An easy stereospecific synthesis of 1-amino-2,5-anhydro-1-deoxy-D-mannitol and arylamino derivatives.
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.
Claustre
S
S
UMR CNRS 5623, Université Paul Sabatier, Toulouse, France.
Bringaud
F
F
Azéma
L
L
Baron
R
R
Périé
J
J
Willson
M
M
D000818:Animals; D002240:Carbohydrate Sequence; D007700:Kinetics; D008353:Mannitol / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D008969:Molecular Sequence Data; D009004:Monosaccharide Transport Proteins / Q000378:metabolism; D014346:Trypanosoma brucei brucei / Q000737:chemistry
C120873:1-amino-2,5-anhydro-1-deoxymannitol; D009004:Monosaccharide Transport Proteins; D008353:Mannitol