(2S)-2-羟基-3-巯基丙酸 | 30163-03-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (2S)-2-羟基-3-巯基丙酸
• 英文名称: (S)-2-hydroxy-3-mercaptopropanoic acid
• 英文别名: (2S)-2-hydroxy-3-sulfanylpropanoic acid
• CAS: 30163-03-2
• 化学式: C₃H₆O₃S
• 分子量: 122.145
• InChiKey: OLQOVQTWRIJPRE-UWTATZPHSA-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：

  (2S)-2-羟基-3-巯基丙酸 、 L-Cystin-S-monoxide 以 水 为溶剂， 生成 3,3'-Dithio-L-2-amino-D-2'-hydroxydipropanoic acid
  参考文献：
  名称：

  Waelti,M.; Hope,D.B., Journal of the Chemical Society C: Organic, 1971, p. 2326 - 2328

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-(-)-2-hydroxy-3-benzylthiopropanoic acid 在 氨 、 sodium 作用下， 生成 (2S)-2-羟基-3-巯基丙酸
  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

• Total Synthesis of Berkeleylactone A
  作者：Branislav Ferko、Marián Zeman、Michele Formica、Sebastián Veselý、Jana Doháňošová、Ján Moncol、Petra Olejníková、Dušan Berkeš、Pavol Jakubec、Darren J. Dixon、Ol’ga Caletková

  DOI：10.1021/acs.joc.9b00850

  日期：2019.6.7

  The first total synthesis of the potent antibiotic berkeleylactone A is described in 10 steps with an overall yield of 9.5%. A key step of our concise route is a late-stage, highly diastereoselective, sulfa-Michael addition. The 16-membered macrocyclic lactone was formed via ring closing metathesis and subsequent chemoselective reduction. The absolute stereochemical configuration was confirmed by single-crystal

  以十个步骤描述了有效的抗生素伯克利内酯A的第一个全合成，总收率为9.5％。我们简洁路线的关键步骤是后期非对映选择性高的磺胺-迈克尔加成反应。通过闭环复分解和随后的化学选择性还原形成16元大环内酯。绝对立体化学构型通过单晶X射线分析确认。对几种耐甲氧西林的金黄色葡萄球菌菌株进行了合成伯克内酯A的测试，并验证了其有效的抗菌活性。
• Synthesis and structure–activity relationship of berkeleylactone A-derived antibiotics
  作者：Tomáš Malatinský、Dominika Valachová、Lucia Pinčeková、David Scherhaufer、Petra Olejníková、Magdaléna Májeková、Jarmila Vargová、Barbora Gaálová-Radochová、Helena Bujdáková、Jana Nováčiková、Alistair J. M. Farley、Dušan Berkeš、Pavol Jakubec、Andrej Kolarovič、Oľga Caletková

  DOI：10.1039/d2ob01452a

  日期：——

  Berkeleylactone A is a potent 16-membered macrolactone antibiotic, recently isolated from a coculture of Berkeley Pit Lake fungi. Although its antimicrobial activity has already been investigated, little is known about the structure–activity relationship. Based on our previous synthetic studies, a series of berkeleylactone A derivatives were synthesized and evaluated for their in vitro antimicrobial

  Berkeleylactone A 是一种有效的 16 元大环内酯抗生素，最近从 Berkeley Pit Lake 真菌的共培养物中分离出来。尽管已经对其抗菌活性进行了研究，但对其构效关系知之甚少。基于我们之前的合成研究，合成了一系列伯克利内酯 A 衍生物，并评估了它们对甲氧西林敏感和耐甲氧西林金黄色葡萄球菌(MRSA) 菌株的体外抗菌活性。我们的数据证实了嵌入共轭系统的重要作用，并表明迈克尔受体的可逆磺胺保护是一种可行的选择。结构简化的非手性大环内酰胺8显示出最佳的抑制活性S. aureus L12 (MRSA) 的 MIC 50值为 0.39 μg mL -1，比伯克利内酯 A 低 8 倍。这些研究可能对开发更先进的抗生素应用候选物具有价值。
• 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。
• 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.
• Expeditious preparation of (−)-2′-deoxy-3′-thiacytidine (3TC)
  作者：David C. Humber、Martin F. Jones、Jeremy J. Payne、Michael V.J. Ramsay、Boulos Zacharie、Haolun Jin、Arshad Siddiqui、Colleen A. Evans、H.L.Allan Tse、Tarek S. Mansour

  DOI：10.1016/s0040-4039(00)61330-8

  日期：1992.8

  The title compound has been prepared in enantiomerically pure form in four steps from (+)-thiolactic acid.