Synthesis of alpha-galactosyl ceramide (KRN7000) and analogues thereof via a common precursor and their preliminary biological assessment.
J Org Chem
; 73(22): 9192-5, 2008 Nov 21.
Article
en En
| MEDLINE
| ID: mdl-18956839
ABSTRACT
A new practical synthesis of alpha-GalCer and of its analogues is presented, opening the chance to easily modify the sphingosine chain. The common precursor is a disaccharide, obtained by coupling tetra-O-benzyl-D-galactose with allyl 2,3-O-isopropylidene-D-lyxofuranoside. Introduction of alkyl chains via Wittig reaction (for alpha-GalCer and OCH) or via Williamson reaction (for oxa analogues) followed by standard synthetic steps allows one to efficiently obtain such compounds. The analogues are able to activate iNKT cells when presented by CD1d expressing cells.
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1
Banco de datos:
MEDLINE
Asunto principal:
Galactosilceramidas
Idioma:
En
Año:
2008
Tipo del documento:
Article