13-hydroxynootkatone | 141695-86-5

• 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: 13-hydroxynootkatone
• 英文别名: 12-hydroxynootkatone；(+)-(4R,5S,7R)-13-hydroxynootkatone；(4R,4aS,6R)-6-(3-hydroxyprop-1-en-2-yl)-4,4a-dimethyl-3,4,5,6,7,8-hexahydronaphthalen-2-one
• CAS: 141695-86-5
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: AZDUDOOVVZKDCK-JMSVASOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (+)-香柏酮 在 5-氨基乙酰丙酸 、 异丙基-beta-D-硫代半乳糖吡喃糖苷 作用下， 以 aq. phosphate buffer 为溶剂， 反应 24.0h， 生成 13-hydroxynootkatone
  参考文献：
  名称：

  棉铃虫中CYP260A1和CYP264B1的新倍半萜烯氧化

  摘要：

  用于精确氧化的P450：这项工作比较了细菌CYP260A1和CYP264B1对四种倍半萜烯底物氧化的特异性和区域选择性。使用基于大肠杆菌的全细胞转化系统。填补了细菌P450催化的倍半萜烯氧化的空白，我们获得了以前的萜类P450转化研究中未观察到的产物。

  DOI：

  10.1002/cbic.201500417

文献信息

• New Sesquiterpene Oxidations with CYP260A1 and CYP264B1 from<i>Sorangium cellulosum</i>So ce56
  作者：Alexander Schifrin、Martin Litzenburger、Michael Ringle、Thuy T. B. Ly、Rita Bernhardt

  DOI：10.1002/cbic.201500417

  日期：2015.12

  P450s for precision oxidation: This work compares the specificities and regioselectivities of the bacterial CYP260A1 and CYP264B1 for the oxidation of four sesquiterpene substrate classes. A whole‐cell conversion system based on E. coli was employed. Filling gaps in sesquiterpene oxidations catalyzed by bacterial P450s, we obtained products that had not been observed in previous P450 conversion studies

  用于精确氧化的P450：这项工作比较了细菌CYP260A1和CYP264B1对四种倍半萜烯底物氧化的特异性和区域选择性。使用基于大肠杆菌的全细胞转化系统。填补了细菌P450催化的倍半萜烯氧化的空白，我们获得了以前的萜类P450转化研究中未观察到的产物。
• Natural Product Diversification by One‐Step Biocatalysis using Human P450 3A4
  作者：Nico D. Fessner、Christopher Grimm、Matic Srdič、Hansjörg Weber、Wolfgang Kroutil、Ulrich Schwaneberg、Anton Glieder

  DOI：10.1002/cctc.202101564

  日期：2022.1.10

  Doing it all: In this study, the synthetic potential of human cytochrome P450 3A4 as a Pichia pastoris-based whole-cell biocatalyst for the diversification of natural products was successfully explored. A total of 31 authentic human metabolites of six selected natural products were isolated at a preparative 100-mg scale, many of them for the first time, revealing an unprecedented degree of diversification

  全力以赴：在这项研究中，成功​​探索了人类细胞色素 P450 3A4 作为基于毕赤酵母的全细胞生物催化剂在天然产物多样化方面的合成潜力。以 100 mg 的制备规模分离了六种选定天然产物的总共 31 种真实人体代谢物，其中许多是第一次，揭示了前所未有的多样化程度。
• Enhancing the Efficiency and Regioselectivity of P450 Oxidation Catalysts by Unnatural Amino Acid Mutagenesis
  作者：Joshua N. Kolev、Jacqueline M. Zaengle、Rajesh Ravikumar、Rudi Fasan

  DOI：10.1002/cbic.201400060

  日期：2014.5.5

  Unnatural choice: Incorporating unnatural amino acids at single positions within the active site of a cytochrome P450 significantly changes the regioselectivity (shown) of the enzyme or enhances its catalytic efficiency. This study demonstrates that unnatural amino acid mutagenesis constitutes a promising new strategy for improving P450 oxidation catalysts.

  非天然选择：在细胞色素 P450 活性位点内的单个位置加入非天然氨基酸显着改变酶的区域选择性（如图所示）或提高其催化效率。该研究表明，非天然氨基酸诱变构成了改进 P450 氧化催化剂的有前途的新策略。
• Microbial transformation of (+)-nootkatone and the antiproliferative activity of its metabolites
  作者：Anna Gliszczyńska、Agnieszka Łysek、Tomasz Janeczko、Marta Świtalska、Joanna Wietrzyk、Czesław Wawrzeńczyk

  DOI：10.1016/j.bmc.2011.01.062

  日期：2011.4

  Six metabolites were obtained as a result of microbial transformation of (+)-nootkatone (1) by the fungal strains: Botrytis, Didymosphaeria, Aspergillus, Chaetomium and Fusarium. Their structure were established as (+)-(4R,5S,7R,9R)-9 alpha-hydroxynootkatone (2), (+)-(4R,5S,7R)-13-hydroxynootkatone (3) and (+)(4R,5S,7R,9R,11S)-11,12-epoxy-9 alpha-hydroxynootkatone (4), (+)-(4R,5S,7R,11S)-11,12-epoksynootkatone (5), (+)-(4R,5S,7R)-11,12-dihydroxynootkatone (6) and (+)-(4R, 5S, 7R)-7,11,12-trihydroxynootkatone (7) on the basis of their spectral data. Two products: (4) and (7) were not previously reported in the literature. The antiproliferative activity of (+)-nootkatone (1) and isolated metabolites (2-7) of its biotransformation has been evaluated. (C) 2011 Elsevier Ltd. All rights reserved.
• Tateba, Hideki; Morita, Kouzou; Tada, Masahiro, Journal of Chemical Research, Miniprint, 1992, # 5, p. 1001 - 1024
  作者：Tateba, Hideki、Morita, Kouzou、Tada, Masahiro

  DOI：——

  日期：——