A method for determination of the absolute configuration of chiral glycerol residues in natural products using TEMPO oxidation and characterization of the glyceric acids formed

Analytical Biochemistry
T Rundlöf, G Widmalm

Abstract

A method has been developed for determination of the absolute configuration of glycerol residues in natural products. It is required that the glycerol moiety contain a primary nonsubstituted hydroxymethyl group or that such a group can be obtained by modification without racemization. The method employs TEMPO oxidation of the primary hydroxyl group, hydrolysis, butanolysis with chiral 2-butanol, and acetylation. The acetylated (+)-2-butyl esters of the glyceric acid formed by oxidation are analyzed by gas-liquid chromatography. The esterification can also be performed with other chiral alcohols, e.g., (-)-2-octanol. The method is general and applicable to both primary and secondary substituted glycerols. It has recently been used for determination of the chiral glycerol-1-phosphate residue of the Escherichia coli O28 O-antigen, and now we report the absolute configurations of the glycerol moieties in Streptococcus pneumoniae type 18A and Streptococcus agalactaie type III. All studied glycerol residues were found to have the D-configuration.

Citations

Jan 29, 2000·European Journal of Biochemistry·A V PerepelovY A Knirel
Nov 13, 2004·Biochimica Et Biophysica Acta·Mariola PaściakAndrzej Gamian
Feb 1, 2005·FEMS Immunology and Medical Microbiology·Krystyna ZychZygmunt Sidorczyk
Feb 5, 2002·Biochimica Et Biophysica Acta·Mariola PaściakAndrzej Gamian
Jun 21, 2006·Carbohydrate Research·Andrei V PerepelovLei Wang

❮ Previous
Next ❯

Related Concepts

Related Feeds

Bacterial Pneumonia

Bacterial pneumonia is a prevalent and costly infection that is a significant cause of morbidity and mortality in patients of all ages. Here is the latest research.

Bacterial Pneumonia (ASM)

Bacterial pneumonia is a prevalent and costly infection that is a significant cause of morbidity and mortality in patients of all ages. Here is the latest research.