(S)-Vinylglycolate | 96243-34-4

• 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: (S)-Vinylglycolate
• 英文别名: (S)-2-Hydroxybut-3-enoic acid；(2S)-2-hydroxybut-3-enoic acid
• CAS: 96243-34-4
• 化学式: C₄H₆O₃
• 分子量: 102.09
• InChiKey: VBWPSWWDYVWZKA-VKHMYHEASA-N

物化性质

• 沸点：
  263.1±20.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  丁烯二醇 在 α-ketoglutarate monoammonium salt 、 β-烟酰胺腺嘌呤二核苷酸 、 1,4-二巯基-2,3-丁二醇 作用下， 生成 (S)-Vinylglycolate
  参考文献：
  名称：

  Enantioselective oxidation of 1,2-diols to L-.alpha.-hydroxy acids using co-immobilized alcohol and aldehyde dehydrogenases as catalysts

  摘要：

  DOI：

  10.1021/jo00211a046

文献信息

• Racemization of Vinylglycolate Catalyzed by Mandelate Racemase
  作者：Rongshi Li、Vincent M. Powers、John W. Kozarich、George L. Kenyon

  DOI：10.1021/jo00116a017

  日期：1995.6

  Vinylglycolate (2-hydroxy-3-butenoic acid, 2) has been found to be an excellent substrate of mandelate racemase. The measured steady-state kinetic parameters for the enantiomers of 2 are comparable, with a maximal racemization rate that is 35% relative to mandelate. Racemization of 2 is subject to a primary deuterium kinetic isotope of about 4, indicating that abstraction of the alpha-proton is at least partially rate-limiting. Although alpha-hydroxybutyrate (5), the saturated analogue of 2, is not a substrate, 5 competitively inhibits racemization of 2 with a K-i value comparable to the average K-m value for the latter. These results implicate the importance of beta,gamma-unsaturation in promoting facile racemization of the substrate alpha-proton. In addition, the enzyme catalyzes the isomerization of 2 to alpha-ketobutyrate (4), with a partition ratio for racemization/isomerization; of about 1 x 10(4). These observations highlight the precision with which mandelate racemase can promote racemization to the virtual exclusion of a thermodynamically more favored process.
• Enantioselective oxidation of 1,2-diols to L-.alpha.-hydroxy acids using co-immobilized alcohol and aldehyde dehydrogenases as catalysts
  作者：Chi Huey Wong、Jose R. Matos

  DOI：10.1021/jo00211a046

  日期：1985.5