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

Michieletti, M. and Bracci, A. and Compostella, F. and De Libero, G. and Mori, L. and Fallarini, S. and Lombardi, G. and Panza, L.. (2008) Synthesis of alpha-galactosyl ceramide (KRN7000) and analogues there of via a common precursor and their preliminary biological assessment. The journal of organic chemistry, Vol. 73, H. 22. pp. 9192-9195.

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Official URL: http://edoc.unibas.ch/dok/A6007165

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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.
Faculties and Departments:03 Faculty of Medicine > Departement Biomedizin > Department of Biomedicine, University Hospital Basel > Experimental Immunology (De Libero)
UniBasel Contributors:De Libero, Gennaro
Item Type:Article, refereed
Article Subtype:Research Article
Bibsysno:Link to catalogue
Publisher:American Chemical Society
ISSN:0022-3263
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:08 Nov 2012 16:22
Deposited On:08 Nov 2012 16:15

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