(R)-3-hydroxy-undec-10-enoic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (R)-3-hydroxy-undec-10-enoic acid
• 英文别名: (r)-3-Hydroxy-10-undecenoic acid；(3R)-3-hydroxyundec-10-enoic acid
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: VATLWWDLSNGELA-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-十一烯酸 在 potassium chloride 、 双氧水 、 cytochrome P450_BSβ hydroxylase L78I Q85H G290I variant 作用下， 以 aq. phosphate buffer 、 乙醇 为溶剂， 反应 1.0h， 以75%的产率得到(R)-3-hydroxy-undec-10-enoic acid
  参考文献：
  名称：

  脂肪族羧酸中未活化 C-H 键的生物催化对映选择性 β-羟基化

  摘要：

  定向进化使 P450 BSβ能够β-羟基化脂肪族羧酸中未活化的 C-H 键，具有广泛的底物范围和优异的化学选择性、区域选择性和对映选择性。进化变体的晶体结构使改进的反应性和选择性合理化。这项研究证明了探索生物催化剂以实现化学策略难以实现的反应的潜力。

  DOI：

  10.1002/anie.202204290

文献信息

• ENGINEERED STRAIN OF ESCHERICHIA COLI FOR PRODUCTION OF POLY-R-3-HYDROXYALKANOATE POLYMERS WITH DEFINED MONOMER UNIT COMPOSITION AND METHODS BASED THEREON
  申请人：The Research Foundation for The State University of New York

  公开号：US20160076064A1

  公开（公告）日：2016-03-17

  Methods and systems for producing prescribed unit size azido-poly(3-hydroxyalkanoate) (azido-PHA) polymers and copolymers are provided. The methods and systems can employ recombinant bacteria that are not native producers of PHA or lack enzymes to degrade PHA once synthesized, metabolize short to long chain fatty acids without induction, and express an (R)-specific enoyl-CoA hydratase and a PHA synthase, the (R)-specific enoyl-CoA hydratase and PHA synthase having wide substrate specificities. The recombinant bacteria are fed at least one ω-azidofatty acid substrate that is equal in carbon length to the prescribed or desired unit size of an azido-PHA polymer to be produced. Azido-PHA polymers or azido-PHA co-polymers can be conjugated via copper-catalyzed alkyne-azide cycloaddition (CuAAC) or strain-promoted azide-alkyne cycloaddition (SPAAC) reactions. The prescribed unit size conjugated azido-PHA polymer or orthogonally conjugated azido-PHA co-polymer that is produced is then isolated and/or purified.

  提供了生产规定单元大小的偶氮基聚(3-羟基脂肪酸酯) (azido-PHA)聚合物和共聚物的方法和系统。该方法和系统可以使用重组细菌，这些细菌不是PHA的天然产生者，或者缺乏合成PHA后降解PHA的酶，可以代谢短至长链脂肪酸而无需诱导，并表达(R)-特异性烯酰辅酶A水合酶和PHA合酶，其中(R)-特异性烯酰辅酶A水合酶和PHA合酶具有广泛的底物特异性。重组细菌至少被喂养一种ω-偶氮基脂肪酸底物，该底物的碳长度等于要生产的azido-PHA聚合物的规定或期望单元大小。通过铜催化的炔-偶氮基环加成(CuAAC)或应变促进的偶氮基-炔基环加成(SPAAC)反应，可以将偶氮基-PHA聚合物或偶氮基-PHA共聚物共轭。然后分离和/或纯化所生产的规定单元大小共轭偶氮基-PHA聚合物或正交共轭偶氮基-PHA共聚物。
• Engineered strain of Escherichia coli for production of poly-R-3-hydroxyalkanoate polymers with defined monomer unit composition and methods based thereon
  申请人：The Research Foundation for The State University of New York

  公开号：US10005880B2

  公开（公告）日：2018-06-26

  Methods and systems for producing prescribed unit size azido-poly(3-hydroxyalkanoate) (azido-PHA) polymers and copolymers are provided. The methods and systems can employ recombinant bacteria that are not native producers of PHA or lack enzymes to degrade PHA once synthesized, metabolize short to long chain fatty acids without induction, and express an (R)-specific enoyl-CoA hydratase and a PHA synthase, the (R)-specific enoyl-CoA hydratase and PHA synthase having wide substrate specificities. The recombinant bacteria are fed at least one ω-azidofatty acid substrate that is equal in carbon length to the prescribed or desired unit size of an azido-PHA polymer to be produced. Azido-PHA polymers or azido-PHA co-polymers can be conjugated via copper-catalyzed alkyne-azide cycloaddition (CuAAC) or strain-promoted azide-alkyne cycloaddition (SPAAC) reactions. The prescribed unit size conjugated azido-PHA polymer or orthogonally conjugated azido-PHA co-polymer that is produced is then isolated and/or purified.

  提供了生产规定单位尺寸的叠氮-聚（3-羟基烷酸）（叠氮-PHA）聚合物和共聚物的方法和系统。这些方法和系统可采用重组细菌，这些细菌不是 PHA 的原生生产者，或缺乏一旦合成 PHA 即降解 PHA 的酶，可在无诱导的情况下代谢短链到长链脂肪酸，并表达 (R) 特异性烯酰-CoA 水合酶和 PHA 合成酶，(R) 特异性烯酰-CoA 水合酶和 PHA 合成酶具有广泛的底物特异性。给重组细菌喂食至少一种ω-叠氮脂肪酸底物，该底物的碳长与要生产的叠氮-PHA 聚合物的规定或所需单位大小相等。叠氮-PHA 聚合物或叠氮-PHA 共聚物可通过铜催化的炔吖啶环加成反应（CuAAC）或应变促进的叠氮-炔吖啶环加成反应（SPAAC）进行共轭。然后分离和/或纯化制得的规定单位尺寸共轭叠氮-PHA 聚合物或正交共轭叠氮-PHA 共聚物。
• Tailored Biosynthesis of Olefinic Medium-Chain-Length Poly[(<i>R</i>)-3-hydroxyalkanoates] in <i>Pseudomonas </i><i>p</i><i>utida</i> GPo1 with Improved Thermal Properties
  作者：René Hartmann、Roland Hany、Thomas Geiger、Thomas Egli、Bernard Witholt、Manfred Zinn

  DOI：10.1021/ma040035+

  日期：2004.9.1

  Mixtures of 5-phenylvalerate, octanoate, and 10-undecenoate were fed to a chemostat culture (dilution rate = 0.1 h(-1)) of Pseudomonas putida GPo1 under well-defined dual-(C,N)-nutrient limited growth conditions. Five new, tailor-made copolymers were produced and consisted of poly(3-hydroxy-5-phenylvalerate-co-3-hydroxyalkanoates-co-3-hydroxy-omega-alkenoates), poly(HP-co-HA-co-HE), with increasing amounts of aromatic side chains (A, 0%; B, 3%; C, 19%; D, 42%; and E, 59%), approximately 10 mol % unsaturated side chains, and decreasing amounts of saturated side chains. On the basis of NMR analysis of polymer E, it was concluded that the incorporation of the substrates occurred randomly. The HP-content determined the glass transition temperature, which increased linearly from -38.7 degreesC for poly-(0%HP-co-90%HA-co-10%HE) to -6.0 degreesC for poly(59%HP-omega-31%HA-co-10%HE).
• ENGINEERED STRAIN OF ESCHERICHIA COLI FOR PRODUCTION OF POLY-R-3 HYDROXYALKONOATE POLYMERS WITH DEFINED MONOMER UNIT COMPOSITION AND METHODS BASED THEREON.
  申请人：Suny Research Foundation

  公开号：EP2812438B1

  公开（公告）日：2019-03-13
• Biocatalytic Enantioselective β‐Hydroxylation of Unactivated C−H Bonds in Aliphatic Carboxylic Acids
  作者：Kun Zhang、Aiqin Yu、Xuan Chu、Fudong Li、Juan Liu、Lin Liu、Wen‐Ju Bai、Chao He、Xiqing Wang

  DOI：10.1002/anie.202204290

  日期：2022.7.11

  Directed evolution rendered P450BSβ capable of β-hydroxylating unactivated C−H bonds in aliphatic carboxylic acids with broad substrate scope and excellent chemo-, regio-, and enantioselectivity. The crystal structure of the evolved variant rationalizes the improved reactivity and selectivity. This study demonstrates the potential of exploring biocatalysts to fulfill reactions that are otherwise elusive

  定向进化使 P450 BSβ能够β-羟基化脂肪族羧酸中未活化的 C-H 键，具有广泛的底物范围和优异的化学选择性、区域选择性和对映选择性。进化变体的晶体结构使改进的反应性和选择性合理化。这项研究证明了探索生物催化剂以实现化学策略难以实现的反应的潜力。