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Muramyl Peptides, 1 Stereochemically Pure Derivatives of Muramic and Isomuramic Acids
Author(s) -
Gross Paul H.,
Rimpler Manfred
Publication year - 1986
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198619860104
Subject(s) - chemistry , muramic acid , enantiomer , yield (engineering) , stereoselectivity , stereospecificity , stereochemistry , ether , alanine , amino acid , organic chemistry , catalysis , biochemistry , materials science , peptidoglycan , metallurgy , enzyme
An improved, large‐scale preparation is described, leading from 2‐acetamido‐2‐deoxy‐ D ‐glucose to benzyl 2‐acetamido‐4,6‐ O ‐benzylidene‐3‐ O ‐[(R)‐1‐carboxyethyl]‐2‐deoxy‐α‐ D ‐glucopyranoside (α‐Benzyl N ‐acetyl‐4,6‐ O ‐benzylidenemuramic acid. 5r ) and its ( S )‐isomer (α‐Benzyl N ‐acetyl‐4,6‐ O ‐benzylideneisomuramic acid, 5s ) via chromatographic separation of their methyl esters ( 4r and 4s ). The high yield and complete separation of 4r and 4s allow a reliable assessment of the low stereoselectivity of the lactyl ether synthesis step from racemic 2‐chloropropionic acid. Similarly, syntheses employing pure enantiomers of 2‐chloropropionic acid were disclosed as not completely stereospecific. Coupling products with L ‐ and D ‐alanine esters were prepared for both 5r and 5s .