US6136961A
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Biocatalytic methods for synthesizing and identifying biologically active compounds
Assignee: Curia Global Inc
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Filing: 1996-09-11
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Granted: 2000-10-24
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Expires: 2016-09-11
Abstract
Abstract Highly specific biocatalytic reactions have been used to create a population of derivatives from a single starting compound. Examples demonstrate synthesis of derivatives of taxol, taxol-2'-adipate, taxol-2'-vinyl adipate, 2,3-(methylenedioxy) benzaldehyde, (±)-(2-endo, 3-exo)-bicyclo (2.2.2)octo-5-ene-2,3-dimethanol, adenosine and erythromycin.
Inventors
- 👤 Jonathan S. Dordick
- 👤 Douglas S. Clark
- 👤 Peter C. Michels
- 👤 Yuri L. Khmelnitsky
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 12:45
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/02; C07D493/04; C07D305/00; C07D305/14; C07H; C07H13/00; C07H13/02; C07H13/04; C07H13/06; C07H13/08; C07H13/10; C07H15/00; C07H15/18; C07H15/26; C07H17/00; C07H17/04; C07H17/08; C07H19/00; C07H19/02; C07H19/04; C07H19/16
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
95 words
A taxol-2'-adipate derivative of the formula ##STR13## wherein: R 1 is hydrogen, C 1-10 alkyl ester, halosubstituted C 1-10 alkyl ester, or CO(CH 2 ) n COR 3 where n is an integer of 2-10 and R 3 is hydrogen, C 1-10 alkyl or C 1-10 alkenyl; n is an integer of 2-10; and R 2 is hydrogen, C 1-10 alkyl, C 1-10 alkenyl, or a 6 substituted saccharide compound selected from the group consisting of glucose, galactose, allose, altrose, mannose, gulose, idose, talose, lactose, cellobiose, sucrose, fructose, deoxynojirimycin, N-acetyl glucosamine, N-acetyl galactoseamine, and maltose.
Claim 2
Dependent Claim
95 words
A taxol-2'-adipate derivative of the formula ##STR13## wherein: R 1 is hydrogen, C 1-10 alkyl ester, halosubstituted C 1-10 alkyl ester, or CO(CH 2 ) n COR 3 where n is an integer of 2-10 and R 3 is hydrogen, C 1-10 alkyl or C 1-10 alkenyl; n is an integer of 2-10; and R 2 is hydrogen, C 1-10 alkyl, C 1-10 alkenyl, or a 6 substituted saccharide compound selected from the group consisting of glucose, galactose, allose, altrose, mannose, gulose, idose, talose, lactose, cellobiose, sucrose, fructose, deoxynojirimycin, N-acetyl glucosamine, N-acetyl galactoseamine, and maltose.
Claim 3
Dependent Claim
236 words
A derivative of bergenin, of the formula ##STR14## wherein R 4 , R 5 , and R 6 are each independently hydrogen, C 1-10 alkyl ester, C 1-10 alkyl substituted C 1-10 alkyl ester, halosubstituted C 1-10 alkyl ester, C 6-20 aralkyl ester, halo substituted C 6-20 aralkyl ester, C 6-20 aralkenyl ester, a 1 substituted saccharide compound selected from the group consisting of glucose, galactose, allose, altrose, mannose, gulose, idose, talose, lactose, cellobiose, sucrose, fructose, deoxynojirimycin, N-acetyl glucosamine, N-acetyl galactosemine and maltose, or CO(CH2) n COR 10 where n is an integer of 2-10; and R 10 is OH, C 1-10 alkoxy, C 1-10 alkenyloxy, a 6 substituted saccharide compound selected from the group consisting of glucose, galactose, allose, altrose, mannose, gulose, idose, talose, lactose, cellobiose, sucrose, fructose, deoxynojirimycin, N-acetyl glucosamine, N-acetyl galactosemine and maltose, or NR 11 R 12 where R 11 and R 12 are each independently hydrogen, C 1-10 alkyl, C 1-10 alkyl substituted with C 1-10 alkyl, C 4-20 aryl or halogen; R 7 is H, OH, F, Cl, Br, or I; R 9 and R 9 are each independently hydrogen or C 1-10 alkyl, provided that when R 7 is H, R 4 , R 5 and R 6 are not all hydrogen, and that when R 7 is H, R 8 and R 9 are methyl, R 4 , R 5 and R 6 are not acetyl or benzoyl.
Claim 4
Dependent Claim
236 words
A derivative of bergenin, of the formula ##STR14## wherein R 4 , R 5 , and R 6 are each independently hydrogen, C 1-10 alkyl ester, C 1-10 alkyl substituted C 1-10 alkyl ester, halosubstituted C 1-10 alkyl ester, C 6-20 aralkyl ester, halo substituted C 6-20 aralkyl ester, C 6-20 aralkenyl ester, a 1 substituted saccharide compound selected from the group consisting of glucose, galactose, allose, altrose, mannose, gulose, idose, talose, lactose, cellobiose, sucrose, fructose, deoxynojirimycin, N-acetyl glucosamine, N-acetyl galactosemine and maltose, or CO(CH2) n COR 10 where n is an integer of 2-10; and R 10 is OH, C 1-10 alkoxy, C 1-10 alkenyloxy, a 6 substituted saccharide compound selected from the group consisting of glucose, galactose, allose, altrose, mannose, gulose, idose, talose, lactose, cellobiose, sucrose, fructose, deoxynojirimycin, N-acetyl glucosamine, N-acetyl galactosemine and maltose, or NR 11 R 12 where R 11 and R 12 are each independently hydrogen, C 1-10 alkyl, C 1-10 alkyl substituted with C 1-10 alkyl, C 4-20 aryl or halogen; R 7 is H, OH, F, Cl, Br, or I; R 9 and R 9 are each independently hydrogen or C 1-10 alkyl, provided that when R 7 is H, R 4 , R 5 and R 6 are not all hydrogen, and that when R 7 is H, R 8 and R 9 are methyl, R 4 , R 5 and R 6 are not acetyl or benzoyl.
Claim 5
Dependent Claim
132 words
An erythromycin derivative of the formula ##STR15## wherein R 13 is hydrogen or OH; R 14 is CH 3 or CO 2 H; and R 15 is hydrogen or CO(CH 2 ) n COR 16 where n is an integer of 2-10; and R 16 is OH, C 1-10 alkoxy, C 1-10 alkenyloxy, a 6 substituted saccharide compound selected from the group consisting of glucose, galactose, allose, altrose, mannose, gulose, idose, talose, lactose, cellobiose, sucrose, fructose, deoxynojirirmycin, N-acetyl glucosamine, N-acetyl galactosamine, and maltose, or NR 17 R 18 where R 17 and R 18 are each independently hydrogen, C 1-10 alkyl, C 1-10 alkyl substituted with C 1-10 alkyl, C 6-20 aryl or halogen; provided that when R 13 and R 15 are each hydrogen, R 14 is not CH 3 .
Claim 6
Dependent Claim
132 words
An erythromycin derivative of the formula ##STR15## wherein R 13 is hydrogen or OH; R 14 is CH 3 or CO 2 H; and R 15 is hydrogen or CO(CH 2 ) n COR 16 where n is an integer of 2-10; and R 16 is OH, C 1-10 alkoxy, C 1-10 alkenyloxy, a 6 substituted saccharide compound selected from the group consisting of glucose, galactose, allose, altrose, mannose, gulose, idose, talose, lactose, cellobiose, sucrose, fructose, deoxynojirirmycin, N-acetyl glucosamine, N-acetyl galactosamine, and maltose, or NR 17 R 18 where R 17 and R 18 are each independently hydrogen, C 1-10 alkyl, C 1-10 alkyl substituted with C 1-10 alkyl, C 6-20 aryl or halogen; provided that when R 13 and R 15 are each hydrogen, R 14 is not CH 3 .
References Cited (Backward Citations)
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