Chemoenzymatic synthesis of the oligosaccharide moiety of the tumor-associated antigen disialosyl globopentaosylceramide

Ingrid M E 't Hart; Tiehai Li; Margreet A Wolfert; Shuo Wang; Kelley W Moremen; Geert-Jan Boons

doi:10.1039/c9ob01368g

Chemoenzymatic synthesis of the oligosaccharide moiety of the tumor-associated antigen disialosyl globopentaosylceramide

Ingrid M E 't Hart, Tiehai Li, Margreet A Wolfert, Shuo Wang, Kelley W Moremen, Geert-Jan Boons

Department of Chemical Biology and Drug Discovery, Utrecht Institute for Pharmaceutical Sciences, and Bijvoet Center for Biomolecular Research, Utrecht University, 3584 CG Utrecht, The Netherlands. [email protected].
Complex Carbohydrate Research Center, University of Georgia, Athens, GA 30602, USA. [email protected].
Complex Carbohydrate Research Center, University of Georgia, Athens, GA 30602, USA. [email protected] and Department of Biochemistry and Molecular Biology, University of Georgia, Athens, GA 30602, USA.

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Abstract

Disialosyl globopentaosylceramide (DSGb5) is often expressed by renal cell carcinomas. To investigate properties of DSGb5, we have prepared its oligosaccharide moiety by chemically synthesizing Gb5 which was enzymatically sialylated using the mammalian sialyltransferases ST3Gal1 and ST6GalNAc5. Glycan microarray binding studies indicate that Siglec-7 does not recognize DSGb5, and preferentially binds Neu5Acα(2,8)Neu5Ac containing glycans.

Original language	English
Article number	1368g
Pages (from-to)	7304-7308
Number of pages	5
Journal	Organic & Biomolecular Chemistry
Volume	17
Issue number	31
DOIs	https://doi.org/10.1039/c9ob01368g
Publication status	Published - 24 Jul 2019

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title = "Chemoenzymatic synthesis of the oligosaccharide moiety of the tumor-associated antigen disialosyl globopentaosylceramide",

abstract = "Disialosyl globopentaosylceramide (DSGb5) is often expressed by renal cell carcinomas. To investigate properties of DSGb5, we have prepared its oligosaccharide moiety by chemically synthesizing Gb5 which was enzymatically sialylated using the mammalian sialyltransferases ST3Gal1 and ST6GalNAc5. Glycan microarray binding studies indicate that Siglec-7 does not recognize DSGb5, and preferentially binds Neu5Acα(2,8)Neu5Ac containing glycans.",

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AU - 't Hart, Ingrid M E

AU - Li, Tiehai

AU - Wolfert, Margreet A

AU - Wang, Shuo

AU - Moremen, Kelley W

AU - Boons, Geert-Jan

PY - 2019/7/24

Y1 - 2019/7/24

N2 - Disialosyl globopentaosylceramide (DSGb5) is often expressed by renal cell carcinomas. To investigate properties of DSGb5, we have prepared its oligosaccharide moiety by chemically synthesizing Gb5 which was enzymatically sialylated using the mammalian sialyltransferases ST3Gal1 and ST6GalNAc5. Glycan microarray binding studies indicate that Siglec-7 does not recognize DSGb5, and preferentially binds Neu5Acα(2,8)Neu5Ac containing glycans.

AB - Disialosyl globopentaosylceramide (DSGb5) is often expressed by renal cell carcinomas. To investigate properties of DSGb5, we have prepared its oligosaccharide moiety by chemically synthesizing Gb5 which was enzymatically sialylated using the mammalian sialyltransferases ST3Gal1 and ST6GalNAc5. Glycan microarray binding studies indicate that Siglec-7 does not recognize DSGb5, and preferentially binds Neu5Acα(2,8)Neu5Ac containing glycans.

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DO - 10.1039/c9ob01368g

M3 - Article

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JF - Organic & Biomolecular Chemistry

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M1 - 1368g

ER -

Chemoenzymatic synthesis of the oligosaccharide moiety of the tumor-associated antigen disialosyl globopentaosylceramide

Abstract

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