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The synthesis of specifically 14 C‐labelled 2,6‐diaminopimelic acid and its higher homologues
Author(s) -
Hanuš J.,
Vereš K.
Publication year - 1970
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590060205
Subject(s) - alkylation , diaminopimelic acid , chemistry , hydrolysis , condensation , acid hydrolysis , organic chemistry , medicinal chemistry , catalysis , enzyme , physics , peptidoglycan , thermodynamics
D,L‐2,6‐Diaminopimelic‐(2‐ 14 C) acid was prepared by alkylation of diethyl acetamidomalonate‐(2‐ 14 C) with 5‐bromo‐N‐phthaloyl‐L‐norvaline methyl ester and hydrolysis of the condensation product. Depending on the alkylation conditions, partial or complete racemisation takes place and therefore the L,L‐form of diaminopimelic acid had to be isolated by paper chromatography. Alkylation of diethyl acetamidomalonate‐(2‐ 14 C) with diethyl 4‐bromobutyl‐ or 5‐bromopentyl‐ or 6‐bromohexylacetamidomalonate and subsequent hydrolysis of the condensation products gave D,L‐2,7‐diamino‐suberic‐(2‐ 14 C), D,L‐2,8‐diaminoazelaic‐2‐ 14 C, and D,L‐2,8‐diaminosebacic‐(2‐ 14 C) acids respectively.