Enzymatic reconstruction of glycosaminoglycan oligosaccharides

International Congress Series

Volumn 1223, Issue C, 2001, Pages 239-244

  Takagaki, Keiichi ^a   Kakizaki, Ikuko ^a   Iwafune, Mito ^a   Ishido, Keinosuke ^a   Endo, Masahiko ^a  

^a HIROSAKI UNIVERSITY   (Japan)

Author keywords

Enzymatic synthesis; Glycosaminoglycans; Testicular hyaluronidase; Transglycosylation

Indexed keywords

EID: 56749126934     PISSN: 05315131     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0531-5131(01)00440-X     Document Type: Article

References (24)

1. V.C. Hascall G.T. Hascall Proteoglycans E.D. Hay Cell Biology of Extracellular Matrix 1981 Plenum New York, NY 39 63
2. M. Höök L. Kjellén S. Johanssons J. Robinson Cell surface glycosaminoglycans Ann. Rev. Biochem. 53 1984 847 869
3. M. Petitou P. Duchaussoy I. Ledermann J. Choay P. Sinay Binding of heparin to antithrombin III: a chemical proof of the critical role played by a 3-sulfated 2-amino-2-deoxy- d -glucose residue Carbohydr. Res. 179 1988 163 172
4. Y. Ichikawa Monden H. Kuzuhara Synthesis of a heparin pentasaccharide fragment with a high affinity for antithrombin III employing cellobiose as a key starting material Tetrahedron Lett. 27 1986 611 614
5. F. Goto T. Ogawa Recent aspects of glycoconjugate synthesis: a synthetic approach to the linkage region of proteoglycans Pure Appl. Chem. 65 1993 793 801
6. E.J. Toone E.S. Simon M.D. Bednarski G.M. Whitesides Enzyme-catalyzed synthesis of carbohydrates Tetrahedron 45 1989 5365 5422
7. S. David C. Auge C. Gautheron Enzymic methods in preparative carbohydrate chemistry Carbohydr. Chem. Biochem. 49 1992 175 237
8. H.J.M. Gijsen L. Qiao W. Fitz C.-H. Wong Recent advances in the chemoenzymic synthesis of carbohydrates and carbohydrate mimetics Chem. Rev. 96 1996 443 473
9. T. Yasukouchi K. Fukase Y. Suda K. Takagaki M. Endo S. Kusumoto Enzymatic synthesis of 4-methylumbelliferyl glycosides of trisaccharide, and core tetrasaccharide, Gal(β1–3)Gal(β1–4)Xyl and GlcA(β1–3)Gal(β1–3)Gal(β1–4)Xyl, corresponding to the linkage region of proteglycans Bull. Chem. Soc. Jpn. 70 1997 2719 2725
10. J.-H. Yoon K. Ajisaka The synthesis of galactopyranosyl derivates with β-galactosidases of different origins Carbohydr. Res. 292 1996 153 163
11. T. Usui S. Morimoto Y. Hayakawa M. Kawaguchi T. Murata Y. Matahira Y. Nishida Regioselectivity of β- d -galactosyl-disaccharide formation using the β- d -galactosidase from Bacillus Circulans Carbohydr. Res. 285 1996 29 39
12. J. Abe N. Mizowaki S. Hizukuri K. Koizumi T. Utamura Synthesis of branched cyclomalto-oligosaccharides using Pseudomonas isoamylase Carbohydr. Res. 154 1986 81 92
13. T. Usui Y. Hayashi F. Nanjo Y. Ishido Enzymatic synthesis of p -nitrophenyl N , N ′, N ″, N ″, N ⁗-pentaacetyl-beta-chitopentaoside in water–methanol system: significance as a substrate for lysozyme assay Biochim. Biophys. Acta 953 1988 179 184
14. B. Weissmann The transglycosylation action of testicular hyaluronidase J. Biol. Chem. 216 1955 783 796
15. S. Highsmith T.H. Garvin Jr. D.M. Chipman Mechanism of action of bovine testicular hyaluronidase J. Biol. Chem. 250 1975 7473 7480
16. H. Saitoh K. Takagaki M. Majima T. Nakamura A. Matsuki M. Kasai H. Narita M. Endo Enzymic reconstruction of glycosaminoglycan oligosaccharide chain using the transglycosylation reaction of bovine testicular hyaluronidase J. Biol. Chem. 270 1995 3741 3747
17. P.J. Knudsen P.B. Eriksen M. Fenger K. Florentz High-performance liquid chromatography of hyaluronic acid and oligosaccharides produced by bovine testes hyaluronidase J. Chromatogr. 187 1980 373 379
18. K. Takagaki T. Nakamura J. Izumi H. Saitoh M. Endo I. Kato M. Majima Characterization of hydrolysis and transglycosylation by testicular hyaluronidase using ion-spray mass spectrometry Biochemistry 33 1994 6503 6507
19. B. Case M. Petitou M. Provasoli P. Sinay Conformational flexibility: a new concept for explaining binding and biological properties of iduroic acid-containing glycosaminoglycans Trends Biochem. Sci. 13 1988 221 225
20. K. Takagaki H. Munakata I. Kakizaki M. Majima M. Endo Enzymatic reconstruction of dermatan sulfate Biochem. Biophys. Res. Commun. 270 2000 588 593
21. J. Gossling Occurrence and pathogenicity of the Streptococcus milleri group Rev. Infect. Dis. 10 1988 257 285
22. M.T. Parker L.C. Ball Streptococci and Aerococci associated with systemic infection in man J. Med. Microbiol. 9 1976 275 302
23. K.L. Ruoff Streptococcus Anginous : the unrecognized pathogen Clin. Microbiol. Rev. 1 1988 102 108
24. K. Takagaki H. Munakata M. Majima I. Kakizaki M. Endo Chimeric glycosaminoglycan oligosaccharides synthesized by enzymatic reconstruction and their use in substrate specificity determination of Streptococcus hyaluronidase J. Biochem. 127 2000 695 702