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

ABSTRACT: Reaction of 2-(2-(2-azidoethoxy)ethoxy)ethyl 6-O-(prop-2-ynyl)-?-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.

SUBMITTER: Campo VL 

PROVIDER: S-EPMC4542550 | biostudies-literature | 2015 Sep

REPOSITORIES: biostudies-literature

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

Campo Vanessa L VL   Ivanova Irina M IM   Carvalho Ivone I   Lopes Carla D CD   Carneiro Zumira A ZA   Saalbach Gerhard G   Schenkman Sergio S   da Silva João Santana JS   Nepogodiev Sergey A SA   Field Robert A RA  

Tetrahedron 20150901 39

Reaction of 2-(2-(2-azidoethoxy)ethoxy)ethyl 6-<i>O</i>-(prop-2-ynyl)-β-d-galactopyranoside (<b>7</b>) 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 <i>en bloc</i> from the cyclic materials by RP HPLC, but are separable by gel permeation chromatography. The triazole-linked oligomers-<i>pseudo</i>-galactooligomers-were demonstrated to be accept  ...[more]

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