BIOCATALYTIC RESOLUTION OF BETA-FLUOROALKYL-BETA-AMINO ACIDS

Citation
Va. Soloshonok et al., BIOCATALYTIC RESOLUTION OF BETA-FLUOROALKYL-BETA-AMINO ACIDS, Tetrahedron : asymmetry, 5(6), 1994, pp. 1119-1126
Citations number
46
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
ISSN journal
09574166
Volume
5
Issue
6
Year of publication
1994
Pages
1119 - 1126
Database
ISI
SICI code
0957-4166(1994)5:6<1119:BROBA>2.0.ZU;2-3
Abstract
N-Phenylacetyl derivatives of beta-fluoroalkyl-beta-alanines 6 were sy nthesized and biocatalytically resolved to the corresponding enantiopu re beta-amino acids 7, 9 with the aid of penicillin acylase (EC 3.5.1. 11) from Escherichia coli. In substrates 6 the enantioselectivity of t he biocatalytic process was practically uninfluenced by the nature of the fluoroalkyl chain. Thus, beta-fluoroalkyl-beta-alanines 7, 9 beari ng short (R = CF3, CHF2) or long [C3F7, H(CF2)(4)] chains were prepare d in high enantiomeric purity. The (R)-enantiomer was the fast-reactin g enantiomer in all cases.