(4S)-3-(benzyloxycarbonyl)-4-[(3R)-3-hydroxy-3-deuteriopropyl]-1,3-oxazolidin-5-one | 489469-33-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4S)-3-(benzyloxycarbonyl)-4-[(3R)-3-hydroxy-3-deuteriopropyl]-1,3-oxazolidin-5-one
• 英文别名: benzyl (4S)-4-[(3R)-3-deuterio-3-hydroxypropyl]-5-oxo-1,3-oxazolidine-3-carboxylate
• CAS: 489469-33-2
• 化学式: C₁₄H₁₇NO₅
• 分子量: 280.285
• InChiKey: LFILUXSYTPLDAP-JRWVWRSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S)-3-(benzyloxycarbonyl)-4-[(3R)-3-hydroxy-3-deuteriopropyl]-1,3-oxazolidin-5-one 在 聚甘氨酸 盐酸 、 NosE gene from Escherichia coli 、 β-烟酰胺腺嘌呤二核苷酸 、 zinc(II) sulfate 作用下， 以 水 为溶剂， 反应 7.25h， 生成 (2S,4S)-<4-2H1>-proline
  参考文献：
  名称：

  Biosynthesis of 4-Methylproline in Cyanobacteria:  Cloning of nosE and nosF Genes and Biochemical Characterization of the Encoded Dehydrogenase and Reductase Activities

  摘要：

  The biosynthesis of the unusual amino acid 4-methylproline in the Nostoc genus of cyanobacteria was investigated on the genetic and enzymatic level. Two genes involved in the biosynthesis were cloned and the corresponding enzymes, a zinc-dependent long-chain dehydrogenase and a Delta(1)-pyrroline-5-carboxylic acid (P5C) reductase homologue, were overexpressed in Escherichia coli and biochemically characterized. Putative substrates were synthesized to test enzyme substrate specificities, and deuterium labeling studies were carried out to reveal the stereospecificities of the enzymatic reactions with respect to the substrates as well as to the coenzymes.

  DOI：

  10.1021/jo026479q
• 作为产物：
  描述：

  (4S)-3-(benzyloxycarbonyl)-4-(3-deuterioformylethyl)-1,3-oxazolidin-5-one 在 (S)-alpine borane 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以19%的产率得到(4S)-3-(benzyloxycarbonyl)-4-[(3R)-3-hydroxy-3-deuteriopropyl]-1,3-oxazolidin-5-one
  参考文献：
  名称：

  Biosynthesis of 4-Methylproline in Cyanobacteria:  Cloning of nosE and nosF Genes and Biochemical Characterization of the Encoded Dehydrogenase and Reductase Activities

  摘要：

  The biosynthesis of the unusual amino acid 4-methylproline in the Nostoc genus of cyanobacteria was investigated on the genetic and enzymatic level. Two genes involved in the biosynthesis were cloned and the corresponding enzymes, a zinc-dependent long-chain dehydrogenase and a Delta(1)-pyrroline-5-carboxylic acid (P5C) reductase homologue, were overexpressed in Escherichia coli and biochemically characterized. Putative substrates were synthesized to test enzyme substrate specificities, and deuterium labeling studies were carried out to reveal the stereospecificities of the enzymatic reactions with respect to the substrates as well as to the coenzymes.

  DOI：

  10.1021/jo026479q

文献信息

• Biosynthesis of 4-Methylproline in Cyanobacteria:  Cloning of <i>n</i><i>osE</i> and <i>n</i><i>osF</i> Genes and Biochemical Characterization of the Encoded Dehydrogenase and Reductase Activities
  作者：Hendrik Luesch、Dietmar Hoffmann、Joan M. Hevel、Julia E. Becker、Trimurtulu Golakoti、Richard E. Moore

  DOI：10.1021/jo026479q

  日期：2003.1.1

  The biosynthesis of the unusual amino acid 4-methylproline in the Nostoc genus of cyanobacteria was investigated on the genetic and enzymatic level. Two genes involved in the biosynthesis were cloned and the corresponding enzymes, a zinc-dependent long-chain dehydrogenase and a Delta(1)-pyrroline-5-carboxylic acid (P5C) reductase homologue, were overexpressed in Escherichia coli and biochemically characterized. Putative substrates were synthesized to test enzyme substrate specificities, and deuterium labeling studies were carried out to reveal the stereospecificities of the enzymatic reactions with respect to the substrates as well as to the coenzymes.