Journal of the American Chemical Society p. 1114 - 1120 (1993)
Update date:2022-08-04
Topics:
Severn, Wayne B.
Richards, James C.
A general strategy for the stereochemical analysis of 1-carboxyethyl sugar ethers is introduced in which the chirality of the lactyl group is related to that of the sugar moiety in a conformationally rigid lactone derivative.With the aid of molecular modeling, the stereochemistry is determined through the use of NOE measurements.This procedure was evaluated using synthetic diastereomeric samples of (R)- and (S)-methyl 3-O-(1-carboxyethyl)-α-L-rhamnopyranoside, and it was successfully applied to the stereochemical analysis of N-acetylmuramic acid.The generality of this approach is illustrated here with a 4-O-substituted 1-carboxyethyl sugar ether.It was found that the lactyl group of 4-O-(1-carboxyethyl)-D-mannopyranose, which was obtained from the capsular polysaccharide of Rhodococcus equi serotype 3, has the (S)-configuration.
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