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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (04): 657-662. 上一篇    下一篇

研究论文

两个埃博霉素生物合成中间体修饰化合物的合成

孙鹤a，胡玮a，王纵横a，李越中*,a
赵桂龙b，王建武*,b   

  1. (a State Key Laboratory of Microbial Technology, College of Life Science, Shandong Univer-sity, Jinan 250100)
    (b School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100)
  • 收稿日期:2007-05-28 修回日期:2007-09-01 发布日期:2008-04-17
  • 通讯作者: 王建武

Synthesis of Two Modified Intermediates in Epothilone Biosynthesis

SUN Hea,HU Weia,WANG Zong-Henga,LI Yue-Zhong*,a
ZHAO Gui-Longb,WANG Jian-Wu*,b   

  • Received:2007-05-28 Revised:2007-09-01 Published:2008-04-17
  • Contact: WANG Jian-Wu

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1631

被引次数

21

为了使用前体定向生物合成技术研究埃博霉素的生物合成过程并对其进行分子改造, 选定了两个中间体修饰化合物2-甲基噻唑-4-羧酸2-乙酰氨基乙硫基硫酯和(E)-2-甲基-3-(2-甲基噻唑-4-基)丙烯酸2-乙酰氨基乙硫基硫酯进行了化学全合成的研究. 合成方法比已有的合成方法更易操作, 经济性更好. 所有化合物经红外光谱、质谱、核磁共振谱及元素分析确证了结构.

关键词: 埃博霉素, 2-乙酰氨基乙硫基硫酯, 修饰中间体

In order to investigate the biosynthesis of epothilones and generate novel biosynthetic epothilone analogues by a precursor-directed biosynthesis, two modified intermediates for epothilone biosynthesis were designed and synthesized, which were (2-methylthiazol-4-yl)carboxylic 2-acetamidoethylthiol thioester and (E)-2-methyl-3-(2-methyl-4-thiazoly)acrylic 2-acetamidoethylthiol thioester. The new synthetic procedures utilized were more inexpensive and convenient, and the structures of these compounds were confirmed by IR, MS, 1H NMR and 13C NMR spectra and elemental analysis.

Key words: 2-acetamidoethylthiol thioester, epothilone, modified intermediate