3-hydroxy-3-methyl-pent-4-enoic acid | 38004-74-9

• 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: 3-hydroxy-3-methyl-pent-4-enoic acid
• 英文别名: 3-Hydroxy-3-methyl-pent-4-ensaeure；3-Hydroxy-3-methylpent-4-enoic acid
• CAS: 38004-74-9
• 化学式: C₆H₁₀O₃
• mdl: MFCD19228600
• 分子量: 130.144
• InChiKey: JZWQNRBDWROLMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  3-hydroxy-3-methyl-pent-4-enoic acid 在 碘 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 生成 (4R,5R)-4-Hydroxy-5-iodomethyl-4-methyl-dihydro-furan-2-one 、 rel-(4R,5S)-dihydro-4-hydroxy-5-(iodomethyl)-4-methyl-2(3H)-furanone
  参考文献：
  名称：

  含有内部亲核试剂的烯丙醇衍生物的碘环化。通过无环前体中的取代基控制立体选择性

  摘要：

  La 反应 d'acides hydroxy-3 alcene-4oiques avec l'iode en milieu biphasique neutre donne une 环化立体选择性习惯 en cis-hydroxy-3 iodo-4 内酯。替代物的作用

  DOI：

  10.1021/ja00356a020
• 作为产物：
  描述：

  3-hydroxy-3-methyl-pent-4-enoic acid methyl ester 在 氢氧化钾 作用下， 生成 3-hydroxy-3-methyl-pent-4-enoic acid
  参考文献：
  名称：

  Cornforth et al., Biochemical Journal, 1958, vol. 69, p. 146,154

  摘要：

  DOI：

文献信息

• Synthesis of unsaturated hydroxy acids by the cobalt carbonyl and phase transfer catalyzed carbonylation of vinyl epoxides
  作者：Howard Alper、Serge Calet

  DOI：10.1016/s0040-4039(00)82036-5

  日期：1988.1

  Phase transfer catalyzed reaction of vinyl epoxides with carbon monoxide, methyl iodide, catalytic amounts of cobalt carbonyl and TDA-1, affords β-hydroxy acids. High regioselectivity was observed in some cases.

  乙烯基环氧化物与一氧化碳，碘甲烷，催化量的羰基钴和TDA-1的相转移催化反应，得到β-羟基酸。在某些情况下，观察到较高的区域选择性。
• DIPHOSPHOMEVALONATE DECARBOXYLASE VARIANT AND METHOD FOR PRODUCING OLEFIN COMPOUND USING SAME
  申请人：Riken

  公开号：EP3521438A1

  公开（公告）日：2019-08-07

  Mutations involving amino acid substitution were introduced into various sites of diphosphomevalonate decarboxylase (MVD), thus preparing a large number of MVD variants. Then, the variants were each evaluated in terms of a catalytic activity for production of olefin compounds such as isoprene. As a result, it was found that substitution of glycine at position 152 with a different amino acid resulted in improvement in the catalytic activity. In addition, it was found that the MVD in which arginine at position 74 and threonine at position 209 in addition to the position 152 were further substituted with different amino acids, respectively, also had the high catalytic activity.

  在二磷酸戊二酸脱羧酶（MVD）的不同位点引入了涉及氨基酸取代的突变，从而制备了大量的 MVD 变体。然后，对这些变体生产烯烃化合物（如异戊二烯）的催化活性进行了评估。结果发现，用不同的氨基酸取代位置 152 上的甘氨酸可提高催化活性。此外，研究还发现，除位置 152 外，位置 74 的精氨酸和位置 209 的苏氨酸分别被不同的氨基酸进一步取代的 MVD 也具有很高的催化活性。
• Production of alkenes from 3-hydroxycarboxylic acids via 3-hydroxycarboxyl-nucleotidylic acids
  申请人：Global Bioenergies

  公开号：US10017787B2

  公开（公告）日：2018-07-10

  The application describes a method for producing alkenes (for example propylene, ethylene, 1-butylene, isobutylene, isoamylene, butadiene or isoprene) from 3-hydroxycarboxylic acids via 3-hydroxycarboxyl-nucleotidylic acids.

  该申请介绍了一种通过 3-羟基羧基核苷酸从 3-羟基羧基酸生产烯类（例如丙烯、乙烯、1-丁烯、异丁烯、异戊二烯、丁二烯或异戊二烯）的方法。
• Diphosphomevalonate decarboxylase variant, and method for producing olefin compound by using the same
  申请人：RIKEN

  公开号：US10781460B2

  公开（公告）日：2020-09-22

  A method which enables olefin compound production with a high productivity and an enzyme used in the method, a mutation involving amino acid substitution has been introduced into various sites of diphosphomevalonate decarboxylase (MVD), thus preparing a large number of MVD variants. Next, the result of evaluating the variants for the catalytic activity related to the production of olefin compounds such as isoprene has revealed that MVD whose threonine at position 209 is substituted with a different amino acid has the catalytic activity, and that MVD whose arginine at position 74 is further substituted with a different amino acid in addition to position 209 has the catalytic activity at higher levels.

  在二磷酸戊二酸脱羧酶（MVD）的不同位点上引入了涉及氨基酸置换的突变，从而制备出大量 MVD 变体，这种方法能够以较高的生产率生产烯烃化合物，并在该方法中使用酶。接下来，对这些变体进行与生产烯烃化合物（如异戊二烯）有关的催化活性评估的结果表明，209 位苏氨酸被不同氨基酸取代的 MVD 具有催化活性，而 74 位精氨酸除 209 位外还被不同氨基酸取代的 MVD 具有更高水平的催化活性。
• Diphosphomevalonate decarboxylase variant and method for producing olefin compound by using the same
  申请人：RIKEN

  公开号：US10961548B2

  公开（公告）日：2021-03-30

  Mutations involving amino acid substitution were introduced into various sites of diphosphomevalonate decarboxylase (MVD), thus preparing a large number of MVD variants. Then, the variants were each evaluated in terms of a catalytic activity for production of olefin compounds such as isoprene. As a result, it was found that substitution of glycine at position with a different amino acid resulted in improvement in the catalytic activity. In addition, it was found that the MVD in which arginine at position and threonine at position in addition to the position were further substituted with different amino acids, respectively, also had the high catalytic activity.

  在二磷酸戊二酸脱羧酶（MVD）的不同位点引入了涉及氨基酸取代的突变，从而制备了大量的 MVD 变体。然后，对这些变体生产烯烃化合物（如异戊二烯）的催化活性进行了评估。结果发现，用不同的氨基酸取代位置上的甘氨酸可提高催化活性。此外，研究还发现，除了位置上的精氨酸和位置上的苏氨酸外，分别用不同的氨基酸进一步取代的 MVD 也具有很高的催化活性。