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

Molecular Cell Biology

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

13 Citations (Scopus)

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.

Original language	English
Pages (from-to)	3720-3725
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry
Volume	18
Issue number	11
DOIs	https://doi.org/10.1016/j.bmc.2010.03.062
Publication status	Published - 01-06-2010

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmc.2010.03.062

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@article{cbe1e852a8cc4a98b99e0f0d71a9b969,

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. ",

year = "2010",

month = jun,

day = "1",

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

language = "English",

volume = "18",

pages = "3720--3725",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier Ltd",

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TY - JOUR

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

UR - https://www.scopus.com/pages/publications/77953133153

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

C2 - 20409718

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

Abstract

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