Nitropyridyl glycosides: new glycosyl donors for enzymatic transglycosylation

被引:25
作者
Yasukochi, T [1 ]
Inaba, C [1 ]
Fukase, K [1 ]
Kusumoto, S [1 ]
机构
[1] Osaka Univ, Grad Sch Sci, Dept Chem, Toyonaka, Osaka 5600043, Japan
基金
日本学术振兴会;
关键词
glycosidase; transglycosylation; glycosyl donor; 3-nitro-2-pyridyl glycoside;
D O I
10.1016/S0040-4039(99)01279-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New glycosyl donors, 3-nitro-2-pyridyl and 5-nitro-2-pyridyl glycosides, proved to be effective for transglycosylation reaction catalyzed by glycosidases, such as beta-galactosidase, B-glucosidase, and N-acetyl-beta-hexosaminidase. The high solubility in water and the high reactivity of the nitropyridyl glycosides enabled the reactions under high concentrations of the donors and consequently rapid glycosyl transfer to glycosyl accepters. The yields of the transglycosylated products with the nitropyridyl glycosides were much higher than those with conventional p-nitrophenyl glycosides. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6585 / 6589
页数:5
相关论文
共 34 条
  • [1] An α-L-fucosidase from Penicillium multicolor as a candidate enzyme for the synthesis of a (1→3)-linked fucosyl oligosaccharides by transglycosylation
    Ajisaka, K
    Fujimoto, H
    Miyasato, M
    [J]. CARBOHYDRATE RESEARCH, 1998, 309 (01) : 125 - 129
  • [2] Stereochemical course and reaction products of the action of beta-xylosidase from Thermoanaerobacterium saccharolyticum strain B6A-RI
    Armand, S
    Vieille, C
    Gey, C
    Heyraud, A
    Zeikus, JG
    Henrissat, B
    [J]. EUROPEAN JOURNAL OF BIOCHEMISTRY, 1996, 236 (02): : 706 - 713
  • [3] AN IMPROVED STRATEGY FOR THE STEREOSELECTIVE SYNTHESIS OF GLYCOSIDES USING GLYCOSIDASES AS CATALYSTS
    BAKER, A
    TURNER, NJ
    WEBBERLEY, MC
    [J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (12) : 2517 - 2522
  • [4] Chemical and enzymatic synthesis of glycoconjugates 3: Synthesis of lactosamine by thermophilic galactosidase catalyzed galactosylation on a multigram scale
    Fang, JW
    Xie, WH
    Li, J
    Wang, PG
    [J]. TETRAHEDRON LETTERS, 1998, 39 (09) : 919 - 922
  • [5] Chemoenzymatic synthesis of Gal(beta 1-3)Gal(beta 1-4)Xyl(beta)-L-Ser and Gal(beta 1-3)Gal(beta 1-4)Xyl(beta)-MU by the use of beta-D-galactosidase
    Fukase, K
    Yasukochi, T
    Suda, Y
    Yoshida, M
    Kusumoto, S
    [J]. TETRAHEDRON LETTERS, 1996, 37 (37) : 6763 - 6766
  • [6] Enzymatic glycosidation in dry media under microwave irradiation
    GeloPujic, M
    GuibeJampel, E
    Loupy, A
    Trincone, A
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (07): : 1001 - 1002
  • [7] SYNTHESIS OF (+)-AVERMECTIN-B1A
    HANESSIAN, S
    UGOLINI, A
    DUBE, D
    HODGES, PJ
    ANDRE, C
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (10) : 2776 - 2778
  • [8] A practical method for the synthesis of N-acetyl-D-lactosamine derivatives by the tandem use of galactose oxidase and beta-galactosidase
    Kimura, T
    Takayama, S
    Huang, HM
    Wong, CH
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (20): : 2348 - 2350
  • [9] Glycosylation employing bio-systems: from enzymes to whole cells
    Kren, V
    Thiem, J
    [J]. CHEMICAL SOCIETY REVIEWS, 1997, 26 (06) : 463 - 473
  • [10] Chemical and enzymatic synthesis of glycoconjugates -: 4.: Control of regioselectivity in high yielding synthesis of (β-D-fucopyranosyl)-O-D-xylopyranosyl disaccharides using a CLONEZYME™ thermophilic glycosidase
    Li, J
    Robertson, DE
    Short, JM
    Wang, PG
    [J]. TETRAHEDRON LETTERS, 1998, 39 (49) : 8963 - 8966