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Syntheses of 14 C‐mustard‐labelled and 14 C‐leucine‐labelled Asaley
Author(s) -
Farquhar D.,
Lu K.,
Loo T. L.
Publication year - 1980
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580170202
Subject(s) - chemistry , thionyl chloride , moiety , leucine , ethylene oxide , chloride , organic chemistry , stereochemistry , medicinal chemistry , amino acid , biochemistry , copolymer , polymer
The synthesis of Asaley labelled with 14 C in the mustard (Asaley‐must‐ 14 C) or the leucine (Asaley‐leu‐ 14 C) moiety is described. In the former, ethyl pamino‐N α ‐acetyl‐DL‐phenylalanyl‐L‐leucinate was reacted with ethylene oxide(U)‐ 14 C to give the bis(hydroxyethyl)amino analogue, which was converted to Asaley by treatment with thionyl chloride. Asaley labelled in the leucine moiety was prepared by condensation of N‐acetylsarcolysin with ethyl leucinate(U)‐ 14 C in the presence of dicyclohexylcarbodiimide. The identity of the products was established by spectroscopic, chemical, and chromatographic techniques.