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Are D-manno-configured Amadori products ligands of the bacterial lectin FimH?

ABSTRACT: The Amadori rearrangement was employed for the synthesis of C-glycosyl-type D-mannoside analogues, namely 1-propargylamino- and 1-phenylamino-1-deoxy-?-D-manno-heptopyranose. They were investigated as ligands of type 1-fimbriated E. coli bacteria by means of molecular docking and bacterial adhesion studies. It turns out that Amadori rearrangement products have a limited activity as inhibitors of bacterial adhesion because the ?-C-glycosidically linked aglycone considerably hampers complexation within the carbohydrate binding site of the type 1-fimbrial lectin FimH.

SUBMITTER: Gloe TE

PROVIDER: S-EPMC4505182 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

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Are D-manno-configured Amadori products ligands of the bacterial lectin FimH?

Gloe Tobias-Elias TE Stamer Insa I Hojnik Cornelia C Wrodnigg Tanja M TM Lindhorst Thisbe K TK

Beilstein journal of organic chemistry 20150630

The Amadori rearrangement was employed for the synthesis of C-glycosyl-type D-mannoside analogues, namely 1-propargylamino- and 1-phenylamino-1-deoxy-α-D-manno-heptopyranose. They were investigated as ligands of type 1-fimbriated E. coli bacteria by means of molecular docking and bacterial adhesion studies. It turns out that Amadori rearrangement products have a limited activity as inhibitors of bacterial adhesion because the β-C-glycosidically linked aglycone considerably hampers complexation w ...[more]

PMID: 26199665

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