α-D-mycaminosyl phosphate | 765268-76-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-D-mycaminosyl phosphate
• 英文别名: [(2R,3R,4S,5S,6R)-4-(dimethylamino)-3,5-dihydroxy-6-methyloxan-2-yl] dihydrogen phosphate
• CAS: 765268-76-6
• 化学式: C₈H₁₈NO₇P
• 分子量: 271.207
• InChiKey: UMHKRBKNXOMYGH-OZRXBMAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  120
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  α-D-mycaminosyl phosphate 、 O^5'-(hydroxy-morpholin-4-yl-phosphinoyl)-thymidine 在 吡啶 、 四氮唑 作用下， 反应 48.0h， 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
• 作为产物：
  描述：

  Acetic acid (2R,3R,4S,5S,6R)-5-acetoxy-4-dimethylamino-6-methyl-2-phosphonooxy-tetrahydro-pyran-3-yl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 α-D-mycaminosyl phosphate
  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