Isolation and Structural Determination of Novel Sulfated Hexasaccharides from Squid Cartilage Chondroitin Sulfate E That Exhibits Neuroregulatory Activities

DOI Web Site PubMed 被引用文献2件
  • Akiko Kinoshita
    Department of Biochemistry, Kobe Pharmaceutical University, Higashinada-ku, Kobe 658-8558, Japan, and Department of Biochemistry, Imperial College, London SW7 2AZ, United Kingdom
  • Shuhei Yamada
    Department of Biochemistry, Kobe Pharmaceutical University, Higashinada-ku, Kobe 658-8558, Japan, and Department of Biochemistry, Imperial College, London SW7 2AZ, United Kingdom
  • Stuart M. Haslam
    Department of Biochemistry, Kobe Pharmaceutical University, Higashinada-ku, Kobe 658-8558, Japan, and Department of Biochemistry, Imperial College, London SW7 2AZ, United Kingdom
  • Howard R. Morris
    Department of Biochemistry, Kobe Pharmaceutical University, Higashinada-ku, Kobe 658-8558, Japan, and Department of Biochemistry, Imperial College, London SW7 2AZ, United Kingdom
  • Anne Dell
    Department of Biochemistry, Kobe Pharmaceutical University, Higashinada-ku, Kobe 658-8558, Japan, and Department of Biochemistry, Imperial College, London SW7 2AZ, United Kingdom
  • Kazuyuki Sugahara
    Department of Biochemistry, Kobe Pharmaceutical University, Higashinada-ku, Kobe 658-8558, Japan, and Department of Biochemistry, Imperial College, London SW7 2AZ, United Kingdom

書誌事項

公開日
2001-09-29
DOI
  • 10.1021/bi015577n
公開者
American Chemical Society (ACS)

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説明

Squid cartilage chondroitin sulfate E (CS-E) exhibits various biological activities, including anticoagulant activities, lymphoid regulatory activities, and neuroregulatory activities [Ueoka, C., Kaneda, N., Okazaki, I., Nadanaka, S., Muramatsu, T., and Sugahara, K. (2000) J. Biol. Chem. 275, 37407-37413]. These activities are expressed through molecular interactions with specific proteins, including heparin cofactor II, selectins, CD44, chemokines, and the heparin-binding growth factor midkine. Hence, the sugar sequence information is essential for a better understanding of the CS-E functions. Previously, several novel tetrasaccharides containing the unreported 3-O-sulfated glucuronic acid (GlcA) were isolated after digestion of squid cartilage CS-E with testicular hyaluronidase. In this study, hexasaccharides were isolated to obtain more detailed sequence information, especially around the GlcA(3-O-sulfate) residue, and were characterized by fast atom bombardment mass spectrometry and 500 or 600 MHz (1)H NMR spectroscopy. The findings demonstrate one tetrasulfated and five pentasulfated hexasaccharide sequences, five of them being novel. They were composed of three disaccharide building units of either A [GlcA(beta1-3)GalNAc(4-O-sulfate)], E [GlcA(beta1-3)GalNAc(4,6-O-disulfate)], K [GlcA(3-O-sulfate)(beta1-3)GalNAc(4-O-sulfate)], L [GlcA(3-O-sulfate)(beta1-3)GalNAc(6-O-sulfate)], or M [GlcA(3-O-sulfate)(beta1-3)GalNAc(4,6-O-disulfate)], forming E-A-A, M-A-A, K-L-A, E-E-A, K-K-A, and A-M-A hexasaccharide sequences. The K-L tetrasaccharide sequence is to date unreported. The isolated sequences appear to indicate the occurrence of an unreported GlcA 3-O-sulfotransferase specific for chondroitin sulfate. The obtained sequence information will be useful for investigating the structure-function relationship and biosynthesis of CS-E.

収録刊行物

  • Biochemistry

    Biochemistry 40 (42), 12654-12665, 2001-09-29

    American Chemical Society (ACS)

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