pentalenic acid | 69394-19-0

• 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: pentalenic acid
• 英文别名: (1S,2R,5R,8S,9R)-9-hydroxy-2,10,10-trimethyltricyclo[6.3.0.01,5]undec-6-ene-6-carboxylic acid
• CAS: 69394-19-0
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: WBLTVUMJMJIOGQ-YCGCYHNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  pentalenic acid 、 三甲基硅烷化重氮甲烷 以 甲醇 、 苯 为溶剂， 反应 0.25h， 生成 pentalenic acid methyl ester
  参考文献：
  名称：

  Pentalenic acid is a shunt metabolite in the biosynthesis of the pentalenolactone family of metabolites: hydroxylation of 1-deoxypentalenic acid mediated by CYP105D7 (SAV_7469) of Streptomyces avermitilis

  摘要：

  反应。

  DOI：

  10.1038/ja.2010.135
• 作为产物：
  描述：

  1-deoxypentalenic acid 在 D-葡萄糖-6-磷酸 、 C-terminal His₄-tagged Streptomyces avermitilis cytochrome P₄₅₀ 105D₇ 、 glucose-6-phodphate dehydrogenase 、 ferredoxin---NADP+ reductase 、 烟酰胺腺嘌呤双核苷酸磷酸盐 、 spinach ferredoxin 作用下， 以 水 、 二甲基亚砜 、 甘油 为溶剂， 反应 2.0h， 生成 pentalenic acid
  参考文献：
  名称：

  Pentalenic acid is a shunt metabolite in the biosynthesis of the pentalenolactone family of metabolites: hydroxylation of 1-deoxypentalenic acid mediated by CYP105D7 (SAV_7469) of Streptomyces avermitilis

  摘要：

  反应。

  DOI：

  10.1038/ja.2010.135

文献信息

• Pentalenic acid is a shunt metabolite in the biosynthesis of the pentalenolactone family of metabolites: hydroxylation of 1-deoxypentalenic acid mediated by CYP105D7 (SAV_7469) of Streptomyces avermitilis
  作者：Satoshi Takamatsu、Lian-Hua Xu、Shinya Fushinobu、Hirofumi Shoun、Mamoru Komatsu、David E Cane、Haruo Ikeda

  DOI：10.1038/ja.2010.135

  日期：2011.1

  Pentalenic acid (1) has been isolated from many Streptomyces sp. as a co-metabolite of the sesquiterpenoid antibiotic pentalenolactone and related natural products. We have previously reported the identification of a 13.4-kb gene cluster in the genome of Streptomyces avermitilis implicated in the biosynthesis of the pentalenolactone family of metabolites consisting of 13 open reading frames. Detailed molecular genetic and biochemical studies have revealed that at least seven genes are involved in the biosynthesis of the newly discovered metabolites, neopentalenoketolactone, but no gene specifically dedicated to the formation of pentalenic acid (1) was evident in the same gene cluster. The wild-type strain of S. avermitilis, as well as its derivatives, mainly produce pentalenic acid (1), together with neopentalenoketolactone (9). Disruption of the sav7469 gene encoding a cytochrome P450 (CYP105D7), members of which class are associated with the hydroxylation of many structurally different compounds, abolished the production of pentalenic acid (1). The sav7469-deletion mutant derived from SUKA11 carrying pKU462∷ ptl-cluster Δ ptlH accumulated 1-deoxypentalenic acid (5), but not pentalenic acid (1). Reintroduction of an extra-copy of the sav7469 gene to SUKA11 Δ sav7469 carrying pKU462∷ ptl-cluster Δ ptlH restored the production of pentalenic acid (1). Recombinant CYP105D7 prepared from Escherichia coli catalyzed the oxidative conversion of 1-deoxypentalenic acid (5) to pentalenic acid (1) in the presence of the electron-transport partners, ferredoxin (Fdx) and Fdx reductase, both in vivo and in vitro. These results unambiguously demonstrate that CYP105D7 is responsible for the conversion of 1-deoxypentalenic acid (5) to pentalenic acid (1), a shunt product in the biosynthesis of the pentalenolactone family of metabolites.

  反应。