17-hydroxylinoleic acid | 4546-58-1

• 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: 17-hydroxylinoleic acid
• 英文别名: 17-HODE；17-Hydroxylinoleic acid；(9Z,12Z)-17-hydroxyoctadeca-9,12-dienoic acid
• CAS: 4546-58-1
• 化学式: C₁₈H₃₂O₃
• 分子量: 296.45
• InChiKey: PLKBLKWFUGXKDQ-YXRHTCTQSA-N

物化性质

• 沸点：
  422.0±33.0 °C(Predicted)
• 密度：
  0.970±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 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：

  L-glutamine-p-nitrobenzyl ester 、 17-hydroxylinoleic acid 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-(17-hydroxylinoleoyl)-p-nitrobenzyl-glutamine
  参考文献：
  名称：

  摘要：

  Oral secretion of beet armyworm caterpillars (BAW), when applied to damaged tissues of corn seedlings, induces the seedlings to emit volatile compounds that attract the natural enemies of the caterpillars. The key elicitor present in BAW oral secretions is N-[17-hydroxylinolenoyl]-L-glutamine (volicitin). Analysis of the oral secretion showed that it also contained N-[17-hydroxyolinoleoyl]-L-glutamine, free 17-hydroxylinolenic, and 17-hydroxylinoleic acid, the glutamine conjugates of linolenic and linoleic acid as well as free linolenic and linoleic acid. Here we present the identification and synthesis of the hydroxy acids and of glutamine conjugates.

  DOI：

  10.1023/a:1005401814122
• 作为产物：
  描述：

  2-(3-溴丙基)-2-甲基-1,3-二氧戊环 在 P-2 nickel chromium(VI) oxide 、 盐酸 、 N,N-二甲基丙烯基脲 、 sodium tetrahydroborate 、 硫酸 、 乙基溴化镁 、 氢气 、 copper(l) chloride 作用下， 以 四氢呋喃 、 乙醇 、 丙酮 为溶剂， 反应 16.5h， 生成 17-hydroxylinoleic acid
  参考文献：
  名称：

  摘要：

  Oral secretion of beet armyworm caterpillars (BAW), when applied to damaged tissues of corn seedlings, induces the seedlings to emit volatile compounds that attract the natural enemies of the caterpillars. The key elicitor present in BAW oral secretions is N-[17-hydroxylinolenoyl]-L-glutamine (volicitin). Analysis of the oral secretion showed that it also contained N-[17-hydroxyolinoleoyl]-L-glutamine, free 17-hydroxylinolenic, and 17-hydroxylinoleic acid, the glutamine conjugates of linolenic and linoleic acid as well as free linolenic and linoleic acid. Here we present the identification and synthesis of the hydroxy acids and of glutamine conjugates.

  DOI：

  10.1023/a:1005401814122

文献信息

• Selective and Sustainable Production of Sub‐terminal Hydroxy Fatty Acids by a Self‐Sufficient CYP102 Enzyme from <i>Bacillus Amyloliquefaciens</i>
  作者：Li Zong、Yan Zhang、Zhengkang Shao、Anita Ljubic、Charlotte Jacobsen、Renjun Gao、Bekir Engin Eser、Yingwu Wang、Zheng Guo

  DOI：10.1002/cbic.202300368

  日期：2023.9.15

  Enzymatic hydroxylation of fatty acids by Cytochrome P450s (CYPs) offers an eco‐friendly route to hydroxy fatty acids (HFAs), high‐value oleochemicals with various applications in materials industry and with potential as bioactive compounds. However, instability and poor regioselectivity of CYPs are their main drawbacks. A newly discovered self‐sufficient CYP102 enzyme, BAMF0695 from Bacillus amyloliquefaciens DSM 7, exhibits preference for hydroxylation of sub‐terminal positions (ω‐1, ω‐2, and ω‐3) of fatty acids. Our studies show that BAMF0695 has a broad temperature optimum (over 70 % of maximal enzymatic activity retained between 20 to 50 °C) and is highly thermostable (T₅₀ >50 °C), affording excellent adaptive compatibility for bioprocesses. We further demonstrate that BAMF0695 can utilize renewable microalgae lipid as a substrate feedstock for HFA production. Moreover, through extensive site‐directed and site‐saturation mutagenesis, we isolated variants with high regioselectivity, a rare property for CYPs that usually generate complex regioisomer mixtures. BAMF0695 mutants were able to generate a single HFA regiosiomer (ω‐1 or ω‐2) with selectivities from 75 % up to 91 %, using C12 to C18 fatty acids. Overall, our results demonstrate the potential of a recent CYP and its variants for sustainable and green production of high‐value HFAs.

  摘要细胞色素 P450s（CYPs）对脂肪酸的酶促羟基化为获得羟基脂肪酸（HFAs）提供了一条生态友好的途径，羟基脂肪酸是一种高价值的油脂化学品，在材料工业中具有多种用途，并具有作为生物活性化合物的潜力。然而，CYPs 的不稳定性和区域选择性差是其主要缺点。新发现的一种自给自足的 CYP102 酶，即来自淀粉芽孢杆菌 DSM 7 的 BAMF0695，表现出对脂肪酸亚端位置（ω-1、ω-2 和 ω-3）羟基化的偏好。我们的研究表明，BAMF0695 具有广泛的最适温度（在 20 至 50 °C 之间保持 70% 以上的最大酶活性）和高度的热稳定性（T50 >50 °C），为生物工艺提供了极好的适应性。我们进一步证明，BAMF0695 可以利用可再生微藻脂质作为底物原料生产氢氟烷烃。此外，通过广泛的定点突变和定点饱和突变，我们分离出了具有高区域选择性的变体，这对于通常会产生复杂区域异构体混合物的 CYPs 来说是一种罕见的特性。BAMF0695 突变体能够利用 C12 至 C18 脂肪酸生成单一的氢氟羧酸外消旋体（ω-1 或 ω-2），选择性从 75% 到 91%。总之，我们的研究结果证明了一种最新的 CYP 及其变体在可持续绿色生产高价值氢氟烷烃方面的潜力。