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

Veerapen N, Brigl M, Garg S, Cerundolo V, Cox LR, Brenner MB, Besra GS - Bioorg. Med. Chem. Lett. (2009)

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: School of Biosciences, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK.

ABSTRACT
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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Reagents and conditions: (a) TBDPSCl, Pyr, quant; (b) BzCl, Pyr, 88%; (c) TBAF, THF, 82%.
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fig2: Reagents and conditions: (a) TBDPSCl, Pyr, quant; (b) BzCl, Pyr, 88%; (c) TBAF, THF, 82%.

Mentions: We first synthesized the phytosphingosine acceptor 516 from (2S,3S,4R)-2-azido-1, 3, 4-octadecanetriol17 in three steps as described in Scheme 1.


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

Veerapen N, Brigl M, Garg S, Cerundolo V, Cox LR, Brenner MB, Besra GS - Bioorg. Med. Chem. Lett. (2009)

Reagents and conditions: (a) TBDPSCl, Pyr, quant; (b) BzCl, Pyr, 88%; (c) TBAF, THF, 82%.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC2722241&req=5

fig2: Reagents and conditions: (a) TBDPSCl, Pyr, quant; (b) BzCl, Pyr, 88%; (c) TBAF, THF, 82%.
Mentions: We first synthesized the phytosphingosine acceptor 516 from (2S,3S,4R)-2-azido-1, 3, 4-octadecanetriol17 in three steps as described in Scheme 1.

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: School of Biosciences, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK.

ABSTRACT
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.

Show MeSH