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Use of enzyme penicillin acylase in selective amidation/amide hydrolysis to resolve ethyl 3-amino-4-pentynoate isomers.

Abstract：

:The beta-amino acid, (S)-ethyl-3-amino-4-pentynoate, is a chiral synthon used in the synthesis of xemilofiban hydrochloride, an anti-platelet agent. A biocatalytic approach was developed to resolve (R)- and (S)-enantiomers of ethyl 3-amino-4-pentynoate in enantiomerically pure form employing the enzyme Penicillin acylase. In the acylation, phenylacetic acid was used as an acylating agent. We have shown that both the acylation and deacylation can be employed and that the activity of the enzyme Penicillin acylase can be controlled by maintaining an appropriate pH of the reaction medium.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Topgi RS,Ng JS,Landis B,Wang P,Behling JR

doi

10.1016/s0968-0896(99)00155-8

subject

Has Abstract

pub_date

1999-10-01 00:00:00

pages

2221-9

issue

10

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(99)00155-8

journal_volume

7

pub_type

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