| 1394301-47-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1394301-47-3
• 化学式: C₂₇H₃₀O₅
• 分子量: 434.532
• InChiKey: KXRXEZHORZBFII-KWXIBIRDSA-N

物化性质

• 沸点：
  566.4±50.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  32.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 吡啶 、 四氮唑 、 三甲基溴硅烷 、 四溴化碳 、 10% Pd/C 、 20% Pd(OH)2/C 、 氢气 、 三苯基膦 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 119.0h， 生成
  参考文献：
  名称：

  Analysis of UDP-d-Apiose/UDP-d-Xylose Synthase-Catalyzed Conversion of UDP-d-Apiose Phosphonate to UDP-d-Xylose Phosphonate: Implications for a Retroaldol–Aldol Mechanism

  摘要：

  UDP-D-apiose/UDP-D-xylose synthase (AXS) catalyzes the conversion of UDP-D-glucuronic acid to UDP-D-apiose and UDP-D-xylose. An acetyl-protected phosphonate analogue of UDP-D-apiose was synthesized and used in an in situ HPLC assay to demonstrate for the first time the ability of AXS to interconvert the two reaction products. Density functional theory calculations provided insight into the energetics of this process and the apparent inability of AXS to catalyze the conversion of UDP-D-xylose to UDP-D-apiose. The data suggest that this observation is unlikely to be due to an unfavorable equilibrium but rather results from substrate inhibition by the most stable chair conformation of UDP-D-xylose. The detection of xylose cyclic phosphonate as the turnover product reveals significant new details about the AXS-catalyzed reaction and supports the proposed retroaldol-aldol mechanism of catalysis.

  DOI：

  10.1021/ja305322x
• 作为产物：
  描述：

  在 正丁基锂 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 17.75h， 生成
  参考文献：
  名称：

  Analysis of UDP-d-Apiose/UDP-d-Xylose Synthase-Catalyzed Conversion of UDP-d-Apiose Phosphonate to UDP-d-Xylose Phosphonate: Implications for a Retroaldol–Aldol Mechanism

  摘要：

  UDP-D-apiose/UDP-D-xylose synthase (AXS) catalyzes the conversion of UDP-D-glucuronic acid to UDP-D-apiose and UDP-D-xylose. An acetyl-protected phosphonate analogue of UDP-D-apiose was synthesized and used in an in situ HPLC assay to demonstrate for the first time the ability of AXS to interconvert the two reaction products. Density functional theory calculations provided insight into the energetics of this process and the apparent inability of AXS to catalyze the conversion of UDP-D-xylose to UDP-D-apiose. The data suggest that this observation is unlikely to be due to an unfavorable equilibrium but rather results from substrate inhibition by the most stable chair conformation of UDP-D-xylose. The detection of xylose cyclic phosphonate as the turnover product reveals significant new details about the AXS-catalyzed reaction and supports the proposed retroaldol-aldol mechanism of catalysis.

  DOI：

  10.1021/ja305322x