(S)-(+)-2-hydroxy-3-mercaptopropionic acid | 30163-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-(+)-2-hydroxy-3-mercaptopropionic acid
• 英文别名: L(-)-2-Hydroxy-3-mercapto-propansaeure；(R)-2-hydroxy-3-mercaptopropanoic acid；(2R)-2-hydroxy-3-sulfanylpropanoic acid
• CAS: 30163-02-1
• 化学式: C₃H₆O₃S
• 分子量: 122.145
• InChiKey: OLQOVQTWRIJPRE-REOHCLBHSA-N

物化性质

• 沸点：
  325.8±32.0 °C(Predicted)
• 密度：
  1.443±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  58.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 (S)-(+)-2-hydroxy-3-mercaptopropionic acid 在 硫酸 作用下， 反应 15.0h， 以80%的产率得到(R)-(-)-methyl 2-hydroxy-3-mercaptopropionate
  参考文献：
  名称：

  Molecular requirements of the recognition site of cholinergic receptors. 22. Resolution, absolute configuration, and cholinergic enantioselectivity of (+)- and (-)-cis-2-methyl-5-[(dimethylamino)methyl]-1,3-oxathiolane methiodide

  摘要：

  The potent cholinergic agonist (+/-)-cis-2-methyl-5-[(dimethylamino)methyl]-1,3-oxathiolane methiodide (+/-)-1] was resolved into enantiomeric forms. Their absolute configurations were established by a synthetic pathway that also allowed the synthesis of the corresponding diastereomeric (+)- and (-)-trans-2-methyl-5-[(dimethylamino)-methyl]-1,3-oxathiolane methiodide [(+)- and (-)-10]. Compound (+)-1, which is the most potent of the four isomers, showed the same absolute configuration as L-(+)-muscarine and (+)-cis-dioxolane. The four isomers were tested on guinea pig ileum and frog rectus abdominis, and their muscarinic and nicotinic potency (EPMR) and selectivity were determined. The relationships between stereoisomerism and potency are discussed.

  DOI：

  10.1021/jm00159a009
• 作为产物：
  描述：

  (S)-(+)-2-hydroxy-3-benzylthiopropanoic acid 在 氨 、 sodium 作用下， 生成 (S)-(+)-2-hydroxy-3-mercaptopropionic acid
  参考文献：
  名称：

  S-苄基半胱氨酸和半胱氨酸的α-羟基类似物的合成

  摘要：

  将β-氯乳酸与甲苯-α-硫醇缩合，得到2-羟基-3-苄基硫代丙酸。旋光异构体是通过苯丙氨酸和奎宁拆分而制备的。除去苄基得到（+）-和（-）-2-羟基-3-巯基丙酸。用阮内镍脱硫得到（+）-和（-）-乳酸。已经确定了所有异构体的构型和光学纯度。

  DOI：

  10.1039/j39700002475

文献信息

• Sporothioethers: deactivated alkyl citrates from the fungus <i>Hypomontagnella monticulosa</i>
  作者：Henrike Heinemann、Kevin Becker、Hedda Schrey、Haoxuan Zeng、Marc Stadler、Russell J. Cox

  DOI：10.1039/d3ra06542a

  日期：——

  Two new thioether specialised metabolites isolated from the fungus Hypomontagnella monticulosa show attenuated antifungal properties, but retain biofilm inhibition activity.

  从单端孢霉（Hypomontagnella monticulosa）中分离出的两种新的硫醚特化代谢物显示出减弱的抗真菌特性，但仍具有抑制生物膜的活性。
• Waelti,M.; Hope,D.B., Journal of the Chemical Society C: Organic, 1971, p. 2326 - 2328
  作者：Waelti,M.、Hope,D.B.

  DOI：——

  日期：——
• TEODORI E.; GUALTIERI F.; ANGELI P.; BRASILI L.; GIANNELLA M.; PIGINI M., J. MED. CHEM., 29,(1986) N 9, 1610-1615
  作者：TEODORI E.、 GUALTIERI F.、 ANGELI P.、 BRASILI L.、 GIANNELLA M.、 PIGINI M.

  DOI：——

  日期：——
• Synthesis of the α-hydroxy-analogues of S-benzylcysteine and cysteine
  作者：D. B. Hope、M. Wälti

  DOI：10.1039/j39700002475

  日期：——

  β-Chlorolactic acid was condensed with toluene-α-thiol to give 2-hydroxy-3-benzylthiopropanoic acid. The optical isomers were prepared by resolution with brucine and quinine. Removal of benzyl groups yielded (+)- and (–)-2-hydroxy-3-mercaptopropanoic acid. Desulphurization with Raney nickel gave (+)- and (–)-lactic acid. Configuration and optical purity of all isomers have been determined.

  将β-氯乳酸与甲苯-α-硫醇缩合，得到2-羟基-3-苄基硫代丙酸。旋光异构体是通过苯丙氨酸和奎宁拆分而制备的。除去苄基得到（+）-和（-）-2-羟基-3-巯基丙酸。用阮内镍脱硫得到（+）-和（-）-乳酸。已经确定了所有异构体的构型和光学纯度。
• Molecular requirements of the recognition site of cholinergic receptors. 22. Resolution, absolute configuration, and cholinergic enantioselectivity of (+)- and (-)-cis-2-methyl-5-[(dimethylamino)methyl]-1,3-oxathiolane methiodide
  作者：Elisabetta Teodori、Fulvio Gualtieri、Piero Angeli、Livio Brasili、Mario Giannella、Maria Pigini

  DOI：10.1021/jm00159a009

  日期：1986.9

  The potent cholinergic agonist (+/-)-cis-2-methyl-5-[(dimethylamino)methyl]-1,3-oxathiolane methiodide (+/-)-1] was resolved into enantiomeric forms. Their absolute configurations were established by a synthetic pathway that also allowed the synthesis of the corresponding diastereomeric (+)- and (-)-trans-2-methyl-5-[(dimethylamino)-methyl]-1,3-oxathiolane methiodide [(+)- and (-)-10]. Compound (+)-1, which is the most potent of the four isomers, showed the same absolute configuration as L-(+)-muscarine and (+)-cis-dioxolane. The four isomers were tested on guinea pig ileum and frog rectus abdominis, and their muscarinic and nicotinic potency (EPMR) and selectivity were determined. The relationships between stereoisomerism and potency are discussed.