Glycosylation of Nα-lauryl-O-(β-d-xylopyranosyl)-l- serinamide as a saccharide primer in cells

Yinan Wang; Tomoaki Kumazawa; Keisuke Shiba; Kenji Osumi; Mamoru Mizuno; Toshinori Sato

doi:10.1016/j.carres.2012.08.003

Glycosylation of N^α-lauryl-O-(β-d-xylopyranosyl)-l- serinamide as a saccharide primer in cells

Yinan Wang, Tomoaki Kumazawa, Keisuke Shiba, Kenji Osumi, Mamoru Mizuno, Toshinori Sato

Department of Biosciences and Informatics

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

Abstract

N^α-Lauryl-O-(β-d-xylopyranosyl)-l-serinamide (Xyl-Ser-C12) was synthesized as a saccharide primer to obtain oligosaccharides of glycosaminoglycan using the glycan biosynthetic potential of mouse osteosarcoma FBJ-S1 cells and Chinese hamster ovary (CHO) cells. The glycosylated products secreted into the culture medium were collected and analyzed by liquid chromatography-mass spectrometry and glycosidase digestion. The structure of the Xyl-Ser-C12 derivatives was investigated. Several glycosaminoglycan-type oligosaccharides, such as GalNAc-(GlcA-GlcNAc) _n-GlcA-Gal-Gal-Xyl-Ser-C12, were detected, and identified as intermediates of the biosynthesis of heparan sulfate glycosaminoglycans. Xyl-Ser-C12 exhibited greater acceptor activity for the glycosylation of glycosaminoglycan-type oligosaccharides than p-nitrophenyl-β-d- xylopyranoside.

Original language	English
Pages (from-to)	33-40
Number of pages	8
Journal	Carbohydrate Research
Volume	361
DOIs	https://doi.org/10.1016/j.carres.2012.08.003
Publication status	Published - 2012 Nov 1

Keywords

FBJ osteosarcoma
Glycosaminoglycan
Oligosaccharide
Saccharide primer

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

Access to Document

10.1016/j.carres.2012.08.003

Cite this

@article{0bab4c2b6ea24fed9ded24b6c992345a,

title = "Glycosylation of Nα-lauryl-O-(β-d-xylopyranosyl)-l- serinamide as a saccharide primer in cells",

abstract = "Nα-Lauryl-O-(β-d-xylopyranosyl)-l-serinamide (Xyl-Ser-C12) was synthesized as a saccharide primer to obtain oligosaccharides of glycosaminoglycan using the glycan biosynthetic potential of mouse osteosarcoma FBJ-S1 cells and Chinese hamster ovary (CHO) cells. The glycosylated products secreted into the culture medium were collected and analyzed by liquid chromatography-mass spectrometry and glycosidase digestion. The structure of the Xyl-Ser-C12 derivatives was investigated. Several glycosaminoglycan-type oligosaccharides, such as GalNAc-(GlcA-GlcNAc) n-GlcA-Gal-Gal-Xyl-Ser-C12, were detected, and identified as intermediates of the biosynthesis of heparan sulfate glycosaminoglycans. Xyl-Ser-C12 exhibited greater acceptor activity for the glycosylation of glycosaminoglycan-type oligosaccharides than p-nitrophenyl-β-d- xylopyranoside.",

keywords = "FBJ osteosarcoma, Glycosaminoglycan, Oligosaccharide, Saccharide primer",

author = "Yinan Wang and Tomoaki Kumazawa and Keisuke Shiba and Kenji Osumi and Mamoru Mizuno and Toshinori Sato",

note = "Funding Information: We thank Professor Tatsuya Yamagata for kindly providing FBJ-S1 cells and valuable discussions. This work was partly supported by the Global COE Project {\textquoteleft}{\textquoteleft}Global COE for Human Metabolomic Systems Biology{\textquoteright}{\textquoteright} (YW) from the Ministry of Education, Culture, Sports, Science and Technology and a Grant-in-aid for Challenging and Exploratory Research (2265108, TS) from the Japan Society for the Promotion of Science. ",

year = "2012",

month = nov,

day = "1",

doi = "10.1016/j.carres.2012.08.003",

language = "English",

volume = "361",

pages = "33--40",

journal = "Carbohydrate Research",

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T1 - Glycosylation of Nα-lauryl-O-(β-d-xylopyranosyl)-l- serinamide as a saccharide primer in cells

AU - Wang, Yinan

AU - Kumazawa, Tomoaki

AU - Shiba, Keisuke

AU - Osumi, Kenji

AU - Mizuno, Mamoru

AU - Sato, Toshinori

N1 - Funding Information: We thank Professor Tatsuya Yamagata for kindly providing FBJ-S1 cells and valuable discussions. This work was partly supported by the Global COE Project ‘‘Global COE for Human Metabolomic Systems Biology’’ (YW) from the Ministry of Education, Culture, Sports, Science and Technology and a Grant-in-aid for Challenging and Exploratory Research (2265108, TS) from the Japan Society for the Promotion of Science.

PY - 2012/11/1

Y1 - 2012/11/1

N2 - Nα-Lauryl-O-(β-d-xylopyranosyl)-l-serinamide (Xyl-Ser-C12) was synthesized as a saccharide primer to obtain oligosaccharides of glycosaminoglycan using the glycan biosynthetic potential of mouse osteosarcoma FBJ-S1 cells and Chinese hamster ovary (CHO) cells. The glycosylated products secreted into the culture medium were collected and analyzed by liquid chromatography-mass spectrometry and glycosidase digestion. The structure of the Xyl-Ser-C12 derivatives was investigated. Several glycosaminoglycan-type oligosaccharides, such as GalNAc-(GlcA-GlcNAc) n-GlcA-Gal-Gal-Xyl-Ser-C12, were detected, and identified as intermediates of the biosynthesis of heparan sulfate glycosaminoglycans. Xyl-Ser-C12 exhibited greater acceptor activity for the glycosylation of glycosaminoglycan-type oligosaccharides than p-nitrophenyl-β-d- xylopyranoside.

AB - Nα-Lauryl-O-(β-d-xylopyranosyl)-l-serinamide (Xyl-Ser-C12) was synthesized as a saccharide primer to obtain oligosaccharides of glycosaminoglycan using the glycan biosynthetic potential of mouse osteosarcoma FBJ-S1 cells and Chinese hamster ovary (CHO) cells. The glycosylated products secreted into the culture medium were collected and analyzed by liquid chromatography-mass spectrometry and glycosidase digestion. The structure of the Xyl-Ser-C12 derivatives was investigated. Several glycosaminoglycan-type oligosaccharides, such as GalNAc-(GlcA-GlcNAc) n-GlcA-Gal-Gal-Xyl-Ser-C12, were detected, and identified as intermediates of the biosynthesis of heparan sulfate glycosaminoglycans. Xyl-Ser-C12 exhibited greater acceptor activity for the glycosylation of glycosaminoglycan-type oligosaccharides than p-nitrophenyl-β-d- xylopyranoside.

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KW - Glycosaminoglycan

KW - Oligosaccharide

KW - Saccharide primer

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