Synthesis of α-galactosyl ceramide (KRN7000) and analogues thereof via a common precursor and their preliminary biological assessment

Mario Michieletti, Antonio Bracci, Federica Compostella, Gennaro De Libero, Lucia Mori, Silvia Fallarini, Grazia Lombardi, Luigi Panza

Risultato della ricerca: Contributo su rivistaArticolo in rivistapeer review

Abstract

(Chemical Equation Presented) A new practical synthesis of α-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 α-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.

Lingua originaleInglese
pagine (da-a)9192-9195
Numero di pagine4
RivistaJournal of Organic Chemistry
Volume73
Numero di pubblicazione22
DOI
Stato di pubblicazionePubblicato - 21 nov 2008

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