TDP-D-mycaminose

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: TDP-D-mycaminose
• 英文别名: dTDP-alpha-D-mycaminose；[(2R,3R,4S,5S,6R)-4-(dimethylamino)-3,5-dihydroxy-6-methyloxan-2-yl] [hydroxy-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl] hydrogen phosphate
• 化学式: C₁₈H₃₁N₃O₁₄P₂
• 分子量: 575.403
• InChiKey: IJJNPDQFXCRKOA-WHRNYZGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.3
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  234
• 氢给体数：
  6
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  2,4-di-O-acetyl-D-mycaminose 在 palladium on activated charcoal 吡啶 、 四氮唑 、 氢气 、 碳酸氢钠 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， -50.0~20.0 ℃ 、101.33 kPa 条件下， 反应 52.0h， 生成 TDP-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

• Expression, Purification, and Characterization of TylM1, an <i>N</i>,<i>N</i>-Dimethyltransferase Involved in the Biosynthesis of Mycaminose
  作者：Huawei Chen、Zhihong Guo、Hung-wen Liu

  DOI：10.1021/ja9815881

  日期：1998.9.1
• 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.