A versatile synthesis of αGalCer and its analogues exploiting a cyclic carbonate as phytosphingosine 3,4-diol protecting group.
Glycosphingolipids
Glycosylation
Phytosphingosine acceptor
α-Galactosylceramide analogues
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:
23
10
2018
revised:
06
11
2018
accepted:
06
11
2018
pubmed:
25
11
2018
medline:
5
6
2019
entrez:
25
11
2018
Statut:
ppublish
Résumé
A convenient synthetic strategy to αGalCer and some relevant analogues by using a handily protected phytosphingosine is reported here. The conversion of the phytosphingosine amino group to azide and the protection of 3,4-diol as cyclic carbonate group, cleavable in mild basic conditions but resistant to acidic treatment, afforded quickly an excellent glycosyl acceptor. Its glycosylation with a proper galactosyl donor, gave a versatile intermediate in high yield and excellent stereoselectivity. To demonstrate the potentiality of the intermediate, three immunologically relevant compounds were chosen as model targets: αGalCer, dansyl alpha-galactosylceramide and 7DW8-5. These products were easily obtained in few steps and high yields to validate the synthetic route.
Identifiants
pubmed: 30471510
pii: S0008-6215(18)30617-7
doi: 10.1016/j.carres.2018.11.005
pii:
doi:
Substances chimiques
Carbonates
0
Galactosylceramides
0
alpha-galactosylceramide
0
phytosphingosine
GIN46U9Q2Q
Sphingosine
NGZ37HRE42
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
50-57Informations de copyright
Copyright © 2018 Elsevier Ltd. All rights reserved.