| Texto completo | |
| Autor(es): |
Figueredo, Andreza S.
[1]
;
Zamoner, Luis O. B.
[1]
;
Rejzek, Martin
[2]
;
Field, Robert A.
[2]
;
Carvalho, Ivone
[1]
Número total de Autores: 5
|
| Afiliação do(s) autor(es): | [1] Univ Sao Paulo, Sch Pharmaceut Sci Ribeirao Preto, Ave Cafe S-N, BR-14040903 Ribeirao Preto - Brazil
[2] John Innes Ctr, Dept Biol Chem, Norwich Res Pk, Norwich NR4 7UH, Norfolk - England
Número total de Afiliações: 2
|
| Tipo de documento: | Artigo Científico |
| Fonte: | Tetrahedron Letters; v. 59, n. 50, p. 4405-4409, DEC 12 2018. |
| Citações Web of Science: | 1 |
| Resumo | |
Multivalent carbohydrates, or glycoclusters, are useful tools to study glycan-lectin and glycan-enzyme recognition processes and have wide potential therapeutic applicability. Herein, we report the synthesis of novel glycoclusters presenting glucopyranose units in alternate arrangements by coupling through the C-1, C-2, C-3 or C-6 sugar positions and using tetra- and hexa-valent scaffolds for multivalent display. Coupling the appropriate azide-functionalised D-glucopyranose units with alkynylated penta- or dipenta-erythritol central cores was accomplished via copper-catalysed azide-alkyne cycloaddition (CuAAC), yielding a panel of eight tetra- and hexa-valent glycoclusters in good yields (52-83%). This click chemistry strategy was extended to the preparation of four heteroglycoclusters using a tris(hydroxymethyl)-aminomethane (TRIS) central scaffold. One unit of either the conventional 1-deoxy-D-nojirymicin iminosugar or its' C-5 epimeric L-gulo isomer, were incorporated along with three D-glucopyranose units linked through either C-1 or C-6. (C) 2018 Elsevier Ltd. All rights reserved. (AU) | |
| Processo FAPESP: | 13/27038-8 - Síntese e avaliação biológica de "glycoclusters" com potencial antiparasitário, antimicrobiano e antitumoral. |
| Beneficiário: | Andreza da Silva Figueredo |
| Modalidade de apoio: | Bolsas no Brasil - Doutorado |