Synthesis and biological activity of α-galactosyl ceramide KRN7000 and galactosyl (α1→2) galactosyl ceramide

Natacha Veerapen; M Brigl; S Garg; V Cerundolo; Liam Cox; MB Brenner; Gurdyal Besra

doi:10.1016/j.bmcl.2009.05.095

Synthesis and biological activity of α-galactosyl ceramide KRN7000 and galactosyl (α1→2) galactosyl ceramide

Natacha Veerapen, M Brigl, S Garg, V Cerundolo, Liam Cox, MB Brenner, Gurdyal Besra

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Abstract

We herein report a faster and less cumbersome synthesis of the biologically attractive, α-galactosyl ceramide (α-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(α1→2)GalCer, which has been shown to require uptake and processing to the biologically active α-GalCer derivative.

Original language	English
Pages (from-to)	4288-4291
Number of pages	4
Journal	Bioorganic & Medicinal Chemistry Letters
Volume	19
Issue number	15
DOIs	https://doi.org/10.1016/j.bmcl.2009.05.095
Publication status	Published - 1 Aug 2009

Keywords

iNKT
CD1d
KRN7000
Galactosyl(alpha 1-2)galactosyl

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http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pubmed&pubmedid=19502056Licence: Creative Commons: Attribution (CC BY)

Modulation of Immune Responses by aGalCer Analogues Through Differential Activation of CD1d-restricted NKT Cells
Besra, D. (Principal Investigator) & Lammas, T. (Co-Investigator)
Medical Research Council
1/06/05 → 30/11/09
Project: Research Councils

Cite this

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title = "Synthesis and biological activity of α-galactosyl ceramide KRN7000 and galactosyl (α1→2) galactosyl ceramide",

abstract = "We herein report a faster and less cumbersome synthesis of the biologically attractive, α-galactosyl ceramide (α-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(α1→2)GalCer, which has been shown to require uptake and processing to the biologically active α-GalCer derivative.",

keywords = "iNKT, CD1d, KRN7000, Galactosyl(alpha 1-2)galactosyl",

author = "Natacha Veerapen and M Brigl and S Garg and V Cerundolo and Liam Cox and MB Brenner and Gurdyal Besra",

year = "2009",

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doi = "10.1016/j.bmcl.2009.05.095",

language = "English",

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journal = "Bioorganic & Medicinal Chemistry Letters",

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T1 - Synthesis and biological activity of α-galactosyl ceramide KRN7000 and galactosyl (α1→2) galactosyl ceramide

AU - Veerapen, Natacha

AU - Brigl, M

AU - Garg, S

AU - Cerundolo, V

AU - Cox, Liam

AU - Brenner, MB

AU - Besra, Gurdyal

PY - 2009/8/1

Y1 - 2009/8/1

N2 - We herein report a faster and less cumbersome synthesis of the biologically attractive, α-galactosyl ceramide (α-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(α1→2)GalCer, which has been shown to require uptake and processing to the biologically active α-GalCer derivative.

AB - We herein report a faster and less cumbersome synthesis of the biologically attractive, α-galactosyl ceramide (α-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(α1→2)GalCer, which has been shown to require uptake and processing to the biologically active α-GalCer derivative.

KW - iNKT

KW - CD1d

KW - KRN7000

KW - Galactosyl(alpha 1-2)galactosyl

U2 - 10.1016/j.bmcl.2009.05.095

DO - 10.1016/j.bmcl.2009.05.095

M3 - Article

C2 - 19502056

VL - 19

SP - 4288

EP - 4291

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

IS - 15

ER -

Synthesis and biological activity of α-galactosyl ceramide KRN7000 and galactosyl (α1→2) galactosyl ceramide

Abstract

Keywords

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Modulation of Immune Responses by aGalCer Analogues Through Differential Activation of CD1d-restricted NKT Cells

Cite this