5-hydroxy-4-oxohexanoic acid | 7303-37-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 5-hydroxy-4-oxohexanoic acid
• 英文别名: 5-Hydroxy-4-ketohexansaeure；5-Hydroxy-4-oxo-hexansaeure
• CAS: 7303-37-9；44919-75-7
• 化学式: C₆H₁₀O₄
• mdl: MFCD19229066
• 分子量: 146.143
• InChiKey: XXDQOOOVVVJHJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  alpha-酮戊二酸 、 乙醛 在 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase 、 焦磷酸硫胺素 、 magnesium chloride 作用下， 以 aq. phosphate buffer 、 重水 为溶剂， 生成 5-hydroxy-4-oxohexanoic acid
  参考文献：
  名称：

  α-Hydroxy-β-keto acid rearrangement–decarboxylation: impact on thiamine diphosphate-dependent enzymatic transformations

  摘要：

  依赖硫胺二磷酸（ThDP）的MenD催化α-酮戊二酸与丙酮酸的反应，选择性地形成4-羟基-5-氧代己酸2，这似乎与生理底物α-酮戊二酸的酰基供体角色不一致。相比之下，α-酮戊二酸与乙醛的反应仅生成预期的5-羟基-4-氧代区位异构体1。这些反应通过核磁共振（NMR）和圆二色谱（CD）进行了研究，结果表明，与丙酮酸的反应中，观察到的区位选择性是由于最初形成的α-羟基-β-酮酸的重排-脱羧反应，而不是供体-受体底物角色的变化。进一步针对其他依赖ThDP的酶进行的实验，如YerE、SucA和CDH，验证了这种退化性脱羧反应可以与ThDP依赖的酶促转化中常见的酰醇的较低对映选择性相关。

  DOI：

  10.1039/c2ob26981c

文献信息

• METHOD FOR PRODUCING POLYHYDRIC PHENOL
  申请人：Kitagawa Hideo

  公开号：US20120046498A1

  公开（公告）日：2012-02-23

  The present invention is a method for producing a polyhydric phenol, including the following steps (a) to (d): (a) a first step of producing (4S,5R,6S)-4,5,6-trihydroxy-2-cyclohexcene- 1 -one from 2-deoxy-scyllo-inosose by a dehydration reaction; (b) a second step of producing 1,2,4-trihydroxybenzene from the (4S,5R,6S)-4,5,6-trihydroxy-2-cyclohexene- 1 -one obtained in the first step by a dehydration reaction; (c) a third step of producing 4-hydroxycyclohexane-1,3-dione from the 1,2,4-trihydroxybenzene by a catalytic hydrogenation reaction with the use of a metal catalyst; and (d) a fourth step of producing hydroquinone by heating the 4-hydroxycyclohexane-1,3-dione.

  本发明涉及一种生产多羟基苯酚的方法，包括以下步骤（a）至（d）：（a）第一步，通过脱水反应从2-去氧-赤藓糖生成（4S，5R，6S）-4,5,6-三羟基-2-环己烯-1-酮；（b）第二步，通过脱水反应从第一步得到的（4S，5R，6S）-4,5,6-三羟基-2-环己烯-1-酮生成1,2,4-三羟基苯；（c）第三步，使用金属催化剂进行催化氢化反应，从1,2,4-三羟基苯生成4-羟基环己烷-1,3-二酮；（d）第四步，通过加热4-羟基环己烷-1,3-二酮生成对苯二酚。
• MICROORGANISMS FOR THE PRODUCTION OF ADIPIC ACID AND OTHER COMPOUNDS
  申请人：BURGARD Anthony P.

  公开号：US20120309062A1

  公开（公告）日：2012-12-06

  The invention provides a non-naturally occurring microbial organism having an adipate, 6-aminocaproic acid or caprolactam pathway. The microbial organism contains at least one exogenous nucleic acid encoding an enzyme in the respective adipate, 6-aminocaproic acid or caprolactam pathway. The invention additionally provides a method for producing adipate, 6-aminocaproic acid or caprolactam. The method can include culturing an adipate, 6-aminocaproic acid or caprolactam producing microbial organism, where the microbial organism expresses at least one exogenous nucleic acid encoding an adipate, 6-aminocaproic acid or caprolactam pathway enzyme in a sufficient amount to produce the respective product, under conditions and for a sufficient period of time to produce adipate, 6-aminocaproic acid or caprolactam.
• US4902512A
  申请人：——

  公开号：US4902512A

  公开（公告）日：1990-02-20
• α-Hydroxy-β-keto acid rearrangement–decarboxylation: impact on thiamine diphosphate-dependent enzymatic transformations
  作者：Maryam Beigi、Sabrina Loschonsky、Patrizia Lehwald、Volker Brecht、Susana L. A. Andrade、Finian J. Leeper、Werner Hummel、Michael Müller

  DOI：10.1039/c2ob26981c

  日期：——

  The thiamine diphosphate (ThDP) dependent MenD catalyzes the reaction of α-ketoglutarate with pyruvate to selectively form 4-hydroxy-5-oxohexanoic acid 2, which seems to be inconsistent with the assumed acyl donor role of the physiological substrate α-KG. In contrast the reaction of α-ketoglutarate with acetaldehyde gives exclusively the expected 5-hydroxy-4-oxo regioisomer 1. These reactions were studied by NMR and CD spectroscopy, which revealed that with pyruvate the observed regioselectivity is due to the rearrangement–decarboxylation of the initially formed α-hydroxy-β-keto acid rather than a donor–acceptor substrate role variation. Further experiments with other ThDP-dependent enzymes, YerE, SucA, and CDH, verified that this degenerate decarboxylation can be linked to the reduced enantioselectivity of acyloins often observed in ThDP-dependent enzymatic transformations.

  依赖硫胺二磷酸（ThDP）的MenD催化α-酮戊二酸与丙酮酸的反应，选择性地形成4-羟基-5-氧代己酸2，这似乎与生理底物α-酮戊二酸的酰基供体角色不一致。相比之下，α-酮戊二酸与乙醛的反应仅生成预期的5-羟基-4-氧代区位异构体1。这些反应通过核磁共振（NMR）和圆二色谱（CD）进行了研究，结果表明，与丙酮酸的反应中，观察到的区位选择性是由于最初形成的α-羟基-β-酮酸的重排-脱羧反应，而不是供体-受体底物角色的变化。进一步针对其他依赖ThDP的酶进行的实验，如YerE、SucA和CDH，验证了这种退化性脱羧反应可以与ThDP依赖的酶促转化中常见的酰醇的较低对映选择性相关。