Synthesis and biological activity of alpha-galactosyl ceramide KRN7000 and galactosyl (alpha1-->2) galactosyl ceramide.

We herein report a faster and less cumbersome synthesis of the biologically attractive, alpha-galactosyl ceramide (alpha-GalCer), known as KRN7000, and its analogues. More importantly, the use of a silicon tethered intramolecular glycosylation reaction gave easy access to the diglycosyl ceramide Gal...

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Main Authors: Veerapen, N, Brigl, M, Garg, S, Cerundolo, V, Cox, L, Brenner, M, Besra, G
Format: Journal article
Language:English
Published: 2009
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author Veerapen, N
Brigl, M
Garg, S
Cerundolo, V
Cox, L
Brenner, M
Besra, G
author_facet Veerapen, N
Brigl, M
Garg, S
Cerundolo, V
Cox, L
Brenner, M
Besra, G
author_sort Veerapen, N
collection OXFORD
description We herein report a faster and less cumbersome synthesis of the biologically attractive, alpha-galactosyl ceramide (alpha-GalCer), known as KRN7000, and its analogues. More importantly, the use of a silicon tethered intramolecular glycosylation reaction gave easy access to the diglycosyl ceramide Gal(alpha1-->2)GalCer, which has been shown to require uptake and processing to the biologically active alpha-GalCer derivative.
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spelling oxford-uuid:446f1d9a-250f-45c6-b221-731836abcf962022-03-26T15:01:30ZSynthesis and biological activity of alpha-galactosyl ceramide KRN7000 and galactosyl (alpha1-->2) galactosyl ceramide.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:446f1d9a-250f-45c6-b221-731836abcf96EnglishSymplectic Elements at Oxford2009Veerapen, NBrigl, MGarg, SCerundolo, VCox, LBrenner, MBesra, GWe herein report a faster and less cumbersome synthesis of the biologically attractive, alpha-galactosyl ceramide (alpha-GalCer), known as KRN7000, and its analogues. More importantly, the use of a silicon tethered intramolecular glycosylation reaction gave easy access to the diglycosyl ceramide Gal(alpha1-->2)GalCer, which has been shown to require uptake and processing to the biologically active alpha-GalCer derivative.
spellingShingle Veerapen, N
Brigl, M
Garg, S
Cerundolo, V
Cox, L
Brenner, M
Besra, G
Synthesis and biological activity of alpha-galactosyl ceramide KRN7000 and galactosyl (alpha1-->2) galactosyl ceramide.
title Synthesis and biological activity of alpha-galactosyl ceramide KRN7000 and galactosyl (alpha1-->2) galactosyl ceramide.
title_full Synthesis and biological activity of alpha-galactosyl ceramide KRN7000 and galactosyl (alpha1-->2) galactosyl ceramide.
title_fullStr Synthesis and biological activity of alpha-galactosyl ceramide KRN7000 and galactosyl (alpha1-->2) galactosyl ceramide.
title_full_unstemmed Synthesis and biological activity of alpha-galactosyl ceramide KRN7000 and galactosyl (alpha1-->2) galactosyl ceramide.
title_short Synthesis and biological activity of alpha-galactosyl ceramide KRN7000 and galactosyl (alpha1-->2) galactosyl ceramide.
title_sort synthesis and biological activity of alpha galactosyl ceramide krn7000 and galactosyl alpha1 gt 2 galactosyl ceramide
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AT briglm synthesisandbiologicalactivityofalphagalactosylceramidekrn7000andgalactosylalpha1gt2galactosylceramide
AT gargs synthesisandbiologicalactivityofalphagalactosylceramidekrn7000andgalactosylalpha1gt2galactosylceramide
AT cerundolov synthesisandbiologicalactivityofalphagalactosylceramidekrn7000andgalactosylalpha1gt2galactosylceramide
AT coxl synthesisandbiologicalactivityofalphagalactosylceramidekrn7000andgalactosylalpha1gt2galactosylceramide
AT brennerm synthesisandbiologicalactivityofalphagalactosylceramidekrn7000andgalactosylalpha1gt2galactosylceramide
AT besrag synthesisandbiologicalactivityofalphagalactosylceramidekrn7000andgalactosylalpha1gt2galactosylceramide