プリメベロースとその配糖体の実践的酵素合成 Practical Enzymatic Synthesis of Primeverose and Its Glycoside

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Author(s)

    • 村田 健臣 MURATA Takeomi
    • 静岡大学農学部応用生物化学科 Department of Applied Biological Chemistry, Faculty of Agriculture, Shizuoka University
    • 島田 睦 SHIMADA Mutsumi
    • 静岡大学農学部応用生物化学科 Department of Applied Biological Chemistry, Faculty of Agriculture, Shizuoka University
    • 坂田 完三 SAKATA Kanzo
    • 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

Aspergillus puiverulentus由来のβ-キシロシターゼは,4-O-β-D-キシロピラノシル-D-キシロピラノース(キシロビオース)からD-グルコースの1級水酸基への高位置選択的キシロシル移転反応を触媒し,6-O-β-D-キシロピラノシル-D-グルコピラノース(プリメベロース,1)を生成した.本2糖は活性炭-セライトカラムクロマトグラフィーにより29%の収率で容易に単離できた.同様にして,D-グルコースの代わりに<I>p</I>-ニトロフェニルβ-D-グルコピラノシドを受容体基質として用いた場合,本酵素によって<I>p</I>-ニトロフェニル6-O-β-D-キシロピラノシル-β-D-グルコピラノシド(<I>p</I>NPβ-プリメベロシド,2)が優先的に生成し,その構造異性体である<I>p</I>NP4-O-β-D-キシロピラノシル-β-D-グルコピラノシドと<I>p</I>NP3-O-β-D-キシロピラノシル-β-D-グルコピラノシドも同時に生成した.3種類の転移生成物はトヨパールHW-40Sカラムクロマトグラフィーによって容易に分離され,目的化合物2を受容体基質当り13%の収率で得た.これらの糖転移反応は,1および2のワンポット合成法として有効であった.

β-D-Xylosidase from Aspergillus pulverulentus regioselectively induced a β-D-xylosyl transfer reac-tion from 4-0-β-D-xylopyranosyl-D-xylopyranose (xylobiose) to the primary hydroxyl group of D-glucose. The 6-0-β-D-xylopyranosyl-β-D-glucopyranose (primeverose, 1) produced was isolated by chromatography on a column of charcoal-Celite in a 29% overall yield based on the donor. In the same way, when p-nitrophenyl β-D-glucopyranoside was used as an acceptor instead of D-glucose, the enzyme predominated p-nitrophenyl 6-0-β-D-xylopyranosyl-β-D-glucopyranoside (pNP β-primeveroside, 2) to its isomers, pNP 4-0-β-D-xylopyranosyl-β-D-glucopyranoside and pNP 3-O-β-D-xylopyranosyl-β-D-glucopyranoside. Three transfer products were easily separated from one another by Toyopearl HW-40S column chromatography and the desired compound, 2, was obtained in a 13% yield based on the acceptor added. These reactions were efficient enough. to allow one-pot preparations of 1 and 2.

Journal

  • Journal of Applied Glycoscience

    Journal of Applied Glycoscience 46(4), 431-437, 1999-12-01

    The Japanese Society of Applied Glycoscience

References:  22

Cited by:  3

Codes

  • NII Article ID (NAID)
    10008259417
  • NII NACSIS-CAT ID (NCID)
    AN10453916
  • Text Lang
    ENG
  • Article Type
    Journal Article
  • ISSN
    13403494
  • NDL Article ID
    4976608
  • 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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