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Synthese De La N‐acetylmuramyl (OXO‐ 14 C‐propyl)‐L‐alanyl‐D‐isoglutamine (MDP‐ 14 C)
Author(s) -
Pichat L.,
Tostain J.,
Lefrancier P.,
Sina P.,
Lederer E.
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.2580170117
Subject(s) - chemistry , hydrogenolysis , yield (engineering) , propionate , hydrochloride , sodium hydride , stereochemistry , acetic acid , reagent , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy
SYNTHESIS OF N‐ACETYLMURAMYL ( 14 C‐OXOPROPYL)‐L‐ALANYL‐D‐ ISOGLUTAMINE ( 14 C ‐ MDP) Condensation of (1‐ 14 C) DL‐2‐bromopropionic acid with benzyl 2‐acetamido‐4,6‐0‐benzylidene‐2‐deoxy‐β‐D‐glucopyranoside 7 in presence of sodium hydride gave 50 % of crystalline compound 3, having the correct stereochemistry of natural muramic acid. The latter, in presence of Woodward's reagent, reacted with L‐alanyl‐D‐isoglutamine benzyl ester hydrochloride, leading to compound 4. Removal of benzylidene and benzyl groups by successive acetic acid exposure and hydrogenolysis gave rise to 2‐acetamido‐2‐deoxy‐3‐0 (2‐D‐( 14 CO) propionyl‐L‐alanyl‐D‐isoglutamine)‐D‐glucopyranose ( 14 C‐MDP) Specific activity : 42 mCi/mMole in a 10 % overall yield based on sodium (1‐ 14 C) propionate.