Synthesis of optically pure mechanism-based inhibitors of γ aminobutyric acid aminotransferase (GABA-T) via enzyme-catalyzed resolution

The kinetic resolution of γ-ethynyl-,γ-allenyl- and γ-vinyl GABA was accomplished by penicillin acylase-catalyzed hydrolysis of their N-phenylacetyl derivatives. The procedure employs inexpensive commercially available immobilized enzyme. A novel enzymatic procedure for the preparation of optically...

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Bibliographic Details
Published inTetrahedron letters Vol. 34; no. 8; pp. 1239 - 1242
Main Author Margolin, Alexey L
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 19.02.1993
Elsevier
Subjects
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Chemistry
Chemistry, Organic
Fundamental and applied biological sciences. Psychology
Methods. Procedures. Technologies
Physical Sciences
Science & Technology
INACTIVATION
SUBSTRATE-SPECIFICITY
AMIDASE
ANALOG
AMINO-ACIDS
ENANTIOMERS
4-AMINOHEX-5-YNOIC ACID
ACYLASE
ENANTIOSELECTIVE HYDROLYSIS
ACCESS
Enzymatic synthesis
Penicillin amidase
Enantioselectivity
Enzyme
Optical resolution
Enzyme inhibitor
4-Aminobutyrate aminotransferase
Immobilized enzyme
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Summary:The kinetic resolution of γ-ethynyl-,γ-allenyl- and γ-vinyl GABA was accomplished by penicillin acylase-catalyzed hydrolysis of their N-phenylacetyl derivatives. The procedure employs inexpensive commercially available immobilized enzyme. A novel enzymatic procedure for the preparation of optically pure γ-ethynyl ( 1)-, γ-allenyl ( 2)- and γ-vinyl ( 3) GABA has been developed.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)91763-5