Glycosylation of dodecyl 2-acetamido-2-deoxy-β-d-glucopyranoside and dodecyl β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-d-glucopyranoside as saccharide primers in cells

Toshinori Sato; Minako Takashiba; Rumi Hayashi; Xingyu Zhu; Tatsuya Yamagata

doi:10.1016/j.carres.2008.01.022

Glycosylation of dodecyl 2-acetamido-2-deoxy-β-d-glucopyranoside and dodecyl β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-d-glucopyranoside as saccharide primers in cells

Toshinori Sato, Minako Takashiba, Rumi Hayashi, Xingyu Zhu, Tatsuya Yamagata

Department of Biosciences and Informatics

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

15 Citations (Scopus)

Abstract

Syntheses of oligosaccharides expressed on cells are indispensable for the improvement of the functional analyses of the oligosaccharides and their applications. We are developing saccharide primers for synthesizing oligosaccharides using living cells. In this study, dodecyl 2-acetamido-2-deoxy-β-d-glucopyranoside (GlcNAc-C12) and dodecyl β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-d-glucopyranoside (LacNAc-C12) were examined for their abilities to prime the syntheses of neolacto-series oligosaccharides in HL60 cells. When GlcNAc-C12 was incubated with HL60 cells in serum-free medium for 2 days, 14 kinds of glycosylated products were collected from the culture medium. They were separated by high-performance liquid chromatography. The sequences of the products were determined to be neolacto-series oligosaccharides including Lewis^X, sialyl Lewis^X, polylactosamine, and sialylpolylactosamine by mass spectrometry. GlcNAc-C12 was also glycosylated by B16 cells and gave sialyllactosamine. Furthermore, LacNAc-C12 gave similar glycosylated products to GlcNAc-C12.

Original language	English
Pages (from-to)	831-838
Number of pages	8
Journal	Carbohydrate Research
Volume	343
Issue number	5
DOIs	https://doi.org/10.1016/j.carres.2008.01.022
Publication status	Published - 2008 Apr 7

Keywords

Animal cells
Glycosylation
N-Acetylglucosamine
N-Acetyllactosamine
Oligosaccharide
Saccharide primer

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

Access to Document

10.1016/j.carres.2008.01.022

Cite this

Glycosylation of dodecyl 2-acetamido-2-deoxy-β-d-glucopyranoside and dodecyl β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-d-glucopyranoside as saccharide primers in cells. / Sato, Toshinori; Takashiba, Minako; Hayashi, Rumi et al.
In: Carbohydrate Research, Vol. 343, No. 5, 07.04.2008, p. 831-838.

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

@article{18a9d83942674537aa64ae639046131e,

title = "Glycosylation of dodecyl 2-acetamido-2-deoxy-β-d-glucopyranoside and dodecyl β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-d-glucopyranoside as saccharide primers in cells",

abstract = "Syntheses of oligosaccharides expressed on cells are indispensable for the improvement of the functional analyses of the oligosaccharides and their applications. We are developing saccharide primers for synthesizing oligosaccharides using living cells. In this study, dodecyl 2-acetamido-2-deoxy-β-d-glucopyranoside (GlcNAc-C12) and dodecyl β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-d-glucopyranoside (LacNAc-C12) were examined for their abilities to prime the syntheses of neolacto-series oligosaccharides in HL60 cells. When GlcNAc-C12 was incubated with HL60 cells in serum-free medium for 2 days, 14 kinds of glycosylated products were collected from the culture medium. They were separated by high-performance liquid chromatography. The sequences of the products were determined to be neolacto-series oligosaccharides including LewisX, sialyl LewisX, polylactosamine, and sialylpolylactosamine by mass spectrometry. GlcNAc-C12 was also glycosylated by B16 cells and gave sialyllactosamine. Furthermore, LacNAc-C12 gave similar glycosylated products to GlcNAc-C12.",

keywords = "Animal cells, Glycosylation, N-Acetylglucosamine, N-Acetyllactosamine, Oligosaccharide, Saccharide primer",

author = "Toshinori Sato and Minako Takashiba and Rumi Hayashi and Xingyu Zhu and Tatsuya Yamagata",

note = "Funding Information: This work was partly supported by funds from the Program for Promotion of Basic Research Activities for Innovative Biosciences, and the Special Coordination of Funds for Promoting Science and Technology from the Ministry of Education, Culture, Sports, Science and Technology, the Japanese Government (T.S.). ",

year = "2008",

month = apr,

day = "7",

doi = "10.1016/j.carres.2008.01.022",

language = "English",

volume = "343",

pages = "831--838",

journal = "Carbohydrate Research",

issn = "0008-6215",

publisher = "Elsevier BV",

number = "5",

}

TY - JOUR

T1 - Glycosylation of dodecyl 2-acetamido-2-deoxy-β-d-glucopyranoside and dodecyl β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-d-glucopyranoside as saccharide primers in cells

AU - Sato, Toshinori

AU - Takashiba, Minako

AU - Hayashi, Rumi

AU - Zhu, Xingyu

AU - Yamagata, Tatsuya

N1 - Funding Information: This work was partly supported by funds from the Program for Promotion of Basic Research Activities for Innovative Biosciences, and the Special Coordination of Funds for Promoting Science and Technology from the Ministry of Education, Culture, Sports, Science and Technology, the Japanese Government (T.S.).

PY - 2008/4/7

Y1 - 2008/4/7

N2 - Syntheses of oligosaccharides expressed on cells are indispensable for the improvement of the functional analyses of the oligosaccharides and their applications. We are developing saccharide primers for synthesizing oligosaccharides using living cells. In this study, dodecyl 2-acetamido-2-deoxy-β-d-glucopyranoside (GlcNAc-C12) and dodecyl β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-d-glucopyranoside (LacNAc-C12) were examined for their abilities to prime the syntheses of neolacto-series oligosaccharides in HL60 cells. When GlcNAc-C12 was incubated with HL60 cells in serum-free medium for 2 days, 14 kinds of glycosylated products were collected from the culture medium. They were separated by high-performance liquid chromatography. The sequences of the products were determined to be neolacto-series oligosaccharides including LewisX, sialyl LewisX, polylactosamine, and sialylpolylactosamine by mass spectrometry. GlcNAc-C12 was also glycosylated by B16 cells and gave sialyllactosamine. Furthermore, LacNAc-C12 gave similar glycosylated products to GlcNAc-C12.

AB - Syntheses of oligosaccharides expressed on cells are indispensable for the improvement of the functional analyses of the oligosaccharides and their applications. We are developing saccharide primers for synthesizing oligosaccharides using living cells. In this study, dodecyl 2-acetamido-2-deoxy-β-d-glucopyranoside (GlcNAc-C12) and dodecyl β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-d-glucopyranoside (LacNAc-C12) were examined for their abilities to prime the syntheses of neolacto-series oligosaccharides in HL60 cells. When GlcNAc-C12 was incubated with HL60 cells in serum-free medium for 2 days, 14 kinds of glycosylated products were collected from the culture medium. They were separated by high-performance liquid chromatography. The sequences of the products were determined to be neolacto-series oligosaccharides including LewisX, sialyl LewisX, polylactosamine, and sialylpolylactosamine by mass spectrometry. GlcNAc-C12 was also glycosylated by B16 cells and gave sialyllactosamine. Furthermore, LacNAc-C12 gave similar glycosylated products to GlcNAc-C12.

KW - Animal cells

KW - Glycosylation

KW - N-Acetylglucosamine

KW - N-Acetyllactosamine

KW - Oligosaccharide

KW - Saccharide primer

UR - http://www.scopus.com/inward/record.url?scp=39849084206&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=39849084206&partnerID=8YFLogxK

U2 - 10.1016/j.carres.2008.01.022

DO - 10.1016/j.carres.2008.01.022

M3 - Article

C2 - 18262174

AN - SCOPUS:39849084206

SN - 0008-6215

VL - 343

SP - 831

EP - 838

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 5

ER -

Glycosylation of dodecyl 2-acetamido-2-deoxy-β-d-glucopyranoside and dodecyl β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-d-glucopyranoside as saccharide primers in cells

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this