5-[(2E)-3,7-dimethylocta-2,6-dienyl]naphthalene-1,6-diol | 862162-16-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-[(2E)-3,7-dimethylocta-2,6-dienyl]naphthalene-1,6-diol
• CAS: 862162-16-1
• 化学式: C₂₀H₂₄O₂
• 分子量: 296.409
• InChiKey: GQFQSMHTXCVPJC-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  香叶基焦磷酸铵盐 、 1,6-二羟基萘 在 Tris-HCl buffer 、 magnesium chloride 作用下， 生成 2-[(2E)-3,7-dimethylocta-2,6-dienyl]naphthalene-1,6-diol 、 (E)-4-(3,7-dimethylocta-2,6-dien-1-yl)naphthalene-1,6-diol 、 5-[(2E)-3,7-dimethylocta-2,6-dienyl]naphthalene-1,6-diol
  参考文献：
  名称：

  Chemoenzymatic syntheses of prenylated aromatic small molecules using Streptomyces prenyltransferases with relaxed substrate specificities

  摘要：

  NphB is a soluble prenyltransferase from Streptomyces sp. strain CL190 that attaches a geranyl group to a 1,3,6,8-tetrahydroxynaphthalene-derived polyketide during the biosynthesis of anti-oxidant naphterpin. Here we report multiple chemoenzymatic syntheses of various prenylated compounds from aromatic substrates including flavonoids using two prenyltransferases NphB and SCO7190, a NphB homolog from Streptomyces coelicolor A3( 2), as biocatalysts. NphB catalyzes carbon-carbon-based and carbon-oxygen-based geranylation of a diverse collection of hydroxyl-containing aromatic acceptors. Thus, this simple method using the prenyltransferases can be used to explore novel prenylated aromatic compounds with biological activities. Kinetic studies with NphB reveal that the prenylation reaction follows a sequential ordered mechanism. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.052

文献信息

• Chemoenzymatic syntheses of prenylated aromatic small molecules using Streptomyces prenyltransferases with relaxed substrate specificities
  作者：Takuto Kumano、Stéphane B. Richard、Joseph P. Noel、Makoto Nishiyama、Tomohisa Kuzuyama

  DOI：10.1016/j.bmc.2008.07.052

  日期：2008.9

  NphB is a soluble prenyltransferase from Streptomyces sp. strain CL190 that attaches a geranyl group to a 1,3,6,8-tetrahydroxynaphthalene-derived polyketide during the biosynthesis of anti-oxidant naphterpin. Here we report multiple chemoenzymatic syntheses of various prenylated compounds from aromatic substrates including flavonoids using two prenyltransferases NphB and SCO7190, a NphB homolog from Streptomyces coelicolor A3( 2), as biocatalysts. NphB catalyzes carbon-carbon-based and carbon-oxygen-based geranylation of a diverse collection of hydroxyl-containing aromatic acceptors. Thus, this simple method using the prenyltransferases can be used to explore novel prenylated aromatic compounds with biological activities. Kinetic studies with NphB reveal that the prenylation reaction follows a sequential ordered mechanism. (C) 2008 Elsevier Ltd. All rights reserved.