beta-lactam derivatives as enzyme inhibitors: Peptidic derivatives of (RS)-2-Oxo-4-phenylazetidine-1-alkanoic acids

4-Phenylazetidine-2-one was transformed into 4-phenylazetidine-1-alkanoic acids, which were reacted in the presence of diphenylphosphoroazidate with amino acid esters and dipeptide esters yielding beta-lactam peptides with different spacers between the lactam ring and the peptide moiety. All structu...

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Bibliographic Details
Published inMonatshefte für Chemie Vol. 138; no. 6; pp. 627 - 634
Main Authors Elriati, Ali, Achilles, Karin, Loose, Jutta, Otto, Hans-Hartwig
Format Journal Article
LanguageEnglish
Published WIEN Springer Nature 01.06.2007
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
beta-lactam peptides
beta-lactam 1-alkanoic acids
E-I-COMPLEXES
MECHANISM
HUMAN-LEUKOCYTE ELASTASE
PAPAIN
(S)-4-OXOAZETIDINE-2-CARBOXYLATE
elastase inhibitors
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Summary:4-Phenylazetidine-2-one was transformed into 4-phenylazetidine-1-alkanoic acids, which were reacted in the presence of diphenylphosphoroazidate with amino acid esters and dipeptide esters yielding beta-lactam peptides with different spacers between the lactam ring and the peptide moiety. All structures were established by elementary analyses, HPLC, optical rotation, and spectroscopic data and all new compounds were tested as inhibitors of PPE using standard procedures. Four compounds exhibited a weak activity compared with the standard inhibitor trifluoroacetyl-L-val-L-tyr-L-val.
ISSN:0026-9247
1434-4475
DOI:10.1007/s00706-007-0639-9