(3R,7Z)-3-hydroxy-7-tetradecenoic acid | 1025737-52-3

• 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: (3R,7Z)-3-hydroxy-7-tetradecenoic acid
• 英文别名: (R,Z)-3-hydroxytetradec-7-enoic acid；(Z,3R)-3-hydroxytetradec-7-enoic acid
• CAS: 1025737-52-3
• 化学式: C₁₄H₂₆O₃
• 分子量: 242.359
• InChiKey: XEDLAVDOPNIEBY-MEJMFZKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 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：

  (3R,7Z)-3-hydroxy-7-tetradecenoic acid 、 (R)-(+)-alpha-氨基-gamma-丁内酯盐酸盐 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以77%的产率得到(2R,3'R,7'Z)-N-(3'-hydroxy-7'-tetradecenoyl)-L-homoserine lactone
  参考文献：
  名称：

  Synthesis and Stereochemistry-Activity Relationship of small Bacteriocin, an Autoinducer of the Symbiotic Nitrogen-Fixing Bacterium Rhizobium leguminosarum

  摘要：

  The four stereoisomers of small bacteriocin, an autoinducer of the symbiotic nitrogen-fixing bacterium Rhizobium leguminosarum, were synthesized via a versatile methodology for 3'-hydroxyacyl homoserine lactones based on the Nagao asymmetric aldol reaction. The synthetic isomers were much less effective at inhibiting the growth of R. leguminosarum RBL5523 than the natural isomer, showing the importance of stereochemistry for activity.

  DOI：

  10.1021/ol8005198
• 作为产物：
  描述：

  (3R,7Z)-ethyl 3-hydroxy-7-tetradecanoate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以87%的产率得到(3R,7Z)-3-hydroxy-7-tetradecenoic acid
  参考文献：
  名称：

  （2对映选择性合成小号，3' - [R，7' ž - ）ñ - （3'-羟基-7'- tetradecenoyl）高丝氨酸内酯

  摘要：

  （2的简明对映选择性全合成小号，3' - [R，7' ž - ）ñ - （3'-羟基-7'- tetradecenoyl）高丝氨酸内酯进行说明。该方案的主要特点是催化不对称氢化和亚胺反应中前苯酚-锌催化的重氮加成反应是手性的成因。而且，在合成中建立了灵活性，以使用催化量的对映体富集的C 2对称配体来产生对映体富集的类似物。

  DOI：

  10.1016/j.tetlet.2010.09.138

文献信息

• A METHOD FOR PRODUCING HYDROXYCARBOXYLIC ACIDS BY AUTO-DEGRADATION OF POLYHYDROXYALKANOATES
  申请人：ChiroBio Inc.

  公开号：EP1036190B1

  公开（公告）日：2005-05-11
• US6472188B1
  申请人：——

  公开号：US6472188B1

  公开（公告）日：2002-10-29
• [EN] METHOD FOR THE PRODUCTION OF R-HYDROXYCARBOXYLIC ACIDS<br/>[FR] PROCÉDÉ DE FABRICATION D'ACIDES R-HYDROXYCARBOXYLIQUES
  申请人：EMPA

  公开号：WO2008113190A1

  公开（公告）日：2008-09-25

  [EN] The present invention provides a method for production of enantiomerically pure R-hydroxycarboxylic acids by in vivo degradation of biopolymer polyhydroxyalkanoates (PHAs). The method comprises the steps of: 1) synthesizing PHAs by cultivating microorganisms in batch, fed-batch, or continuous cultures; 2) adjusting the pH of the culture to a level allowing the enzymatic depolymerization of said PHAs into one or more corresponding monomeric RHAs and the secretion of said RHAs into the culture medium; 3) incubating the culture at a set pH; 4) acidifying the pH of said culture and 5) optionally purifying the RHA monomers. The present process gives high product purity and yield, leads to effective cost reduction, easy downstream processing and environmentally friendly. Furthermore, the invention encompasses a plant for the production of R-hydroxycarboxylic acids (RHAs) by in vivo depolymerization of PHAs.
  [FR] La présente invention porte sur un procédé de production d'acides R-hydroxycarboxyliques énantiomériquement purs par dégradation in vivo de polyhydroxyalcanoates biopolymères (PHA). Le procédé comprend les étapes consistant à : 1) synthétiser des PHA par culture de micro-organismes dans des cultures par lots, semi-discontinues ou continues; 2) ajuster le pH de la culture à un niveau permettant la dépolymérisation enzymatique desdits PHA en un ou plusieurs RHA monomères correspondants et la sécrétion desdits RHA dans le milieu de culture; 3) faire incuber la culture à un pH défini; 4) acidifier le pH de ladite culture et 5) facultativement purifier les monomères RHA. Le présent procédé permet d'obtenir un produit de haute pureté et à haut rendement, une réduction des coûts effective, un traitement en aval aisé et est respectueux de l'environnement. De plus, l'invention porte sur une installation pour la production d'acides R-hydroxycarboxyliques (RHA) par dépolymérisation in vivo des PHA.
• Enantioselective synthesis of (2S,3′R,7′Z)-N-(3′-hydroxy-7′-tetradecenoyl)-homoserine lactone
  作者：Gullapalli Kumaraswamy、Neerasa Jayaprakash

  DOI：10.1016/j.tetlet.2010.09.138

  日期：2010.12

  A concise enantioselective total synthesis of (2S,3′R,7′Z)-N-(3′-hydroxy-7′-tetradecenoyl)-homoserine lactone is described. Key feature of this protocol is a catalytic asymmetric hydrogenation and a prophenol–zinc-catalyzed diazo addition to imine reaction as genesis of chirality. Moreover, flexibility is built in the synthesis to generate enantioenriched analogs using catalytic amount of enantioenriched

  （2的简明对映选择性全合成小号，3' - [R，7' ž - ）ñ - （3'-羟基-7'- tetradecenoyl）高丝氨酸内酯进行说明。该方案的主要特点是催化不对称氢化和亚胺反应中前苯酚-锌催化的重氮加成反应是手性的成因。而且，在合成中建立了灵活性，以使用催化量的对映体富集的C 2对称配体来产生对映体富集的类似物。
• Synthesis and Stereochemistry-Activity Relationship of <i>small</i> Bacteriocin, an Autoinducer of the Symbiotic Nitrogen-Fixing Bacterium <i>Rhizobium leguminosarum</i>
  作者：Arata Yajima、Anton A. N. van Brussel、Jan Schripsema、Tomoo Nukada、Goro Yabuta

  DOI：10.1021/ol8005198

  日期：2008.5.1

  The four stereoisomers of small bacteriocin, an autoinducer of the symbiotic nitrogen-fixing bacterium Rhizobium leguminosarum, were synthesized via a versatile methodology for 3'-hydroxyacyl homoserine lactones based on the Nagao asymmetric aldol reaction. The synthetic isomers were much less effective at inhibiting the growth of R. leguminosarum RBL5523 than the natural isomer, showing the importance of stereochemistry for activity.