HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS		QUICK SEARCH:   [advanced] Author: Keyword(s): Year:  Vol:  Page:

This Article Full Text Full Text (PDF) Alert me when this article is cited Alert me if a correction is posted Citation Map Services Email this article to a friend Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Download to citation manager Citing Articles Citing Articles via HighWire Citing Articles via Google Scholar Google Scholar Articles by Sugahara, K. Articles by Dell, A. Search for Related Content PubMed PubMed Citation Articles by Sugahara, K. Articles by Dell, A. Social Bookmarking                      What's this?

Volume 271, Number 43, Issue of October 25, 1996 pp. 26745-26754
©1996 by The American Society for Biochemistry and Molecular Biology, Inc.

---

Novel Sulfated Oligosaccharides Containing 3-O-Sulfated Glucuronic Acid from King Crab Cartilage Chondroitin Sulfate K
UNEXPECTED DEGRADATION BY CHONDROITINASE ABC

(Received for publication, March 20, 1996, and in revised form, June 10, 1996)

From the Department of Biochemistry, Kobe Pharmaceutical University, Higashinada-ku, Kobe 658 and the ^§ Department of Chemistry, Ochanomizu University, Tokyo 112, Japan

Stuart M. Haslam , Howard R. Morris and Anne Dell

From the Department of Biochemistry, Imperial College, London SW7 2AZ, United Kingdom

We prepared a series of oligosaccharides from king crab cartilage chondroitin sulfate K after exhaustive digestion with testicular hyaluronidase, and determined the structures of four tetrasaccharides and a pentasaccharide by fast atom bombardment mass spectrometry, high performance liquid chromatography analysis of chondroitinase AC-II digests, and 500-MHz ¹H NMR spectroscopy. The tetrasaccharides shared the common core structure GlcA1-3GalNAc1-4GlcA1-3GalNAc with various sulfation profiles. One structure was GlcA1-3GalNAc(4S)1-4GlcA1-3GalNAc(4S), whereas three of them have the following hitherto unreported structures including a novel glucuronate 3-O-sulfate: GlcA(3S)1-3GalNAc(4S)1-4GlcA1-3GalNAc(4S), GlcA1-3GalNAc(4S)1-4GlcA(3S)1-3GalNAc(4S), and GlcA(3S)1-3GalNAc(4S)1-4GlcA(3S)1-3GalNAc(4S), where 3S or 4S represents 3-O- or 4-O-sulfate, respectively. The structure of the pentasaccharide was determined as GlcA(3S)1-3GalNAc(4S)1-4GlcA(3S)1- 3GalNAc(4S)1-4GlcA. Chondroitinase ABC digestion of the tetrasaccharides with GlcA(3S) at the internal position destroyed the disaccharide unit containing GlcA(3S) derived from the reducing side and resulted in only the disaccharide unit from the non-reducing side. In contrast, these tetrasaccharides remained totally resistant to chondroitinase AC-II. The results indicated that it is necessary to reevaluate the disaccharide composition of chondroitin sulfate poly- or oligosaccharides purified from various biological sources, since they were usually determined after chondroitinase ABC digestion. It is probable that the structures containing GlcA(3S) would not have been detected.

CiteULike    Complore    Connotea    Del.icio.us    Digg    Reddit    Technorati    What's this?

This article has been cited by other articles:

				R. Lawrence, S. K. Olson, R. E. Steele, L. Wang, R. Warrior, R. D. Cummings, and J. D. Esko Evolutionary Differences in Glycosaminoglycan Fine Structure Detected by Quantitative Glycan Reductive Isotope Labeling J. Biol. Chem., November 28, 2008; 283(48): 33674 - 33684. [Abstract] [Full Text] [PDF]

				D. Fongmoon, A. K. Shetty, Basappa, S. Yamada, M. Sugiura, P. Kongtawelert, and K. Sugahara Chondroitinase-mediated Degradation of Rare 3-O-Sulfated Glucuronic Acid in Functional Oversulfated Chondroitin Sulfate K and E J. Biol. Chem., December 21, 2007; 282(51): 36895 - 36904. [Abstract] [Full Text] [PDF]

				S. S Deepa, S. Yamada, S. Fukui, and K. Sugahara Structural determination of novel sulfated octasaccharides isolated from chondroitin sulfate of shark cartilage and their application for characterizing monoclonal antibody epitopes Glycobiology, June 1, 2007; 17(6): 631 - 645. [Abstract] [Full Text] [PDF]

				K. R. Taylor and R. L. Gallo Glycosaminoglycans and their proteoglycans: host-associated molecular patterns for initiation and modulation of inflammation FASEB J, January 1, 2006; 20(1): 9 - 22. [Abstract] [Full Text] [PDF]

				K. Bergefall, E. Trybala, M. Johansson, T. Uyama, S. Naito, S. Yamada, H. Kitagawa, K. Sugahara, and T. Bergstrom Chondroitin Sulfate Characterized by the E-disaccharide Unit Is a Potent Inhibitor of Herpes Simplex Virus Infectivity and Provides the Virus Binding Sites on gro2C Cells J. Biol. Chem., September 16, 2005; 280(37): 32193 - 32199. [Abstract] [Full Text] [PDF]

				D. J. Rigden and M. J. Jedrzejas Structures of Streptococcus pneumoniae Hyaluronate Lyase in Complex with Chondroitin and Chondroitin Sulfate Disaccharides: INSIGHTS INTO SPECIFICITY AND MECHANISM OF ACTION J. Biol. Chem., December 12, 2003; 278(50): 50596 - 50606. [Abstract] [Full Text] [PDF]

				M. Hikino, T. Mikami, A. Faissner, A.-C. E. S. Vilela-Silva, M. S. G. Pavao, and K. Sugahara Oversulfated Dermatan Sulfate Exhibits Neurite Outgrowth-promoting Activity toward Embryonic Mouse Hippocampal Neurons: IMPLICATIONS OF DERMATAN SULFATE IN NEURITOGENESIS IN THE BRAIN J. Biol. Chem., October 31, 2003; 278(44): 43744 - 43754. [Abstract] [Full Text] [PDF]

				S. Ohtake, K. Kimata, and O. Habuchi A Unique Nonreducing Terminal Modification of Chondroitin Sulfate by N-Acetylgalactosamine 4-Sulfate 6-O-Sulfotransferase J. Biol. Chem., October 3, 2003; 278(40): 38443 - 38452. [Abstract] [Full Text] [PDF]

				T. Mikami, S. Mizumoto, N. Kago, H. Kitagawa, and K. Sugahara Specificities of Three Distinct Human Chondroitin/Dermatan N-Acetylgalactosamine 4-O-Sulfotransferases Demonstrated Using Partially Desulfated Dermatan Sulfate as an Acceptor: IMPLICATION OF DIFFERENTIAL ROLES IN DERMATAN SULFATE BIOSYNTHESIS J. Biol. Chem., September 19, 2003; 278(38): 36115 - 36127. [Abstract] [Full Text] [PDF]

				S. S. Deepa, Y. Umehara, S. Higashiyama, N. Itoh, and K. Sugahara Specific Molecular Interactions of Oversulfated Chondroitin Sulfate E with Various Heparin-binding Growth Factors. IMPLICATIONS AS A PHYSIOLOGICAL BINDING PARTNER IN THE BRAIN AND OTHER TISSUES J. Biol. Chem., November 8, 2002; 277(46): 43707 - 43716. [Abstract] [Full Text] [PDF]

				K. Pojasek, R. Raman, P. Kiley, G. Venkataraman, and R. Sasisekharan Biochemical Characterization of the Chondroitinase B Active Site J. Biol. Chem., August 16, 2002; 277(34): 31179 - 31186. [Abstract] [Full Text] [PDF]

				T. Ninomiya, N. Sugiura, A. Tawada, K. Sugimoto, H. Watanabe, and K. Kimata Molecular Cloning and Characterization of Chondroitin Polymerase from Escherichia coli Strain K4 J. Biol. Chem., June 7, 2002; 277(24): 21567 - 21575. [Abstract] [Full Text] [PDF]

				R. M. Lauder, T. N. Huckerby, and I. A. Nieduszynski A fingerprinting method for chondroitin/dermatan sulfate and hyaluronan oligosaccharides Glycobiology, April 1, 2000; 10(4): 393 - 401. [Abstract] [Full Text] [PDF]

				J. Liu, N. W. Shworak, P. Sinay, J. J. Schwartz, L. Zhang, L. M. S. Fritze, and R. D. Rosenberg Expression of Heparan Sulfate D-Glucosaminyl 3-O-Sulfotransferase Isoforms Reveals Novel Substrate Specificities J. Biol. Chem., February 19, 1999; 274(8): 5185 - 5192. [Abstract] [Full Text] [PDF]

				H. Kitagawa, K. Tsutsumi, Y. Tone, and K. Sugahara Developmental Regulation of the Sulfation Profile of Chondroitin Sulfate Chains in the Chicken Embryo Brain J. Biol. Chem., December 12, 1997; 272(50): 31377 - 31381. [Abstract] [Full Text] [PDF]

				A. Kinoshita, S. Yamada, S. M. Haslam, H. R. Morris, A. Dell, and K. Sugahara Novel Tetrasaccharides Isolated from Squid Cartilage Chondroitin Sulfate E Contain Unusual Sulfated Disaccharide Units GlcA(3-O-sulfate)beta 1-3GalNAc(6-O-sulfate) or GlcA(3-O-sulfate)beta 1-3GalNAc(4,6-O-disulfate) J. Biol. Chem., August 8, 1997; 272(32): 19656 - 19665. [Abstract] [Full Text] [PDF]

				C. Ueoka, N. Kaneda, I. Okazaki, S. Nadanaka, T. Muramatsu, and K. Sugahara Neuronal Cell Adhesion, Mediated by the Heparin-binding Neuroregulatory Factor Midkine, Is Specifically Inhibited by Chondroitin Sulfate E. STRUCTURAL AND FUNCTIONAL IMPLICATIONS OF THE OVER-SULFATED CHONDROITIN SULFATE J. Biol. Chem., November 22, 2000; 275(48): 37407 - 37413. [Abstract] [Full Text] [PDF]

				H. Kawashima, M. Hirose, J. Hirose, D. Nagakubo, A. H. K. Plaas, and M. Miyasaka Binding of a Large Chondroitin Sulfate/Dermatan Sulfate Proteoglycan, Versican, to L-selectin, P-selectin, and CD44 J. Biol. Chem., November 3, 2000; 275(45): 35448 - 35456. [Abstract] [Full Text] [PDF]

				K. Tsuchida, J. Shioi, S. Yamada, G. Boghosian, A. Wu, H. Cai, K. Sugahara, and N. K. Robakis Appican, the Proteoglycan Form of the Amyloid Precursor Protein, Contains Chondroitin Sulfate E in the Repeating Disaccharide Region and 4-O-Sulfated Galactose in the Linkage Region J. Biol. Chem., September 28, 2001; 276(40): 37155 - 37160. [Abstract] [Full Text] [PDF]