(S)-10-hydroxy-cis-12-cis-15-octadecadienoic acid | 1400693-84-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-10-hydroxy-cis-12-cis-15-octadecadienoic acid
• CAS: 1400693-84-6
• 化学式: C₁₈H₃₂O₃
• 分子量: 296.45
• InChiKey: WPPBDPYWQAWPCV-LIJKBALDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.86
• 重原子数：
  21.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-10-hydroxy-cis-12-cis-15-octadecadienoic acid 在 conjugated linoleic acid dehydrogenase 、 nicotinamide adenine dinucleotide 、 还原型辅酶Ⅰ 、 bovine serum albumin 作用下， 以 正己烷 为溶剂， 反应 1.0h， 生成 (12Z,15Z)-methyl 10-hydroxyoctadeca-12,15-dienoate
  参考文献：
  名称：

  Characterization of hydroxy fatty acid dehydrogenase involved in polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a

  摘要：

  Hydroxy fatty acid dehydrogenase, which is involved in polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a, was cloned, expressed, purified, and characterized. The enzyme preferentially catalyzed NADH-dependent hydrogenation of oxo fatty acids over NAD(+)-dependent dehydrogenation of hydroxy fatty acids. In the dehydrogenation reaction, fatty acids with an internal hydroxy group such as 10-hydroxy-cis-12-octadecenoic acid, 12-hydroxy-cis-9-octadecenoic acid, and 13-hydroxy-cis-9-octadecenoic acid served as better substrates than those with alpha- or beta-hydroxy groups such as 3-hydroxyoctadecanoic acid or 2-hydroxyeicosanoic acid. The apparent Km value for 10-hydroxy-cis-12-octadecenoic acid (HYA) was estimated to be 38 mu M with a k(cat) of 7.6 x 10(-3) s(-1). The apparent K-m value for 10-oxo-cis-12-octadecenoic acid (KetoA) was estimated to be 1.8 mu M with a k(cat) of 5.7 x 10(-1) s(-1). In the hydrogenation reaction of KetoA, both (R)- and (S)-HYA were generated, indicating that the enzyme has low stereoselectivity. This is the first report of a dehydrogenase with a preference for fatty acids with an internal hydroxy group. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2015.03.020
• 作为产物：
  描述：

  (12Z,15Z)-10-oxooctadeca-12,15-dienoic acid 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 0.5h， 生成 (S)-10-hydroxy-cis-12-cis-15-octadecadienoic acid
  参考文献：
  名称：

  Enantio-selective reduction of the flowering related compound KODA and its analogues in Pharbitis nil cv. Violet

  摘要：

  Plant oxylipins are an important class of signaling molecules in plants. The cyclic adducts of epinephrine or norepinephrine with the naturally occurring oxylipin (12Z,15Z)-9-hydroxy-10-oxo-octadeca-12,15-dienoic acid (KODA, 1) or its synthetic analogues (2-6) have been reported to possess flower-inducing activity toward Lemna paucicostata. By in vivo and in vitro experiments with seedlings of Pharbitis nil cv. Violet carbonyl groups of the alpha-ketols (1 and 3) and the ketones (7 and 9) were enantio-selectively reduced to give their corresponding vicinal diols (2 and 4) and alcohols (8 and 10). The stereochemistry at the oxymethine carbon was determined based on the long range C H coupling constants and the modified Mosher's method. Orientation of the adjacent hydroxyl group in (1 and 3) did not affect the enantio-selectivity, whereas the conversion was slightly affected and higher yields were obtained with the R-enantiomers of the alpha-ketols. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.077

文献信息

• Characterization of hydroxy fatty acid dehydrogenase involved in polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a
  作者：Michiki Takeuchi、Shigenobu Kishino、Si-Bum Park、Nahoko Kitamura、Jun Ogawa

  DOI：10.1016/j.molcatb.2015.03.020

  日期：2015.7

  Hydroxy fatty acid dehydrogenase, which is involved in polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a, was cloned, expressed, purified, and characterized. The enzyme preferentially catalyzed NADH-dependent hydrogenation of oxo fatty acids over NAD(+)-dependent dehydrogenation of hydroxy fatty acids. In the dehydrogenation reaction, fatty acids with an internal hydroxy group such as 10-hydroxy-cis-12-octadecenoic acid, 12-hydroxy-cis-9-octadecenoic acid, and 13-hydroxy-cis-9-octadecenoic acid served as better substrates than those with alpha- or beta-hydroxy groups such as 3-hydroxyoctadecanoic acid or 2-hydroxyeicosanoic acid. The apparent Km value for 10-hydroxy-cis-12-octadecenoic acid (HYA) was estimated to be 38 mu M with a k(cat) of 7.6 x 10(-3) s(-1). The apparent K-m value for 10-oxo-cis-12-octadecenoic acid (KetoA) was estimated to be 1.8 mu M with a k(cat) of 5.7 x 10(-1) s(-1). In the hydrogenation reaction of KetoA, both (R)- and (S)-HYA were generated, indicating that the enzyme has low stereoselectivity. This is the first report of a dehydrogenase with a preference for fatty acids with an internal hydroxy group. (C) 2015 Elsevier B.V. All rights reserved.
• Enantio-selective reduction of the flowering related compound KODA and its analogues in Pharbitis nil cv. Violet
  作者：Ariaki Murata、Kenji Kai、Ken Tsutsui、Jun Takeuchi、Yasushi Todoroki、Kazuo Furihata、Mineyuki Yokoyama、Susanne Baldermann、Naoharu Watanabe

  DOI：10.1016/j.tet.2012.04.077

  日期：2012.7

  Plant oxylipins are an important class of signaling molecules in plants. The cyclic adducts of epinephrine or norepinephrine with the naturally occurring oxylipin (12Z,15Z)-9-hydroxy-10-oxo-octadeca-12,15-dienoic acid (KODA, 1) or its synthetic analogues (2-6) have been reported to possess flower-inducing activity toward Lemna paucicostata. By in vivo and in vitro experiments with seedlings of Pharbitis nil cv. Violet carbonyl groups of the alpha-ketols (1 and 3) and the ketones (7 and 9) were enantio-selectively reduced to give their corresponding vicinal diols (2 and 4) and alcohols (8 and 10). The stereochemistry at the oxymethine carbon was determined based on the long range C H coupling constants and the modified Mosher's method. Orientation of the adjacent hydroxyl group in (1 and 3) did not affect the enantio-selectivity, whereas the conversion was slightly affected and higher yields were obtained with the R-enantiomers of the alpha-ketols. (c) 2012 Elsevier Ltd. All rights reserved.