(-)-(4R,5S)-4,5,7-trihydroxy-2-methylidene-6-oxo-heptanenitrile | 681826-38-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(4R,5S)-4,5,7-trihydroxy-2-methylidene-6-oxo-heptanenitrile
• 英文别名: (4R,5S)-4,5,7-trihydroxy-2-methylidene-6-oxoheptanenitrile
• CAS: 681826-38-0
• 化学式: C₈H₁₁NO₄
• 分子量: 185.18
• InChiKey: OKEYZYDECWWZDQ-SVRRBLITSA-N

物化性质

• 沸点：
  493.4±45.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-(4R,5S)-4,5,7-trihydroxy-2-methylidene-6-oxo-heptanenitrile 在 formate dehydrogenase (E_.C_. 1.2.1.2) 、 L-sorbitol dehydrogenase (E_.C_. 1.1.1.14) 、 sodium formate 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 phosphate buffer 为溶剂， 反应 1.0h， 生成 (+)-(4R,5S,6S)-4,5,6,7-tetrakis-benzyloxy-2-methylidene-heptanenitrile
  参考文献：
  名称：

  Transketolase and fructose-1,6-bis-phosphate aldolase, complementary tools for access to new ulosonic acid analogues

  摘要：

  A new approach to the synthesis of ulosonic acids KDO and DAH is described. The key step is the C-5-C-6 bond formation catalysed by fructose-1,6-bisphosphate aldolase (for KDO) or transketolase (for DAH) using substituted acrylonitrile alpha-hydroxyaldehyde. All asymmetric carbon configurations are determined in an enzymatic step by the means of deshydrogenase or lipase. This strategy, using a non-metabolism pathway, allows access to novel precursors of KDO, DAH and analogues. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.12.069
• 作为产物：
  描述：

  (R)-(+)-5,5-dimethoxy-4-hydroxy-2-methylidene-pentanenitrile 在 thiamine pyrophosphate 、 Dowex 50W-X₈ (H⁽¹⁺⁾-form) 、 transketolase from S_. cerevisiae 、 magnesium chloride 作用下， 以 水 为溶剂， 反应 26.0h， 生成 (-)-(4R,5S)-4,5,7-trihydroxy-2-methylidene-6-oxo-heptanenitrile
  参考文献：
  名称：

  Transketolase and fructose-1,6-bis-phosphate aldolase, complementary tools for access to new ulosonic acid analogues

  摘要：

  A new approach to the synthesis of ulosonic acids KDO and DAH is described. The key step is the C-5-C-6 bond formation catalysed by fructose-1,6-bisphosphate aldolase (for KDO) or transketolase (for DAH) using substituted acrylonitrile alpha-hydroxyaldehyde. All asymmetric carbon configurations are determined in an enzymatic step by the means of deshydrogenase or lipase. This strategy, using a non-metabolism pathway, allows access to novel precursors of KDO, DAH and analogues. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.12.069

文献信息

• Transketolase and fructose-1,6-bis-phosphate aldolase, complementary tools for access to new ulosonic acid analogues
  作者：Dominique Crestia、Colette Demuynck、Jean Bolte

  DOI：10.1016/j.tet.2003.12.069

  日期：2004.3

  A new approach to the synthesis of ulosonic acids KDO and DAH is described. The key step is the C-5-C-6 bond formation catalysed by fructose-1,6-bisphosphate aldolase (for KDO) or transketolase (for DAH) using substituted acrylonitrile alpha-hydroxyaldehyde. All asymmetric carbon configurations are determined in an enzymatic step by the means of deshydrogenase or lipase. This strategy, using a non-metabolism pathway, allows access to novel precursors of KDO, DAH and analogues. (C) 2004 Elsevier Ltd. All rights reserved.