(2S)-2-mercapto-3-methylbutyric acid | 114423-53-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S)-2-mercapto-3-methylbutyric acid
• 英文别名: (S)-2-mercapto-3-methylbutanoic acid；(S)-2-sulfanyl-3-methylbutanoic acid；(2S)-3-methyl-2-sulfanylbutanoic acid
• CAS: 114423-53-9
• 化学式: C₅H₁₀O₂S
• 分子量: 134.199
• InChiKey: MTMDLUFMACHNQR-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-mercapto-3-methylbutyric acid 在 lithium aluminium tetrahydride 、 碳酸氢钠 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 2.0h， 生成 (2S)-3-methyl-2-(pyridin-2-yldisulfanyl)butan-1-ol
  参考文献：
  名称：

  [EN] PBD CONJUGATES FOR TREATING DISEASES
  [FR] CONJUGUÉS DE PBD POUR LE TRAITEMENT DE MALADIES

  摘要：

  本公开涉及吡咯并苯二氮卓（PBD）前药及其共轭物。本公开还涉及所述共轭物的药物组合物，以及制造和使用它们的方法。

  公开号：

  WO2017172930A1
• 作为产物：
  描述：

  D-缬氨酸 在 氢溴酸 、 一水合肼 、 potassium bromide 、 sodium nitrite 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 (2S)-2-mercapto-3-methylbutyric acid
  参考文献：
  名称：

  与体外展示兼容的骨架环肽的核糖体合成

  摘要：

  骨架环肽是治疗开发的一个有吸引力的类别。然而，结合核糖体合成的体外展示技术本质上不适用于此类“表型”，因为与“基因型”相关的 C 端肽区域丢失。在这里，我们报告了一种能够展示骨架环肽的方法。为了实现这一目标，利用遗传密码重编程来实施重排策略，包括将包含噻唑烷保护的半胱氨酸和 2-氯乙酰胺 (ClAc) 侧链的设计启动子的核糖体掺入，然后是下游位置的 α-硫代酸和半胱氨酸. 线性肽表达后，α-硫酯和半胱氨酸的硫醇基团之间发生自发的硫酯重排，释放 α-硫代基团并导致与上游 ClAc 侧链基团的交联。然后噻唑烷保护的半胱氨酸的选择性脱保护立即促进分子内天然化学连接，如各种序列和环大小所示。在这种方法中，骨架环肽通过侧链硫醚共价键保留其 C 端肽区域，使其与体外展示兼容。

  DOI：

  10.1021/jacs.8b05327

文献信息

• Ruthenium(II)–Arene Thiocarboxylates: Identification of a Stable Dimer Selectively Cytotoxic to Invasive Breast Cancer Cells
  作者：Liam J. Stephens、Aviva Levina、Iman Trinh、Victoria L. Blair、Melissa V. Werrett、Peter A. Lay、Philip C. Andrews

  DOI：10.1002/cbic.201900676

  日期：2020.4.17

  RuII -arene complexes provide a versatile scaffold for novel anticancer drugs. Seven new RuII -arene-thiocarboxylato dimers were synthesized and characterized. Three of the complexes (2 a, b and 5) showed promising antiproliferative activities in MDA-MB-231 (human invasive breast cancer) cells, and were further tested in a panel of fifteen cancerous and noncancerous cell lines. Complex 5 showed moderate

  RuII-芳烃配合物为新型抗癌药物提供了多功能支架。合成并表征了七个新的RuII-芳烃-硫代羧酰二聚体。三种复合物（2a，b和5）在MDA-MB-231（人类浸润性乳腺癌）细胞中显示出有希望的抗增殖活性，并在一组15种癌性和非癌性细胞系中进行了进一步测试。复合物5在MDA-MB-231细胞中表现出中等但显着的选择性活性（IC50 = 39±4μmRu）。实时增殖研究表明5诱导了MDA-MB-231细胞凋亡，但对A549（人肺癌，上皮）细胞无影响。相比之下，2 a和b在这两种细胞系中均显示出中等的抗增殖活性，但没有凋亡。侵袭性细胞的选择性细胞毒性为5，
• METHODS FOR TREATING BLOOD DISORDERS
  申请人：Perrine P. Susan

  公开号：US20080075692A1

  公开（公告）日：2008-03-27

  Methods of treating blood disorders are described.

  描述了治疗血液疾病的方法。
• Synthesis and renin inhibitory activity of angiotensinogen analogs having dehydrostatine, Lue.psi.[CH2S]Val, or Lue.psi.[CH2SO] Val at the Pt, P1' cleavage site
  作者：Clark W. Smith、Hossain H. Saneii、Tomi K. Sawyer、Donald T. Pals、Terrence A. Scahill、Bharat V. Kamdar、Judy A. Lawson

  DOI：10.1021/jm00402a022

  日期：1988.7

  The synthesis and in vitro renin inhibitory potencies of angiotensinogen (ANG) analogues having amide (CONH) bond replacements at P1-P1', the Leu-Val cleavage site, corresponding to Leu psi[CH2SO]Val, and the trans olefinic analogue of statine (Sta), 4(S)-amino-6-methyl-2(E)-heptenoic acid (dehydrostatine, Dhs), are reported. These are compared to P1-P1' Leu psi[CH2NH]Val-, Sta-, or Phe-Phe-substituted analogues of the same template. The Dhs pseudodipeptide was found to be an adequate mimic of a trans CONH bond and gave a peptide, H-Pro-His-Pro-Phe-His-Dhs-Ile-His-D-Lys-OH, approximately equal in potency to a Phe-Phe-containing inhibitor, but 200-fold less potent than its Sta-substituted congener. That the enhanced potency of the Sta-containing peptide most likely depends on hydrogen bonding as well as tetrahedral geometry is indicated by the 50-100-fold lower potency of the tetrahedral Leu psi[CH2S]Val and Leu psi[CH2SO]Val analogues as compared to the Leu psi[CH2NH]Val-containing congener.
• Synthesis and inhibitory activity of substrate-analog fructosyl peptide oxidase inhibitors
  作者：Bunta Watanabe、Atsushi Ichiyanagi、Kozo Hirokawa、Keiko Gomi、Toru Nakatsu、Hiroaki Kato、Naoki Kajiyama

  DOI：10.1016/j.bmcl.2015.07.045

  日期：2015.9

  Fructosyl peptide oxidases (FPOXs) play a crucial role in the diagnosis of diabetes. Their main function is to cleave fructosyl amino acids or fructosyl peptides into glucosone and the corresponding amino acids/dipeptides. In this study, the substrate-analog FPOX inhibitors 1a-c were successfully designed and synthesized. These inhibitors mimic N-alpha-fructosyl-L-valine (Fru-Val), [N-alpha-fructosyl-L-valyl]-L-histidine (Fru-ValHis), and N-epsilon-fructosyl-L-lysine (epsilon Fru-Lys), respectively. The secondary nitrogen atom in the natural substrates, linking fructose and amino acid or dipeptide moieties, was substituted in 1a-c with a sulfur atom to avoid enzymatic cleavage. Kinetic studies revealed that 1a-c act as competitive inhibitors against an FPOX obtained from Coniochaeta sp., and K-i values of 11.1, 66.8, and 782 mu M were obtained for 1a-c, respectively. (C) 2015 Elsevier Ltd. All rights reserved.
• SMITH, CLARK W.;SANEII, HOSSAIN H.;SAWYER, TOMI K.;PALS, DONALD T.;SCAHIL+, J. MED. CHEM., 31,(1988) N 7, 1377-1382
  作者：SMITH, CLARK W.、SANEII, HOSSAIN H.、SAWYER, TOMI K.、PALS, DONALD T.、SCAHIL+

  DOI：——

  日期：——