Synthesis and binding analysis of unique AG2 pentasaccharide to human Siglec-2 using NMR techniques

Shinya Hanashima; Ken ichi Sato; Yuko Naito; Hiromu Takematsu; Yasunori Kozutsumi; Yukishige Ito; Yoshiki Yamaguchi

doi:10.1016/j.bmc.2010.03.062

Synthesis and binding analysis of unique AG2 pentasaccharide to human Siglec-2 using NMR techniques

Shinya Hanashima
, Ken ichi Sato
, Yuko Naito
, Hiromu Takematsu
, Yasunori Kozutsumi
, Yukishige Ito
, Yoshiki Yamaguchi

免疫医科学

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

13 被引用数 (Scopus)

抄録

Siglec-2 is a mammalian sialic acid binding protein expressed on B-cell surfaces and is involved in the modulation of B-cell mediated immune response. We synthesized a unique starfish ganglioside, AG2 pentasaccharide Galfβ(1-3)Galpα(1-4)Neu5Acα(2-3)Galpβ(1-4)Glcp, and found that the synthetic pentasaccharide binds to human Siglec-2 by performing ¹H NMR experiments. Saturation transfer difference NMR experiments indicated that the C7-C9 side-chain and the acetamide moiety of the central sialic acid residue were located in the binding face of human Siglec-2. We determined the binding epitope of AG2 pentasaccharide to human Siglec-2, as the Galpα(1-4)Neu5Acα(2-3)Galp unit.

本文言語	英語
ページ（範囲）	3720-3725
ページ数	6
ジャーナル	Bioorganic and Medicinal Chemistry
巻	18
号	11
DOI	https://doi.org/10.1016/j.bmc.2010.03.062
出版ステータス	出版済み - 01-06-2010

All Science Journal Classification (ASJC) codes

生化学
分子医療
分子生物学
薬科学
創薬
臨床生化学
有機化学

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10.1016/j.bmc.2010.03.062

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title = "Synthesis and binding analysis of unique AG2 pentasaccharide to human Siglec-2 using NMR techniques",

abstract = "Siglec-2 is a mammalian sialic acid binding protein expressed on B-cell surfaces and is involved in the modulation of B-cell mediated immune response. We synthesized a unique starfish ganglioside, AG2 pentasaccharide Galfβ(1-3)Galpα(1-4)Neu5Acα(2-3)Galpβ(1-4)Glcp, and found that the synthetic pentasaccharide binds to human Siglec-2 by performing 1H NMR experiments. Saturation transfer difference NMR experiments indicated that the C7-C9 side-chain and the acetamide moiety of the central sialic acid residue were located in the binding face of human Siglec-2. We determined the binding epitope of AG2 pentasaccharide to human Siglec-2, as the Galpα(1-4)Neu5Acα(2-3)Galp unit.",

keywords = "Glycosylation, NMR, STD, Sialic acid, Siglec-2",

author = "Shinya Hanashima and Sato, \{Ken ichi\} and Yuko Naito and Hiromu Takematsu and Yasunori Kozutsumi and Yukishige Ito and Yoshiki Yamaguchi",

note = "Funding Information: We thank Ms. K. Matsumoto (RIKEN) for preparation of Siglec-2. We thank Dr. S. Akai (Kanagawa University) for helpful discussions. This work was supported by the Science Frontier Project of Kanagawa University and by Grants-in-Aid for Scientific Research for Young Scientists B (No. 20710171 to S.H.) from the Japan Society for the Promotion of Science . Global COE program of Osaka University from the Ministry of Education, Culture, Sports, Science, and Technology of Japan supported this work, in part. We thank Ms. K. Ueno and Ms. I. Hara for technical assistance. ",

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month = jun,

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doi = "10.1016/j.bmc.2010.03.062",

language = "English",

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journal = "Bioorganic and Medicinal Chemistry",

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T1 - Synthesis and binding analysis of unique AG2 pentasaccharide to human Siglec-2 using NMR techniques

AU - Hanashima, Shinya

AU - Sato, Ken ichi

AU - Naito, Yuko

AU - Takematsu, Hiromu

AU - Kozutsumi, Yasunori

AU - Ito, Yukishige

AU - Yamaguchi, Yoshiki

N1 - Funding Information: We thank Ms. K. Matsumoto (RIKEN) for preparation of Siglec-2. We thank Dr. S. Akai (Kanagawa University) for helpful discussions. This work was supported by the Science Frontier Project of Kanagawa University and by Grants-in-Aid for Scientific Research for Young Scientists B (No. 20710171 to S.H.) from the Japan Society for the Promotion of Science . Global COE program of Osaka University from the Ministry of Education, Culture, Sports, Science, and Technology of Japan supported this work, in part. We thank Ms. K. Ueno and Ms. I. Hara for technical assistance.

PY - 2010/6/1

Y1 - 2010/6/1

N2 - Siglec-2 is a mammalian sialic acid binding protein expressed on B-cell surfaces and is involved in the modulation of B-cell mediated immune response. We synthesized a unique starfish ganglioside, AG2 pentasaccharide Galfβ(1-3)Galpα(1-4)Neu5Acα(2-3)Galpβ(1-4)Glcp, and found that the synthetic pentasaccharide binds to human Siglec-2 by performing 1H NMR experiments. Saturation transfer difference NMR experiments indicated that the C7-C9 side-chain and the acetamide moiety of the central sialic acid residue were located in the binding face of human Siglec-2. We determined the binding epitope of AG2 pentasaccharide to human Siglec-2, as the Galpα(1-4)Neu5Acα(2-3)Galp unit.

AB - Siglec-2 is a mammalian sialic acid binding protein expressed on B-cell surfaces and is involved in the modulation of B-cell mediated immune response. We synthesized a unique starfish ganglioside, AG2 pentasaccharide Galfβ(1-3)Galpα(1-4)Neu5Acα(2-3)Galpβ(1-4)Glcp, and found that the synthetic pentasaccharide binds to human Siglec-2 by performing 1H NMR experiments. Saturation transfer difference NMR experiments indicated that the C7-C9 side-chain and the acetamide moiety of the central sialic acid residue were located in the binding face of human Siglec-2. We determined the binding epitope of AG2 pentasaccharide to human Siglec-2, as the Galpα(1-4)Neu5Acα(2-3)Galp unit.

KW - Glycosylation

KW - NMR

KW - STD

KW - Sialic acid

KW - Siglec-2

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UR - https://www.scopus.com/pages/publications/77953133153#tab=citedBy

U2 - 10.1016/j.bmc.2010.03.062

DO - 10.1016/j.bmc.2010.03.062

M3 - Article

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AN - SCOPUS:77953133153

SN - 0968-0896

VL - 18

SP - 3720

EP - 3725

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 11

ER -

Synthesis and binding analysis of unique AG2 pentasaccharide to human Siglec-2 using NMR techniques

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