Synthesis of novel triazole-derived glycopeptides as analogs of α-dystroglycan mucins.
Autor: | Marchiori MF; Faculty of Pharmaceutical Sciences of Ribeirão Preto - USP, Av. do Café S/N, CEP 14040-903, Ribeirão Preto, SP, Brazil., Iossi GP; Faculty of Pharmaceutical Sciences of Ribeirão Preto - USP, Av. do Café S/N, CEP 14040-903, Ribeirão Preto, SP, Brazil., Bortot LO; Faculty of Pharmaceutical Sciences of Ribeirão Preto - USP, Av. do Café S/N, CEP 14040-903, Ribeirão Preto, SP, Brazil., Dias-Baruffi M; Faculty of Pharmaceutical Sciences of Ribeirão Preto - USP, Av. do Café S/N, CEP 14040-903, Ribeirão Preto, SP, Brazil., Campo VL; Faculty of Pharmaceutical Sciences of Ribeirão Preto - USP, Av. do Café S/N, CEP 14040-903, Ribeirão Preto, SP, Brazil; Barão de Mauá University Centre, 423 Ramos de Azevedo Street, Jardim Paulista, CEP 14090-180, Ribeirão Preto, SP, Brazil. Electronic address: vlcampo@fcfrp.usp.br. |
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Jazyk: | angličtina |
Zdroj: | Carbohydrate research [Carbohydr Res] 2019 Jan 15; Vol. 472, pp. 23-32. Date of Electronic Publication: 2018 Nov 11. |
DOI: | 10.1016/j.carres.2018.11.004 |
Abstrakt: | α-Dystroglycan (α-DG) mucins are essential for maintenance of the structural and functional stability of the muscle fiber and, when hypoglycosylated, they are directly involved in pathological processes such as dystroglycanopathies. Thus, this work reports the synthesis of the novel 1,2,3-triazole-derived glycosyl amino acids αGlcNAc-1-O-triazol-2Manα-ThrOH (1) and Gal-β1,4-αGlcNAc-1-O-triazol-2Manα-ThrOH (2), followed by solid-phase assembly to get the corresponding glycopeptides NHAcThrVal[αGlcNAc-1-triazol-2Manα]ThrIleArgGlyOH (3) and NHAcThrVal[Gal-β1,4-αGlcNAc-1-triazol-2Manα]ThrIleArgGlyOH (4) as analogs of α-DG mucins. The glycosyl amino acids 1 (72%) and 2 (35%) were synthesized by Cu(I)-assisted 1,3-dipolar azide-alkyne cycloaddition reactions (CuAAC) between the azide-glycosyl amino acid αManN (Copyright © 2018 Elsevier Ltd. All rights reserved.) |
Databáze: | MEDLINE |
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