Synthesis of novel triazole-derived glycopeptides as analogs of α-dystroglycan mucins.
Glycopeptide
Mucin
Synthesis
Triazole
α-Dystroglycan
β-1,4-Galactosyltransferase
Journal
Carbohydrate research
ISSN: 1873-426X
Titre abrégé: Carbohydr Res
Pays: Netherlands
ID NLM: 0043535
Informations de publication
Date de publication:
15 Jan 2019
15 Jan 2019
Historique:
received:
26
09
2018
revised:
05
11
2018
accepted:
05
11
2018
pubmed:
20
11
2018
medline:
5
6
2019
entrez:
20
11
2018
Statut:
ppublish
Résumé
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
Identifiants
pubmed: 30453095
pii: S0008-6215(18)30559-7
doi: 10.1016/j.carres.2018.11.004
pii:
doi:
Substances chimiques
Glycopeptides
0
Mucins
0
Triazoles
0
Dystroglycans
146888-27-9
N-Acetyllactosamine Synthase
EC 2.4.1.90
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
23-32Informations de copyright
Copyright © 2018 Elsevier Ltd. All rights reserved.