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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.

Campo VL, Ivanova IM, Carvalho I, Lopes CD, Carneiro ZA, Saalbach G, Schenkman S, da Silva JS, Nepogodiev SA, Field RA - Tetrahedron (2015)

Bottom Line: 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 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.

View Article: PubMed Central - PubMed

Affiliation: Faculdade de Ciências Farmacêuticas de Ribeirão Preto, USP, Av. Café S/N, CEP 14040-903, Ribeirão Preto, SP, Brazil.

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.

No MeSH data available.


Spontaneous cyclisation and oligomerisation of monomer 7 leading to a mixture of compounds incorporating both 1,4-linked and 1,5-linked 1,2,3-triazole residues.
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sch3: Spontaneous cyclisation and oligomerisation of monomer 7 leading to a mixture of compounds incorporating both 1,4-linked and 1,5-linked 1,2,3-triazole residues.

Mentions: Given the noted spontaneous but slow 1,3-dipolar cycloaddition of monomer 7 on standing at room temperature (vide supra), the reactivity of 7 at 1 M concentration in DMF at 110 °C (under microwave irradiation; Method C) and at room temperature (Method D) were compared (Scheme 3). Reaction using Method C was complete after 30 min, while Method D gave approximately 10% conversion of monomer 7 after two weeks. TLC analysis showed even more complex multiple product mixtures than the Cu(I)-catalysed reaction (Fig. 2, TLC lanes C and D) due to the expected formation of mixed isomeric 1,4- and 1,5-linked triazoles.


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

Campo VL, Ivanova IM, Carvalho I, Lopes CD, Carneiro ZA, Saalbach G, Schenkman S, da Silva JS, Nepogodiev SA, Field RA - Tetrahedron (2015)

Spontaneous cyclisation and oligomerisation of monomer 7 leading to a mixture of compounds incorporating both 1,4-linked and 1,5-linked 1,2,3-triazole residues.
© Copyright Policy - CC BY
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4542550&req=5

sch3: Spontaneous cyclisation and oligomerisation of monomer 7 leading to a mixture of compounds incorporating both 1,4-linked and 1,5-linked 1,2,3-triazole residues.
Mentions: Given the noted spontaneous but slow 1,3-dipolar cycloaddition of monomer 7 on standing at room temperature (vide supra), the reactivity of 7 at 1 M concentration in DMF at 110 °C (under microwave irradiation; Method C) and at room temperature (Method D) were compared (Scheme 3). Reaction using Method C was complete after 30 min, while Method D gave approximately 10% conversion of monomer 7 after two weeks. TLC analysis showed even more complex multiple product mixtures than the Cu(I)-catalysed reaction (Fig. 2, TLC lanes C and D) due to the expected formation of mixed isomeric 1,4- and 1,5-linked triazoles.

Bottom Line: 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 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.

View Article: PubMed Central - PubMed

Affiliation: Faculdade de Ciências Farmacêuticas de Ribeirão Preto, USP, Av. Café S/N, CEP 14040-903, Ribeirão Preto, SP, Brazil.

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.

No MeSH data available.