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N‐ acylamino acids and peptides III. The synthesis of N‐ (feruloyl‐2‐ 14 C)‐glycine‐2‐ 3 H
Author(s) -
De Pooter H.,
Pé I.,
Van Sumere C. F.
Publication year - 1974
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.2590100115
Subject(s) - glycine , chemistry , hydrolysis , yield (engineering) , alkaline hydrolysis , ethyl ester , chloride , acylation , amino acid , stereochemistry , medicinal chemistry , nuclear chemistry , organic chemistry , catalysis , biochemistry , metallurgy , materials science
N‐(Feruloyl‐2‐ 14 C)‐glycine‐2‐ 3 H (IX) was obtained with an acceptable yield (43%) starting from O‐methoxycarbonyl‐ferulic acid‐2‐ 14 C (IV) and glycine‐2‐ 3 H ethyl ester (VI). The latter two compounds were first condensed into N‐(O‐methoxycarbonyl‐feruloyl‐2‐ 14 C)‐glycine ‐2‐ 3 H ethyl ester (VII) using anisoyl chloride (X) and the mixed anhydride method (?). Subsequently VII was transformed into N‐(feruloyl‐2‐ 14 C)‐glycine‐2‐ 3 H (IX) by alkaline hydrolysis. The specific activities of the compound were respectively 12.64 μCi ( 3 H)/μmole and 1.71 μCi ( 14 C)/μmole.
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