Unique tetrameric and hexameric mannoside clusters prepared by click chemistry

Hussein Al-Mughaid; Raed M Al-Zoubi; Nawal K Paul; T Bruce Grindley

doi:10.1016/j.carres.2015.07.014

Unique tetrameric and hexameric mannoside clusters prepared by click chemistry

Carbohydr Res. 2015 Nov 19:417:27-33. doi: 10.1016/j.carres.2015.07.014. Epub 2015 Jul 30.

Authors

Hussein Al-Mughaid¹, Raed M Al-Zoubi², Nawal K Paul³, T Bruce Grindley³

Affiliations

¹ Department of Chemistry, Dalhousie University, Halifax, NS B3H 4J3, Canada; Department of Chemistry, Jordan University of Science and Technology, PO Box 3030, Irbid 22110, Jordan. Electronic address: al-mughaid@just.edu.jo.
² Department of Chemistry, Jordan University of Science and Technology, PO Box 3030, Irbid 22110, Jordan.
³ Department of Chemistry, Dalhousie University, Halifax, NS B3H 4J3, Canada.

PMID: 26398914
DOI: 10.1016/j.carres.2015.07.014

Abstract

The synthesis of novel tetrameric and hexameric mannoside clusters bearing 1,2,3-trizole linkages via Cu(I)-catalyzed azide-alkyne cycloaddition reaction ("click chemistry") is described. An attractive feature of these multiarmed mannoside clusters as potential inhibitors of uropathogenic Escherichia coli is the use of an aglycone whose length is designed to fit in the tyrosine gate. The acetylated mannosides were deprotected and the corresponding de-O-acetylated mannosides were found to exhibit good water solubility.

Keywords: Click chemistry; Trizoles; UTIs; α-d-Mannosides.

Publication types

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

MeSH terms

Alkynes / chemistry
Anti-Bacterial Agents / chemical synthesis*
Azides / chemistry
Carbohydrate Conformation
Catalysis
Click Chemistry / methods*
Copper / chemistry*
Cycloaddition Reaction
Mannosides / chemical synthesis*
Solubility
Triazoles / chemistry*
Water

Substances

Alkynes
Anti-Bacterial Agents
Azides
Mannosides
Triazoles
Water
Copper