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

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

doi:10.1016/j.tet.2015.04.085

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

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

Research output: Contribution to journal › Article › peer-review

30 Citations (Scopus)

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.

Original language	English
Article number	26688
Pages (from-to)	7344-7353
Number of pages	10
Journal	Tetrahedron
Volume	71
Issue number	39
Early online date	6 May 2015
DOIs	https://doi.org/10.1016/j.tet.2015.04.085
Publication status	Published - 17 Aug 2015

Keywords

Click chemistry
Macrophage invasion
Pseudo-glycomacrocycles
Triazole-linked oligomers
Trypanosoma cruzi

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10.1016/j.tet.2015.04.085Licence: CC BY

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Campo, V. L., Ivanova, I. M., Carvalho, I., Lopes, C. D., Carneiro, Z. A., Saalbach, G., Schenkman, S., da Silva, J. S., Nepogodiev, S. A., & Field, R. A. (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), 7344-7353. Article 26688. https://doi.org/10.1016/j.tet.2015.04.085

@article{d51a8f4da9594eb1aa7b6541a7d17b30,

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

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.",

keywords = "Click chemistry, Macrophage invasion, Pseudo-glycomacrocycles, Triazole-linked oligomers, Trypanosoma cruzi",

author = "Campo, \{Vanessa L.\} and Ivanova, \{Irina M.\} and Ivone Carvalho and Lopes, \{Carla D.\} and Carneiro, \{Zumira A.\} and Gerhard Saalbach and Sergio Schenkman and \{da Silva\}, \{Jo{\~a}o Santana\} and Nepogodiev, \{Sergey A.\} and Field, \{Robert A.\}",

year = "2015",

month = aug,

day = "17",

doi = "10.1016/j.tet.2015.04.085",

language = "English",

volume = "71",

pages = "7344--7353",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "39",

}

Campo, VL, Ivanova, IM, Carvalho, I, Lopes, CD, Carneiro, ZA, Saalbach, G, Schenkman, S, da Silva, JS, Nepogodiev, SA & Field, RA 2015, 'Click chemistry oligomerisation of azido-alkyne-functionalised galactose accesses triazole-linked linear oligomers and macrocycles that inhibit Trypanosoma cruzi macrophage invasion', Tetrahedron, vol. 71, no. 39, 26688, pp. 7344-7353. https://doi.org/10.1016/j.tet.2015.04.085

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 et al.
In: Tetrahedron, Vol. 71, No. 39, 26688, 17.08.2015, p. 7344-7353.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Click chemistry oligomerisation of azido-alkyne-functionalised galactose accesses triazole-linked linear oligomers and macrocycles that inhibit Trypanosoma cruzi macrophage invasion

AU - Campo, Vanessa L.

AU - Ivanova, Irina M.

AU - Carvalho, Ivone

AU - Lopes, Carla D.

AU - Carneiro, Zumira A.

AU - Saalbach, Gerhard

AU - Schenkman, Sergio

AU - da Silva, João Santana

AU - Nepogodiev, Sergey A.

AU - Field, Robert A.

PY - 2015/8/17

Y1 - 2015/8/17

N2 - 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.

AB - 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.

KW - Click chemistry

KW - Macrophage invasion

KW - Pseudo-glycomacrocycles

KW - Triazole-linked oligomers

KW - Trypanosoma cruzi

UR - https://www.scopus.com/pages/publications/84939254785

U2 - 10.1016/j.tet.2015.04.085

DO - 10.1016/j.tet.2015.04.085

M3 - Article

AN - SCOPUS:84939254785

SN - 0040-4020

VL - 71

SP - 7344

EP - 7353

JO - Tetrahedron

JF - Tetrahedron

IS - 39

M1 - 26688

ER -

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

Abstract

Keywords

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