolase enzyme with an organic reactant, wherein:

the organic reactant is selected from the group consisting of:

(CH 3 ) 2 Si(OCH 3 ) 2 ; (CH 3 )(CF 3 CH 2 CH 2 )Si(OCH 3 ) 2 ; (C 6 H 5 )(CH 3 )Si(OCH 3 ) 2 ; (CH 3 CH 2 ) 2 Ge(OCH 2 CH 3 ) 2 ; (CH 3 )Si(OCH 2 CH 3 ) 3 ; 1,3,5,7-tetramethyl-1,3,5,7-tetramethoxy-cyclotetrasiloxane; (Me 3 SiO(CH 2 CH 2 O) 4 CH 3 ), 3-glycidoxypropyldimethylethoxysilane, 1,1-dimethyl-1-sila-2-oxacyclohexane, trimethylethoxysilane or a combination thereof,

the hydrolase enzyme is selected from the group consisting of Candida antarctica lipase, Candida antarctica lipase B, Rhizomucor miehei lipase, wheat germ lipase, trypsin, cutinase, or a combination thereof; and

the hydrolase enzyme catalyzes the hydrolysis of the organic reactant to form the organic intermediate molecule.

12. A method of forming an organic molecule, comprising contacting a hydrolase enzyme with an organic intermediate reactant, wherein:

the organic intermediate reactant is selected from the group consisting of:

(CH 3 2 Si(OH) 2 ; (CH 3 )(CF 3 CH 2 CH 2 Si(OH) 2 ; ( 6 H 5 )(CH 3 )Si(OH) 2 ; (CH 3 CH 2 ) 2 Ge(OH) 2 ; (CH 3 )Si(OH) 3 ; 1,3,5,7-tetramethyl-1,3,5,7-tetrahydroxy-cyclotetrasiloxane; 1,3-bis(hydroxy)tetramethyldisiloxane; [(HO) 2 (CH 3 )SiO] 3 SiCH 3, 3-glycidoxypropyldimethylsilanol, HO(CH 2 ) 4 (CH 3 ) 2 SiOH, trimethylsilanol, or a combination thereof,

the hydrolase enzyme is selected from the group consisting of Candida antarctica lipase, Candida antarctica lipase B, Rhizomucor miehei lipase, wheat germ lipase, trypsin, cutinase, or a combination thereof; and

the hydrolase enzyme catalyzes the condensation of the organic intermediate reactant to form the organic molecule.

13. A method of forming an organic molecule, comprising contacting a hydrolase enzyme comprising trypsin, cutinase, or a combination thereof, with an organic reactant selected from the group consisting of: (CH 3 ) 2 Si(OCH 3 ) 2 ; (CH 3 )(CF 3 CH 2 CH 2 )Si(OCH 3 ) 2 ; C 6 H 5 (CH 3 )Si(OCH 3 ) 2 ; (CH 3 CH 2 ) 2 Ge(OCH 2 CH 3 ) 2 ; (CH 3 )Si(OCH 2 CH 3 ) 3 ; 1,3,5,7-tetramethyl-1,3,5,7-tetramethoxy-cyclotetrasiloxane; 1,3-bis(hydroxy)tetramethyldisiloxane; [(HO) 2 (CH 3 )SiO] 3 SiCH 3 , (Me 3 SiO(CH 2 CH 2 O) 4 CH 3 ), 3-glycidoxypropyldimethylethoxysilane, 1,1-dimethyl-1-sila-2-oxacyclohexane, trimethylsilanol, trimethylethoxysilane or a combination thereof; wherein the hydrolase enzyme catalyzes the hydrolysis and condensation of the organic reactant to form the organic molecule.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 22, 2010
From: DANISCO US INC.
To: DOW CORNING CORPORATION
Reel/Frame 024563/0713 →
CHANGE OF NAME Recorded Jun 22, 2010
From: GENENCOR INTERNATIONAL, INC.
To: DANISCO US INC.
Reel/Frame 024563/0718 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 5, 2004
From: MCAULIFFE, JOSEPH C.
To: GENENCOR INTERNATIONAL, INC.
Reel/Frame 014948/0133 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 22, 2004
From: BRANDSTADT, KURT FRIEDRICH; LANE, THOMAS HOWARD; SAAM, JOHN C.
To: DOW CORNING CORPORATION
Reel/Frame 015240/0651 →