Abstract
Abstract The synthesis of the d-manno analogue of muramic acid, 2-amino-3-O-(d-1-carboxyethyl)-2-deoxy-d-mannose, was started from methyl 2-acetamido-4,6-O-benzylidene-3-O-(methylsulfonyl)-α-d-altropyranoside, which was transformed into methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-d-mannopyranoside. After condensation with l-2-chloropropionic acid and removal of the protective benzylidene group, hydrolysis gave the title compound in amorphous form. The N-acetyl derivative, also amorphous, could be easily identified from the d-gluco and d-galacto analogues by gas-liquid chromatography of the per(trimethylsilyl) derivatives of the N-acetyl derivatives. Separation of the d-gluco and d-manno analogues was also accomplished on the per-(trimethylsilyl) derivatives of the methyl N-acetyl-α-d-glycoside, methyl esters, and amides.
Highlights
After condensation with L-Z-chloropropionic acid and removal of the protective benzylidene group, hydrolysis gave the title compound in amorphous form
Its polysaccharide moiety consists of a repeating unit containing 2-acetamido-2-deoxy-D-glucopyranosyl and 2-acetamido-3-O-(o-l-carboxyethyl)-2-deoxy-u-glucopyranosyl (N-acetylmuramic acid) residues [3]
In order to establish definitely the structure, its synthesis was accomplished, and the synthetic compound was compared to the synthetic D-gluco and u-galacto [4] analogues and to the natural u-manno analogue
Summary
The synthesis of the D-manno analogue of muramic acid, 2-amino-3-0+-lcarboxyethyl) -2 - deoxy-D -mannose, was started from methyl 2-acetamido-4,6-0-benzylidene-3-0-. H. Gross from the National Science Foundation (Grant GP-12222). Gross from the National Science Foundation (Grant GP-12222) This is Publication LXX111 of the series on amino sugars and 551 of the Robert W. In the preceding paper [2], the isolation, from the glycall part of the peptidoglycan of Jlicrococcus lysodeikficus cell wall, of a component similar to, but not identical with muramic acid, has been described. Amil~o-3-0-(o-l-carbox~~eth~l)-2-deoxy-r~-mar~nose was ascribed to this new acidic carbohydrate component of the bacterial cell wall. In order to establish definitely the structure, its synthesis was accomplished, and the synthetic compound was compared to the synthetic D-gluco and u-galacto [4] analogues and to the natural u-manno analogue
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