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Chemical and enzymatic synthesis of fructose analogues as probes for import studies by the hexose transporter in parasites.

Abstract：

:Various D-fructose analogues modified at C-1 or C-6 positions were synthesized from D-glucose by taking advantage of the Amadori rearrangement or using the aldol condensation between dihydroxyacetone phosphate and appropriate aldehyde catalyzed by fructose 1,6-diphosphate aldolase from rabbit muscle. The affinities of the analogues for the glucose transporter expressed in the mammalian form of Trypanosoma brucei were determined by inhibition of radiolabelled 2-deoxy-D-glucose (2-DOG) transport using zero-trans kinetic analysis. Interestingly, the analogues bearing an aromatic group (i.e. a fluorescence marker) at C-1 or C-6 positions present comparable apparent affinities to D-fructose for the transporter. This result could find applications for hexose transport studies and also provides criteria for the design of glucose import inhibitors.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Azéma L,Bringaud F,Blonski C,Périé J

doi

10.1016/s0968-0896(00)00018-3

subject

Has Abstract

pub_date

2000-04-01 00:00:00

pages

717-22

issue

4

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(00)00018-3

journal_volume

8

pub_type

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