Synthesis of Novel Thioglycoside Analogs as the Substrates and/or the Inhibitors of Cellobiohydrolases

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A series of β-(1→4)-thiooligosaccharide analogs, <I>O</I>-β-D-glucopyranosyl-(1→4)-<I>S</I>-β-D- glucopyranosyl-(1→4)-4-deoxy-4-thio-D-glucopyranose (<B>1</B>: Glc-<I>O</I>-Glc-<I>S</I>-Glc), <I>S</I>-β-D-glucopyranosyl- (1→4)-<I>O</I>-(4-deoxy-4-thio-β-D-glucopyranosyl)-(1→4)-D-glucopyranose (<B>2</B>: Glc-<I>S</I>-Glc-<I>O</I>-Glc), <I>S</I>-β-D-glucopyranosyl-(1→4)-4-deoxy-4-thio-D-glucopyranose (<B>3</B>: Glc-<I>S</I>-Glc), <I>O</I>-β-D-galactopyranosyl-(1→4)-<I>S</I>-β-D-glucopyranosyl-(1→4)-4-deoxy-4-thio-D-glucopyranose (<B>4</B>: Gal-<I>O</I>-Glc-<I>S</I>-Glc) and <I>O</I>-β-D-glucopyranosyl-(1→4)-<I>S</I>-β-D-glucopyranosyl-(1→4)-<I>O</I>- (4-deoxy-4-thio-β-D-glucopyranosyl)-(1→4)-D-glucopyranose (<B>5</B>: Glc-<I>O</I>-Glc-<I>S</I>-Glc-<I>O</I>-Glc), including novel compounds were synthesized for the substrates and/or the inhibitors of cellobiohydrolases for the evaluation of cellulolytic activities. The triflated acceptors were constructed in two reaction steps, regioselective benzoylation and triflation. After <I>S</I>-glycosylation of these triflated acceptors, acyl protecting group was deprotected to yield target compounds. In this way, all target compounds were successfully synthesized in short-step (four reaction steps).

収録刊行物

  • Journal of applied glycoscience

    Journal of applied glycoscience 59(1), 11-19, 2012-02-20

    日本応用糖質科学会

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各種コード

  • NII論文ID(NAID)
    10030138276
  • NII書誌ID(NCID)
    AA11809133
  • 本文言語コード
    ENG
  • 資料種別
    ART
  • ISSN
    13447882
  • NDL 記事登録ID
    023566975
  • NDL 請求記号
    Z78-A693
  • データ提供元
    CJP書誌  NDL  J-STAGE 
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