交沙霉丙酯 | 40922-77-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 交沙霉丙酯
• 中文别名: 无味角沙霉素；丙酸交沙霉素；无味交沙霉素；交沙霉素
• 英文名称: josamycin propionate
• 英文别名: Leucomycin V, 3-acetate 4B-(3-methylbutanoate) 9-propanoate；[(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4-acetyloxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-10-propanoyloxy-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] 3-methylbutanoate
• CAS: 40922-77-8
• 化学式: C₄₅H₇₃NO₁₆
• 分子量: 884.072
• InChiKey: NVBREHSOJSEKBQ-ZQMZUEOGSA-N

物化性质

• 沸点：
  887.2±65.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)
• 溶解度：
  几乎不溶于水，易溶于甲醇和二氯甲烷，溶于丙酮。

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  62
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  212
• 氢给体数：
  2
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  交沙霉丙酯 在 盐酸 作用下， 反应 3.0h， 以67%的产率得到D-mycaminose
  参考文献：
  名称：

  In Vitro Reconstitution of EryCIII Activity for the Preparation of Unnatural Macrolides

  摘要：

  EryCIII is a desosaminyltransferase that converts an inactive macrolide precursor to a biologically active antibiotic. It may have potential for the synthesis of unnatural macrolides with useful biological activities. However, it has been difficult to reconstitute the activity of EryCIII in vitro. We report here that purified, inactive EryCIII can be converted to an active catalyst by the addition of another protein encoded in the same gene cluster, EryCII. The EryCII-treated protein retains activity even when EryCII is removed. We also show that AknT, an activator protein from an unrelated gene cluster, is capable of activating EryCIII. Although the mechanism of activation is not yet understood, we have concluded from these experiments that these antibiotic Gtf activator proteins do not function to deliver substrates to EryCIII and do not exert their effects by forming stable complexes with the Gtf during the glycosyltransfer reaction. We report that activated EryCIII is capable of utilizing an alternative sugar donor, so these results lay the groundwork for the production of novel macrolides.

  DOI：

  10.1021/ja053704n

文献信息

• In Vitro Reconstitution of EryCIII Activity for the Preparation of Unnatural Macrolides
  作者：Yanqiu Yuan、Hak Suk Chung、Catherine Leimkuhler、Christopher T. Walsh、Daniel Kahne、Suzanne Walker

  DOI：10.1021/ja053704n

  日期：2005.10.1

  EryCIII is a desosaminyltransferase that converts an inactive macrolide precursor to a biologically active antibiotic. It may have potential for the synthesis of unnatural macrolides with useful biological activities. However, it has been difficult to reconstitute the activity of EryCIII in vitro. We report here that purified, inactive EryCIII can be converted to an active catalyst by the addition of another protein encoded in the same gene cluster, EryCII. The EryCII-treated protein retains activity even when EryCII is removed. We also show that AknT, an activator protein from an unrelated gene cluster, is capable of activating EryCIII. Although the mechanism of activation is not yet understood, we have concluded from these experiments that these antibiotic Gtf activator proteins do not function to deliver substrates to EryCIII and do not exert their effects by forming stable complexes with the Gtf during the glycosyltransfer reaction. We report that activated EryCIII is capable of utilizing an alternative sugar donor, so these results lay the groundwork for the production of novel macrolides.