STUDIES ON CEPHEM SULFONES AS MECHANISM-BASED INACTIVATORS OF HUMAN-LEUKOCYTE ELASTASE .3. REACTIONS ENSUING FROM CHEMICAL BETA-LACTAM CLEAVAGE

Authors
ALPEGIANI M BISSOLINO P BORGHI D RIZZO V PERRONE E
Citation
M. Alpegiani et al., STUDIES ON CEPHEM SULFONES AS MECHANISM-BASED INACTIVATORS OF HUMAN-LEUKOCYTE ELASTASE .3. REACTIONS ENSUING FROM CHEMICAL BETA-LACTAM CLEAVAGE, Bioorganic & medicinal chemistry letters, 3(11), 1993, pp. 2259-2264
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
3
Issue
11
Year of publication
1993
Pages
2259 - 2264
Database
ISI
SICI code
0960-894X(1993)3:11<2259:SOCSAM>2.0.ZU;2-S
Abstract
The molecular events ensuing from beta-lactam cleavage of cephem sulfo nes by chemical nucleophiles have been determined. Alkaline hydrolysis and methanolysis led to opening of the dihydrothiazine ring to produc e sulfinate salts. Cleavages promoted by NaN3, imidazole and n-PrSH in MeCN gave products from dihydrothiazine opening and desulfonylation. By contrast with enzyme-promoted reactions, expulsion of potential lea ving groups at C3' was not observed.