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The synthesis of specifically 14C-labelled 2,6-diaminopimelic acid and its higher homologues

✍ Scribed by J. Hanuš; K. Vereš


Publisher
John Wiley and Sons
Year
1970
Tongue
French
Weight
398 KB
Volume
6
Category
Article
ISSN
0022-2135

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✦ Synopsis


Abstract

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.


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