A Highly Sensitive Method to Identify the D, L-Configurations of Monosaccharides Based on (-)-TBMB Carboxylic Acid and HPLC

1 October 1994

journal article
research article
Published by Taylor & Francis in Journal of Carbohydrate Chemistry

Vol. 13 (7) , 1003-1008
https://doi.org/10.1080/07328309408011842

Abstract

D, L-Isomers of monosaccharides were coupled with a fluorescent chiral derivatizing agent, (-)-2-tert-butyl-2-methyl-1,3-benzodioxole-4-carboxylic acid [(-)-TBMB carboxylic acid], to afford a pair of diastereoisomers. The two were well separated with HPLC (reverse phase conditions; ODS, CH₃CN:H₂O:isoPrOH) within 60 min and could be detected by fluorescence of the TBMB group at the few picomolar level.

Keywords

This publication has 9 references indexed in Scilit:

Assignment of absolute configuration of sugars by g.l.c. of their acetylated glycosides formed from chiral alcohols
Published by Elsevier ,2001
Determination of the absolute configuration of monosaccharides using (+) or (−) 2-tert-butyl-2-methyl-1,3-benzodioxole-4-carboxylic acid and high-resolution 1H-n.m.r. spectroscopy
Carbohydrate Research, 1991
Crystal Structure of N-[(+)-2-t-Butyl-2-methyl-1,3-benzodioxole-4-carbonyl]-l-phenylalanine Methyl Ester
Analytical Sciences, 1991
Synthesis of (S)-(+)-2-tert-butyl-2-methyl-1,3-benzodioxole-4-carboxylic acid: A new type chiral derivation reagent for amines and alcohols
Tetrahedron Letters, 1989
Enantioselective gas chromatography with modified cyclomalto-oligosaccharides as chiral stationary phases
Carbohydrate Research, 1989
A method to identify the absolute configuration of rhamnose, lyxose, and 2,6-dideoxy sugars, cymarose, oleandrose, diginose, and digitoxose, using a chiral high-performance liquid chromatography(HPLC) column.
CHEMICAL & PHARMACEUTICAL BULLETIN, 1989
Gas-liquid chromatographic separation of aldose enantiomers as trimethylsilyl ethers of methyl 2-(polyhydroxyalkyl)-thiazolidine-4(R)-carboxylates.
CHEMICAL & PHARMACEUTICAL BULLETIN, 1987
Determination of the absolute configuration of monosaccharides in complex carbohydrates by capillary g.l.c.
Carbohydrate Research, 1979
Determination of the d and l configuration of neutral monosaccharides by high-resolution capillary g.l.c.
Carbohydrate Research, 1978