2-羟基十四烷二酸 | 80007-21-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2-羟基十四烷二酸
• 英文名称: α-hydroxytetradecanedioic acid
• 英文别名: h Ydroxytetradecanedioic acid；2-hydroxytetradecanedioic acid
• CAS: 80007-21-2
• 化学式: C₁₄H₂₆O₅
• 分子量: 274.357
• InChiKey: HWCBZTXSSOIPNB-UHFFFAOYSA-N

物化性质

• 沸点：
  475.7±15.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (-)-duryne F 在 臭氧 、 甲酸 、 双氧水 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 十一烷二酸 、 2-羟基十四烷二酸
  参考文献：
  名称：

  (−)-Duryne and Its Homologues, Cytotoxic Acetylenes from a Marine Sponge Petrosia sp.

  摘要：

  Six linear acetylenes, (-)-duryne (1) and (-)-durynes B-F (2-6), were isolated from the marine sponge Petrosia sp. Their structures were elucidated by NMR and tandem FABMS analyses. The positions of the olefinic bonds were confirmed by ozonolysis experiments, and the absolute configurations were determined by the modified Mosher's method. Compound 1 was found to be the enantiomer of duryne, a previously reported sponge metabolite. Compounds 1-6 show cytotoxicity against HeLa cells with IC(50) values between 0.08 and 0.50 mu M.

  DOI：

  10.1021/np200271n

文献信息

• Fatty Acid Chain Shortening by a Fungal Peroxygenase
  作者：Andrés Olmedo、José C. del Río、Jan Kiebist、René Ullrich、Martin Hofrichter、Katrin Scheibner、Angel T. Martínez、Ana Gutiérrez

  DOI：10.1002/chem.201704773

  日期：2017.12.1

  A recently discovered peroxygenase from the fungus Marasmius rotula (MroUPO) is able to catalyze the progressive one-carbon shortening of medium and long-chain mono- and dicarboxylic acids by itself alone, in the presence of H2 O2 . The mechanism, analyzed using H218 O2 , starts with an α-oxidation catalyzed by MroUPO generating an α-hydroxy acid, which is further oxidized by the enzyme to a reactive

  最近发现的一种来自真菌 Marasmius rotula (MroUPO) 的过氧化酶能够在 H2 O2 存在的情况下单独催化中链和长链一元和二元羧酸的逐步单碳缩短。使用 H218 O2 分析该机制，首先由 MroUPO 催化的 α-氧化生成 α-羟基酸，该酸进一步被酶氧化为反应性 α-酮中间体，其脱羧产生一碳较短的脂肪酸。与之前表征的杨树菇过氧化酶相比，更宽的血红素进入通道，使脂肪酸能够将羧基末端定位在血红素辅因子附近（如可用的晶体结构之一所示），这可能是 MroUPO 独特能力的根源缩短羧酸链。
• Enzymatic Oxidative Tandem Decarboxylation of Dioic Acids to Terminal Dienes
  作者：Alexander Dennig、Sara Kurakin、Miriam Kuhn、Andela Dordic、Mélanie Hall、Kurt Faber

  DOI：10.1002/ejoc.201600358

  日期：2016.7

  The biocatalytic oxidative tandem decarboxylation of C7–C18 dicarboxylic acids to terminal C5–C16 dienes was catalyzed by the P450 monooxygenase OleT with conversions up to 29 % for 1,11-dodecadiene (0.49 g L–1). The sequential nature of the cascade was proven by the fact that decarboxylation of intermediate C6–C11 ω-alkenoic acids and heptanedioic acid exclusively gave nonconjugated 1,4-pentadiene;

  C7-C18 二元羧酸到末端 C5-C16 二烯的生物催化氧化串联脱羧由 P450 单加氧酶 OleT 催化，1,11-十二二烯（0.49 g L-1）的转化率高达 29%。中间体 C6-C11 ω-链烯酸和庚二酸的脱羧反应仅生成非共轭 1,4-戊二烯，证明了级联的顺序性质；放大允许分离 1,15-十六二烯和 1,11-十二二烯；该系统代表了一条从可再生二元羧酸获得末端二烯的绿色短途路线。
• PROCESS FOR SHORTENING THE HYDROCARBON CHAIN OF A CARBOXYLIC ACID BY A PEROXYGENASE
  申请人：Consejo Superior de Investigaciones Científicas (CSIC)

  公开号：EP3392341A1

  公开（公告）日：2018-10-24

  The present invention discloses a novel process for the chain shortening of carboxylic acids having a hydrocarbon chain, catalyzed by a peroxygenase, preferably by a fungal peroxygenase from Marasmius rotula (MroUPO), in the presence of a peroxide. The mechanism starts with an α-oxidation generating an α-hydroxy acid, which is further oxidized to a reactive α-keto intermediate whose decarboxylation yields the one-carbon shorter acid.

  本发明公开了一种新型的烃链羧酸短链工艺，该工艺在过氧化物存在的情况下，由一种过氧酶催化，最好是由一种来自 Marasmius rotula（MroUPO）的真菌过氧酶催化。其机理首先是α-氧化产生α-羟基酸，α-羟基酸进一步氧化为活性α-酮中间体，中间体脱羧后产生单碳短酸。
• (−)<i>-</i>Duryne and Its Homologues, Cytotoxic Acetylenes from a Marine Sponge <i>Petrosia</i> sp.
  作者：Yuki Hitora、Kentaro Takada、Shigeru Okada、Yuji Ise、Shigeki Matsunaga

  DOI：10.1021/np200271n

  日期：2011.5.27

  Six linear acetylenes, (-)-duryne (1) and (-)-durynes B-F (2-6), were isolated from the marine sponge Petrosia sp. Their structures were elucidated by NMR and tandem FABMS analyses. The positions of the olefinic bonds were confirmed by ozonolysis experiments, and the absolute configurations were determined by the modified Mosher's method. Compound 1 was found to be the enantiomer of duryne, a previously reported sponge metabolite. Compounds 1-6 show cytotoxicity against HeLa cells with IC(50) values between 0.08 and 0.50 mu M.