CLEAVAGE OF THE 5-AMINO-5-CARBOXY-2-OXAPENTANOYL SIDE-CHAIN FROM ENZYMATICALLY SYNTHESIZED PENICILLINS AND CEPHALOSPORINS

Authors
BALDWIN JE DAVIS SC FORREST AK SCHOFIELD CJ
Citation
Je. Baldwin et al., CLEAVAGE OF THE 5-AMINO-5-CARBOXY-2-OXAPENTANOYL SIDE-CHAIN FROM ENZYMATICALLY SYNTHESIZED PENICILLINS AND CEPHALOSPORINS, Bioorganic & medicinal chemistry letters, 5(21), 1995, pp. 2507-2512
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
5
Issue
21
Year of publication
1995
Pages
2507 - 2512
Database
ISI
SICI code
0960-894X(1995)5:21<2507:COT5SF>2.0.ZU;2-Y
Abstract
Both 5R- and 5S-5-amino-5-carboxy-2-oxapentanoyl side chains can subst itute for the L-delta-alpha-aminoadipoyl side chain in the isopenicill in N synthase catalysed formation of penicillins from tripeptides. The 5R- side chain analogue can be cleaved from penicillins and cephalosp orins by treatment with D-amino acid oxidase followed by oxidative dec arboxylation and decarboxylative elimination.