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

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...

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Autores principales: Gloe, Tobias-Elias, Stamer, Insa, Hojnik, Cornelia, Wrodnigg, Tanja M, Lindhorst, Thisbe K
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4505182/
https://www.ncbi.nlm.nih.gov/pubmed/26199665
http://dx.doi.org/10.3762/bjoc.11.123
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author Gloe, Tobias-Elias
Stamer, Insa
Hojnik, Cornelia
Wrodnigg, Tanja M
Lindhorst, Thisbe K
author_facet Gloe, Tobias-Elias
Stamer, Insa
Hojnik, Cornelia
Wrodnigg, Tanja M
Lindhorst, Thisbe K
author_sort Gloe, Tobias-Elias
collection PubMed
description 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 within the carbohydrate binding site of the type 1-fimbrial lectin FimH.
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spelling pubmed-45051822015-07-21 Are D-manno-configured Amadori products ligands of the bacterial lectin FimH? Gloe, Tobias-Elias Stamer, Insa Hojnik, Cornelia Wrodnigg, Tanja M Lindhorst, Thisbe K Beilstein J Org Chem Full Research Paper 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 within the carbohydrate binding site of the type 1-fimbrial lectin FimH. Beilstein-Institut 2015-06-30 /pmc/articles/PMC4505182/ /pubmed/26199665 http://dx.doi.org/10.3762/bjoc.11.123 Text en Copyright © 2015, Gloe et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Gloe, Tobias-Elias
Stamer, Insa
Hojnik, Cornelia
Wrodnigg, Tanja M
Lindhorst, Thisbe K
Are D-manno-configured Amadori products ligands of the bacterial lectin FimH?
title Are D-manno-configured Amadori products ligands of the bacterial lectin FimH?
title_full Are D-manno-configured Amadori products ligands of the bacterial lectin FimH?
title_fullStr Are D-manno-configured Amadori products ligands of the bacterial lectin FimH?
title_full_unstemmed Are D-manno-configured Amadori products ligands of the bacterial lectin FimH?
title_short Are D-manno-configured Amadori products ligands of the bacterial lectin FimH?
title_sort are d-manno-configured amadori products ligands of the bacterial lectin fimh?
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4505182/
https://www.ncbi.nlm.nih.gov/pubmed/26199665
http://dx.doi.org/10.3762/bjoc.11.123
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