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Synthesis of the Phenylserine−Leucine Dipeptide Fragment Present in the Antibiotic Lysobactin from an Aziridine‐2‐imide Precursor
Author(s) -
Cardillo Giuliana,
Gentilucci Luca,
Gianotti Massimo,
Tolomelli Alessandra
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200007)2000:13<2489::aid-ejoc2489>3.0.co;2-7
Subject(s) - aziridine , chemistry , dipeptide , imide , oxazoline , leucine , stereochemistry , hydrolysis , amino acid , depsipeptide , fragment (logic) , ring (chemistry) , organic chemistry , biochemistry , catalysis , computer science , programming language
The ring expansion of (2 R′ ,3 S′ ) or (2 S′ ,3 R′ )‐ N ‐(α‐amino acyl)‐aziridine‐2‐imides and the mild hydrolysis of the resulting oxazoline‐4‐imides gives (2 R ,3 S )‐phenylserine−leucine or (2 S ,3 R )‐phenylserine−leucine dipeptides. In particular, the latter fragment is present in the depsipeptide antibiotic Lysobactin.