(2S,3S)-2-Chloro-3-hydroxy-pentanoic acid ethyl ester | 832110-34-6

• 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: (2S,3S)-2-Chloro-3-hydroxy-pentanoic acid ethyl ester
• 英文别名: Ethyl (2S,3S)-2-chloro-3-hydroxypentanoate；ethyl (2S,3S)-2-chloro-3-hydroxypentanoate
• CAS: 832110-34-6
• 化学式: C₇H₁₃ClO₃
• 分子量: 180.631
• InChiKey: FMQZXQLKFZJTPZ-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氯-3-氧代戊酸乙酯 在 KP_i 、 YGL₁₅₇w GST-fusion protein from Saccharomyces cerevisiae D-葡萄糖-6-磷酸 、 烟酰胺腺嘌呤双核苷酸磷酸盐 、 glucose 6-phosphate dehydrogenase 作用下， 生成 (2S,3S)-2-Chloro-3-hydroxy-pentanoic acid ethyl ester
  参考文献：
  名称：

  Stereoselective, Biocatalytic Reductions of α-Chloro-β-keto Esters

  摘要：

  Eighteen known and putative reductases from baker's yeast (Saccharomyces cerevisiae) were tested for the ability to reduce a series of alpha-chloro-beta-keto esters. In nearly all cases, it was possible to produce at least two of the four possible alpha-chloro-beta-hydroxy ester diastereomers with high optical purities. The utility of this approach was demonstrated by reducing ethyl 2-chloroacetoacetate to the corresponding Syn-(2R,3S)-alcohol on a multigram scale using whole cells of an Escherichia coli strain overexpressing a single yeast reductase identified from the screening studies.

  DOI：

  10.1021/jo0484981

文献信息

• Stereoselective, Biocatalytic Reductions of α-Chloro-β-keto Esters
  作者：Iwona A. Kaluzna、Brent D. Feske、Weerawut Wittayanan、Ion Ghiviriga、Jon D. Stewart

  DOI：10.1021/jo0484981

  日期：2005.1.1

  Eighteen known and putative reductases from baker's yeast (Saccharomyces cerevisiae) were tested for the ability to reduce a series of alpha-chloro-beta-keto esters. In nearly all cases, it was possible to produce at least two of the four possible alpha-chloro-beta-hydroxy ester diastereomers with high optical purities. The utility of this approach was demonstrated by reducing ethyl 2-chloroacetoacetate to the corresponding Syn-(2R,3S)-alcohol on a multigram scale using whole cells of an Escherichia coli strain overexpressing a single yeast reductase identified from the screening studies.