Solvent effect on the isomeric equilibrium of carbohydrates: the superior ability of 2,2,2-trifluoroethanol for intramolecular hydrogen bond stabilization

A Molinaro; C De Castro; R Lanzetta; E Manzo; M Parrilli

doi:10.1021/ja016471i

Solvent effect on the isomeric equilibrium of carbohydrates: the superior ability of 2,2,2-trifluoroethanol for intramolecular hydrogen bond stabilization

J Am Chem Soc. 2001 Dec 19;123(50):12605-10. doi: 10.1021/ja016471i.

Authors

A Molinaro¹, C De Castro, R Lanzetta, E Manzo, M Parrilli

Affiliation

¹ Department of Organic Chemistry and Biochemistry, University Federico II, Complesso Universitario Monte S'Angelo, Via Cintia 4, 80126 Napoli, Italy. [email protected]

PMID: 11741425
DOI: 10.1021/ja016471i

Abstract

The higher aptitude of 2,2,2-trifluoroethanol for intramolecular hydrogen bond stabilization in carbohydrates is suggested. This belief, arising from the analysis by 1H NMR spectroscopy of the solvent effect of D2O, DMSO-d6, and 2,2,2-trifluoroethanol-d3 on the isomeric equilibrium of caryophyllose, was also confirmed by shifting of the conformational equilibria of beta-ribopyranose and of its methyl glycoside.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbohydrate Conformation
Deuterium Oxide / chemistry
Dimethyl Sulfoxide / chemistry
Hydrogen Bonding
Kinetics
Monosaccharides / chemistry*
Nuclear Magnetic Resonance, Biomolecular
Polysaccharides / chemistry
Ribose / chemistry*
Solvents
Trifluoroethanol / chemistry*

Substances

Monosaccharides
Polysaccharides
Solvents
caryophyllan
methyl -caryophylloside
Ribose
Trifluoroethanol
Deuterium Oxide
Dimethyl Sulfoxide