hemigossypol-6-methyl ether | 50399-95-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: hemigossypol-6-methyl ether
• 英文别名: 2,8-Dihydroxy-3-methoxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde
• CAS: 50399-95-6
• 化学式: C₁₆H₁₈O₄
• 分子量: 274.317
• InChiKey: XOXRFBVTHNRDNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  hemigossypol-6-methyl ether 在 (+)-gossypol-forming dirigent protein of Gossypium hirsutum var. marie-galante 作用下， 以62.7%的产率得到6,6'-dimethoxy-gossypol
  参考文献：
  名称：

  Stereoselective coupling of hemigossypol to form (+)-gossypol in moco cotton is mediated by a dirigent protein

  摘要：

  The terpenoid gossypol, a secondary metabolite found in the cotton plant, is synthesized by a free radical dimerization of hemigossypol. Gossypol exists as an atropisomeric mixture because of restricted rotation around the central binaphthyl bond. The dimerization of hemigossypol is regiospecific in cotton. In the case of some moco cotton, the dimerization also exhibits a high level of stereoselectivity. The mechanism that controls this stereoselective dimerization is poorly understood. In this paper, we demonstrate that a dirigent protein controls this stereoselective dimerization process. A partially purified protein preparation from cotton flower petals, which by itself is unable to convert hemigossypol to gossypol, converts hemigossypol with a 30% atropisomeric excess into (+)-gossypol when combined with an exogenous laccase, which by itself produces racemic gossypol. Published by Elsevier Ltd.

  DOI：

  10.1016/j.phytochem.2008.06.007

文献信息

• Stereoselective coupling of hemigossypol to form (+)-gossypol in moco cotton is mediated by a dirigent protein
  作者：Jinggao Liu、Robert D. Stipanovic、Alois A. Bell、Lorraine S. Puckhaber、Clint W. Magill

  DOI：10.1016/j.phytochem.2008.06.007

  日期：2008.12

  The terpenoid gossypol, a secondary metabolite found in the cotton plant, is synthesized by a free radical dimerization of hemigossypol. Gossypol exists as an atropisomeric mixture because of restricted rotation around the central binaphthyl bond. The dimerization of hemigossypol is regiospecific in cotton. In the case of some moco cotton, the dimerization also exhibits a high level of stereoselectivity. The mechanism that controls this stereoselective dimerization is poorly understood. In this paper, we demonstrate that a dirigent protein controls this stereoselective dimerization process. A partially purified protein preparation from cotton flower petals, which by itself is unable to convert hemigossypol to gossypol, converts hemigossypol with a 30% atropisomeric excess into (+)-gossypol when combined with an exogenous laccase, which by itself produces racemic gossypol. Published by Elsevier Ltd.

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