ブタ肝臓由来α-L-フコシダーゼによるα-L-フコシルオリゴ糖の位置選択的合成 Regioselectivity of α-L-fucopyranosyloligosaccharide Formation by the α-L-Fucosidase from Porcine Liver

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Author(s)

    • 曽 暁雄 ZENG Xiaoxiong
    • 静岡大学農学部応用生物化学科 Department of Applied Biological Chemistry, Faculty of Agriculture, Shizuoka University
    • 碓氷 泰市 USUI Taichi
    • 静岡大学農学部応用生物化学科 Department of Applied Biological Chemistry, Faculty of Agriculture, Shizuoka University

Abstract

p-ニトロフェニルα一レフコピラノシドをドナーとして,ブタ肝臓由来の部分精製α-L-フコシダーゼを用いて,a-L一フコシル化二糖と三糖の位置選択的合成を行った.p一ニトロフェニルβ-D一ガラクトピラノシド(Ga1β-pNP)をアクセプターとした転移反応においては,主生成物Fucα1→2Galβ-pNPとともに(1→3)と(1→6)結合異性体を生成し,それぞれの生成比は58:22:20,全収率はドナー当たり40.6%であった.一方,ρ一ニトロフェニルβ一D一グルコピラノシドをアクセプターとした場合は,主生成物は(1→3)結合二糖であり,同時に(1→2),(1→4),(1→6)結合異性体も生成した.p一ニトロフェニルβ-D一ラクトシドをアクセプターとした場合は,Ga1β一ρNPアクセプター同様に本二糖Ga1残基の0-2',0-3ノ,0・6ノ位がフコシル化されるが,その位置選択性および収率は著しく低下した.p一ニトロフェニル2一アセトアミドー2一デオキシーβ-D一グルコピラノシドをアクセプターとした反応においては,主転移物は(1→3)と(1→4)結合二糖であった.

α-L-Fucosidase partially purified from porcine liver was used for the regioselective synthesis of α-L-fucopyranosyl di- and trisaccharides with p-nitrophenyl a-L-fucopyranoside (Fuc α-pNP) as the donor. In a transglycosylation reaction with p-nitrophenyl β-D-galactopyranoside (Gal β-pNP) as the accep-tor, the enzyme formed mainly Fuc a1→2Gal, β-pNP with its isomers fucosylated at 0-3 or 0-6 of the sugar moiety. The three products were obtained in a ratio of 58: 22 : 20 and in 40.6% overall yield based on the donor added. Replacement of p-nitrophenyl R-D-glucopyranoside by Gal β-pNP resulted in a (1→3) -linked product as the main transfer product along with (1→2) -, (1→4) -, and (1→6) -linked isomers. With p-nitrophenyl β-lactoside acceptor, fucosylation occurred at 0-2', 0-3', and 0-6' of the Gal residue of the acceptor, but the regioselectivity was much lower than that of Gal R-pNP, while the enzyme catalyzed the formation of (1→3) - and (1→4) -linked products with p-nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranoside acceptor.

Journal

  • Journal of Applied Glycoscience

    Journal of Applied Glycoscience 46(3), 241-247, 1999-08-31

    The Japanese Society of Applied Glycoscience

References:  18

Cited by:  1

Codes

  • NII Article ID (NAID)
    10008259141
  • NII NACSIS-CAT ID (NCID)
    AN10453916
  • Text Lang
    ENG
  • Article Type
    Journal Article
  • ISSN
    13403494
  • NDL Article ID
    4846117
  • NDL Source Classification
    ZP24(科学技術--化学・化学工業--糖・澱粉)
  • NDL Call No.
    Z17-15
  • Data Source
    CJP  CJPref  NDL  J-STAGE  JASI 
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