Click chemistry oligomerisation of azido-alkyne-functionalised galactose accesses triazole-linked linear oligomers and macrocycles that inhibit Trypanosoma cruzi macrophage invasion

Campo, Vanessa L., Ivanova, Irina M., Carvalho, Ivone, Lopes, Carla D., Carneiro, Zumira A., Saalbach, Gerhard, Schenkman, Sergio, da Silva, João Santana, Nepogodiev, Sergey A. and Field, Robert A. ORCID: https://orcid.org/0000-0001-8574-0275 (2015) Click chemistry oligomerisation of azido-alkyne-functionalised galactose accesses triazole-linked linear oligomers and macrocycles that inhibit Trypanosoma cruzi macrophage invasion. Tetrahedron, 71 (39). pp. 7344-7353. ISSN 0040-4020

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Abstract

Abstract Reaction of 2-(2-(2-azidoethoxy)ethoxy)ethyl 6-O-(prop-2-ynyl)-β-d-galactopyranoside (7) under CuAAC conditions gives rise to mixed cyclic and linear triazole-linked oligomers, with individual compounds up to d.p. 5 isolable, along with mixed larger oligomers. The linear compounds resolve en bloc from the cyclic materials by RP HPLC, but are separable by gel permeation chromatography. The triazole-linked oligomers - pseudo-galactooligomers - were demonstrated to be acceptor substrates for the multi-copy cell surface trans-sialidase of the human parasite Trypanosoma cruzi. In addition, these multivalent TcTS ligands were able to block macrophage invasion by T. cruzi.

Item Type:	Article
Uncontrolled Keywords:	click chemistry,macrophage invasion,pseudo-glycomacrocycles,triazole-linked oligomers,trypanosoma cruzi,biochemistry,drug discovery,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1300/1303
Faculty \ School:	Faculty of Science > School of Chemistry, Pharmacy and Pharmacology
Related URLs:	http://www.scopus.com/inward/record.url?...
Depositing User:	LivePure Connector
Date Deposited:	04 Sep 2024 13:35
Last Modified:	25 Sep 2024 18:06
URI:	https://ueaeprints.uea.ac.uk/id/eprint/96537
DOI:	10.1016/j.tet.2015.04.085

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