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Synthese De La N-acetylmuramyl (OXO-14C-propyl)-L-alanyl-D-isoglutamine (MDP-14C)

✍ Scribed by L. Pichat; J. Tostain; P. Lefrancier; P. Sina; E. Lederer

Publisher
John Wiley and Sons
Year
1980
Tongue
French
Weight
251 KB
Volume
17
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

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.

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