6-endo-hydroxycamphor | 3004-27-1

• 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: 6-endo-hydroxycamphor
• 英文别名: 6-endo-Hydroxy-campher；Bicyclo[2.2.1]heptan-2-one, 6-hydroxy-1,7,7-trimethyl-, (1R-endo)-；(1R,4S,6S)-6-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
• CAS: 3004-27-1
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: UNOCSJVDJYDPTN-MHYGZLNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  左旋樟脑 在 putidaredoxin reductase 、 cytochrome P₄₅₀ N₂₄₂A mutant 、 potassium chloride 、 氧气 、 还原型辅酶II(NADPH)四钠盐 、 bovine liver catalase 、 putidaredoxin 作用下， 以 乙醇 为溶剂， 生成 (-)-(1S,4S,5R)-5-endo-hydroxycamphor 、 1,7,7-trimethyl-3-hydroxybicyclo[2.2.1]-heptan-2-one 、 6-endo-hydroxycamphor 、 5-exo-Hydroxy-(+/-)-Camphor
  参考文献：
  名称：

  In vivo and in vitro hydroxylation of cineole and camphor by cytochromes P450CYP101A1, CYP101B1 and N242A CYP176A1

  摘要：

  Cytochromes P450 (P450s) are valuable enzymes that can generate a range of useful compounds via biocatalytic oxidations that complement traditional synthetic chemistry. In this study three bacterial P450s, qP450(cam) (CYP101A1), CYP101B1 and the mutant N242A-P450(cin) (N242A-CYP176A1), were used to produce a range of products from the oxidation of the monoterpenes (1R)- and (1S) -camphor and 1,8-cineole. We demonstrate that both in vitro and in vivo catalytic turnover with these P450s can produce a complement of up to seven hydroxycamphors and seven hydroxycineoles, in addition to compounds produced from further oxidation. The CYP101B1 whole cell catalytic system was found to produce 300-600 mg/L of culture of oxidation products that could be easily separated chromatographically. The CYP101B1 in vitro oxidation of 1,8-cineole primarily produced (1S)-5 alpha-hydroxycineole, which was 78% of the total product formed. However, the amount of (1S)-5a-hydroxycineole was reduced to 42% of the total products when isolated from the CYP101B1 whole cell system. (1S)-6 alpha-Hydroxycineole (96% ee) could be isolated from a whole cell catalytic turnover of 1,8-cineole by N242A-P450c,n in a yield of 46 mg/L (98% of the total product). However, the amount of product isolated ((1R)-5-endo-hydroxycamphor, 75% of the total products) from the whole cell catalytic oxidation of (1R) -camphor with N242A-P450c,n was much lower (6 mg/L) due to the inefficient use of reducing equivalents (3.5 + 0.5%) for substrate oxidation. These compounds will assist in the identification of specific structures in mechanistic investigations and structure elucidation, but further optimisation is required to generate larger quantities for synthetic applications. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2016.03.004