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

Author(s)

Campo, Vanessa L. ; Ivanova, Irina M. ; Carvalho, Ivone ; Lopes, Carla D. ; Carneiro, Zumira A. ; Saalbach, Gerhard ; Schenkman, Sergio ; da Silva, Joao Santana ; Nepogodiev, Sergey A. ; Field, Robert A.

• Document type: Journal article
• Source: Tetrahedron; v. 71, n. 39, p. 10-pg., 2015-09-30.

Abstract

Reaction of 2-(2-(2-azidoethoxy)ethoxy)ethyl 6-O-(prop-2-ynyl)-beta-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. (C) 2015 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license. (AU)

• FAPESP's process: 12/19390-0 - Development of mucin glycoconjugates with diagnostic and therapeutic applications in muscular dystrophies and cancer
• Grantee: Vanessa Leiria Campo
• Support Opportunities: Research Grants - Young Investigators Grants