N-acetyl-2-deoxy-scyllo-inosamine | 108391-63-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-acetyl-2-deoxy-scyllo-inosamine
• 英文别名: N-[(1S,2R,3S,4S,5R)-2,3,4,5-tetrahydroxycyclohexyl]acetamide
• CAS: 108391-63-5
• 化学式: C₈H₁₅NO₅
• 分子量: 205.211
• InChiKey: JYCMXSZAVKHPJV-SHGPDSBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-acetyl-2-deoxy-scyllo-inosamine 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 32.0h， 生成 N-acetyl-N-benzoyl-3,4,5,6-tetra-O-benzoyl-2-deoxy-scyllo-inosamine
  参考文献：
  名称：

  Stereochemical Recognition of Doubly Functional Aminotransferase in 2-Deoxystreptamine Biosynthesis

  摘要：

  The doubly functional aminotransferase BtrS in the 2-deoxystreptamine (DOS) biosynthesis, in which two transaminations are involved, was characterized by a genetic as well as a chemical approach with the heterologously expressed enzyme. The gene disruption study clearly showed that BtrS is involved, in addition to the previously confirmed first transamination, in the second transamination as well. This dual function of BtrS for the DOS biosynthesis was further confirmed by the structural determination of the reverse reaction product from DOS. Enantiospecific formation of the reverse reaction product from DOS clearly showed that BtrS distinguishes the enantiotopic amino groups of DOS, but in contrast, both enantiomers of 2-deoxy-scyllo-inosose (DOI) were efficiently accepted by BtrS to give a racemic product. This unique stereochemical recognition of DOI chirality and DOS prochirality by BtrS is mechanistically explained by a specific hydrogen-bond donating force in the enzyme active site as a particular feature of this doubly functional enzyme.

  DOI：

  10.1021/ja0445948
• 作为产物：
  描述：

  (3R,4R,5R)-5-(2-Nitro-ethyl)-tetrahydro-furan-2,3,4-triol 在 platinum(IV) oxide barium dihydroxide 、 氢气 作用下， 以 水 为溶剂， 反应 30.08h， 生成 N-acetyl-2-deoxy-scyllo-inosamine
  参考文献：
  名称：

  3-氨基-2,3-二脱氧-D-肌醇（2-脱氧链胺生物合成的中间体）及其D-表位立体异构体的化学合成。

  摘要：

  DOI：

  10.1016/s0008-6215(00)90119-8