A Convenient and Efficient Synthesis of Sialyl Lewis X

Kunihisa BABA; Noriyuki IWATA; Hitoshi HAMAJIMA; Takao IKAMI; Hideharu ISHIDA; Akira HASEGAWA; Makoto KISO

doi:10.1271/bbb.62.590

Bioscience, Biotechnology, and Biochemistry

Online ISSN : 1347-6947
Print ISSN : 0916-8451

Organic Chemistry Notes

A Convenient and Efficient Synthesis of Sialyl Lewis X

Kunihisa BABA, Noriyuki IWATA, Hitoshi HAMAJIMA, Takao IKAMI, Hideharu ISHIDA, Akira HASEGAWA, Makoto KISO

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Keywords: selectin, glycosylation, sialyl Lewis X

JOURNAL FREE ACCESS

1998 Volume 62 Issue 3 Pages 590-592

DOI https://doi.org/10.1271/bbb.62.590

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Abstract

A convenient synthesis of the sialyl Lewis X (sLe^x) tetrasaccharide, NeuAcα2-3Galβ1-4(Fucα1-3)GlcNAc (8), as a carbohydrate ligand for selectins is described. The key step is the reaction between NeuAcα2-3GalSMe (5) as a glycosyl donor and the suitably protected Fucα1-3GlcNAc derivative (4) as the glycosyl acceptor by using dimethyl(methylthio)sulfonium triflate (DMTST) as the promoter.

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