(3R)-2-amino-3-[(3-hydroxy-1-propylpropyl)sulfanyl]propanoic acid | 1019195-98-2

• 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: (3R)-2-amino-3-[(3-hydroxy-1-propylpropyl)sulfanyl]propanoic acid
• 英文别名: (2R)-2-amino-3-[(3R)-1-hydroxyhexan-3-yl]sulfanylpropanoic acid
• CAS: 1019195-98-2
• 化学式: C₉H₁₉NO₃S
• 分子量: 221.321
• InChiKey: GTJBXOQYHBJVCS-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R)-2-amino-3-[(3-hydroxy-1-propylpropyl)sulfanyl]propanoic acid 在 乙二胺四乙酸 、 sodium chloride 作用下， 以 水 为溶剂， 以82%的产率得到(-)-(R)-3-mercaptohexan-1-ol
  参考文献：
  名称：

  Synthesis of the Individual Diastereomers of the Cysteine Conjugate of 3-Mercaptohexanol (3-MH)

  摘要：

  The individual diastereoisomers of the cysteine conjugate of 3-mercaptohexanol (4) were synthesized with high isomeric purity (>98%). On treatment with Apotryptophanase enzyme, the 3R diastereoisomer of 4 gave an 82% yield of the R enantiomer of 1, with no trace of the 3S enantiomer present. Conversely, the 3S diastereoisomer of 4 gave the 3S enantiomer of 1 (43%) accompanied by a trace of the 3R form (SIR = 98.5:1.5), reflecting the diastereomeric purity of the cysteine conjugate. The same stereochemical outcome was observed when the individual diastereoisomers of 4 were added to fermentations with the Saccharomyces cerevisiae AWRI 1655 yeast strain, which gave 1 in 1% yield. A d(10)-analogue of 1 was synthesized and used as an internal standard to determine, by gas chromatography-mass spectrometry (GC-MS), the amounts of 1 formed in these transformations.

  DOI：

  10.1021/jf8000444
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (3R)-2-amino-3-[(3-hydroxy-1-propylpropyl)sulfanyl]propanoic acid
  参考文献：
  名称：

  Synthesis of the Individual Diastereomers of the Cysteine Conjugate of 3-Mercaptohexanol (3-MH)

  摘要：

  The individual diastereoisomers of the cysteine conjugate of 3-mercaptohexanol (4) were synthesized with high isomeric purity (>98%). On treatment with Apotryptophanase enzyme, the 3R diastereoisomer of 4 gave an 82% yield of the R enantiomer of 1, with no trace of the 3S enantiomer present. Conversely, the 3S diastereoisomer of 4 gave the 3S enantiomer of 1 (43%) accompanied by a trace of the 3R form (SIR = 98.5:1.5), reflecting the diastereomeric purity of the cysteine conjugate. The same stereochemical outcome was observed when the individual diastereoisomers of 4 were added to fermentations with the Saccharomyces cerevisiae AWRI 1655 yeast strain, which gave 1 in 1% yield. A d(10)-analogue of 1 was synthesized and used as an internal standard to determine, by gas chromatography-mass spectrometry (GC-MS), the amounts of 1 formed in these transformations.

  DOI：

  10.1021/jf8000444

文献信息

• Synthesis of the Individual Diastereomers of the Cysteine Conjugate of 3-Mercaptohexanol (3-MH)
  作者：Kevin H. Pardon、Sean D. Graney、Dimitra L. Capone、Jan H. Swiegers、Mark A. Sefton、Gordon M. Elsey

  DOI：10.1021/jf8000444

  日期：2008.5.1

  The individual diastereoisomers of the cysteine conjugate of 3-mercaptohexanol (4) were synthesized with high isomeric purity (>98%). On treatment with Apotryptophanase enzyme, the 3R diastereoisomer of 4 gave an 82% yield of the R enantiomer of 1, with no trace of the 3S enantiomer present. Conversely, the 3S diastereoisomer of 4 gave the 3S enantiomer of 1 (43%) accompanied by a trace of the 3R form (SIR = 98.5:1.5), reflecting the diastereomeric purity of the cysteine conjugate. The same stereochemical outcome was observed when the individual diastereoisomers of 4 were added to fermentations with the Saccharomyces cerevisiae AWRI 1655 yeast strain, which gave 1 in 1% yield. A d(10)-analogue of 1 was synthesized and used as an internal standard to determine, by gas chromatography-mass spectrometry (GC-MS), the amounts of 1 formed in these transformations.