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US 9,434,968 B2Granted
Transaminase reactions
AssigneeCodexis, Inc.
InventorsGregory Hughes, Paul N. Devine, Fred J. Fleitz, Brendan T. Grau, John Limanto, Christopher Savile, Emily Mundorff
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Abstract
The present disclosure relates to methods of using transaminase polypeptides in the synthesis of chiral amines from prochiral ketones.
Claims10
A process for preparing an amine product of structural formula (I):
- having the indicated stereochemical configuration at the stereogenic center marked with an *;
- in an enantiomeric excess over the opposite enantiomer, wherein R1 is a substituted or unsubstituted aryl or heteroaryl;
- R2 is a substituted or unsubstituted C1-C6 alkyl, —R3C(O)R4, or —R3OC(O)R5;
- R3 is an substituted or unsubstituted C1-C4 alkyl;
- and R4 is H, a substituted or unsubstituted C1-C4 alkyl, NR6R7, or OR8, wherein R5, R6, R7, and R8 are independently H or C1-C4 alkyl;
- the process comprising contacting a ketone substrate of structural formula (II):
- with a transaminase polypeptide in presence of an amino donor under reaction conditions suitable for converting the ketone substrate to the amine product, wherein the transaminase polypeptide has at least 95% sequence identity to SEQ ID NO:74.
4 more elements
A process for preparing the compound of formula (III):
- having the indicated stereochemical configuration at the stereogenic center marked with an * in an enantiomeric excess over the opposite enantiomer, wherein, R10 is Cl, Br, F, CH3, CF3, CN, SO2, —OCH3, or NO2,
- the process comprising:
- (a) contacting a ketone substrate of formula:
- wherein R11 is halogen, OH, —C(O)R4, —OC(O)R5, or NR6R7, wherein R4, R5, R6, and R7 is H or C1-C4 alkyl, and R10 is as defined above, with a transaminase polypeptide in presence of an amino donor under reaction conditions suitable for converting the ketone substrate to an amine product of formula:
- wherein the transaminase polypeptide has at least 95% sequence identity to SEQ ID NO:74;
- and
- (b) cyclizing the amine product under suitable conditions to form the compound of formula (III).
4 more elements
Dependencies are inferred from the claim text.