An easy stereospecific synthesis of 1-amino-2,5-anhydro-1-deoxy-D-mannitol and arylamino derivatives

S Claustre; F Bringaud; L Azéma; R Baron; J Périé; M Willson

doi:10.1016/s0008-6215(99)00040-3

An easy stereospecific synthesis of 1-amino-2,5-anhydro-1-deoxy-D-mannitol and arylamino derivatives

Carbohydr Res. 1999 Feb 28;315(3-4):339-44. doi: 10.1016/s0008-6215(99)00040-3.

Authors

S Claustre¹, F Bringaud, L Azéma, R Baron, J Périé, M Willson

Affiliation

¹ UMR CNRS 5623, Université Paul Sabatier, Toulouse, France.

PMID: 10399304
DOI: 10.1016/s0008-6215(99)00040-3

Abstract

1-Amino-2,5-anhydro-1-deoxy-D-mannitol and a series of arylamino derivatives were prepared by nitrous acid deamination of 2-amino-2-deoxy-D-glucose and subsequent reductive amination of the resulting 2,5-anhydro-D-mannose. Some of these compounds showed an enhanced affinity for the hexose transporter of Trypanosoma brucei as compared to D-fructose.

Publication types

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

MeSH terms

Animals
Carbohydrate Sequence
Kinetics
Mannitol / analogs & derivatives*
Mannitol / chemical synthesis
Molecular Sequence Data
Monosaccharide Transport Proteins / metabolism
Trypanosoma brucei brucei / chemistry

Substances

1-amino-2,5-anhydro-1-deoxymannitol
Monosaccharide Transport Proteins
Mannitol