S-叔丁基-L-半胱氨酸叔丁酯 | 45157-84-4

• 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
• 中文名称: S-叔丁基-L-半胱氨酸叔丁酯
• 英文名称: S-tert.-Butyl-L-cystein-tert.-butylester
• 英文别名: tert-butyl (2R)-2-amino-3-(tert-butylsulfanyl)propanoate；tert-butyl (2R)-2-amino-3-tert-butylsulfanylpropanoate
• CAS: 45157-84-4
• 化学式: C₁₁H₂₃NO₂S
• 分子量: 233.375
• InChiKey: LYGGEHGWPZTHJD-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  77.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  S-叔丁基-L-半胱氨酸叔丁酯 在 三氟乙酸 作用下， 生成 D-S-叔丁基半胱氨酸
  参考文献：
  名称：

  Beyerman,H.C.; Bontekoe,J.S., Recueil des Travaux Chimiques des Pays-Bas, 1962, vol. 81, p. 691 - 698

  摘要：

  DOI：
• 作为产物：
  描述：

  N-叔丁氧羰基-S-叔丁基-L-半胱氨酸 在 吡啶 、 4-二甲氨基吡啶 、 对甲苯磺酸 、 N,N-二甲基-1,3-二氨基丙烷 作用下， 以 乙腈 为溶剂， 反应 19.25h， 生成 S-叔丁基-L-半胱氨酸叔丁酯
  参考文献：
  名称：

  Pozdnev, V. F., Journal of general chemistry of the USSR, 1988, vol. 58, # 3, p. 592 - 597

  摘要：

  DOI：

文献信息

• 丹参素与H2S/NO供体结合物及其制备方法和在制药中的应用
  申请人：复旦大学

  公开号：CN111484413A

  公开（公告）日：2020-08-04

  本发明属化学制药领域，涉及中草药丹参中有效成分丹参素与H 2 S/NO供体的结合物及其制备方法和在制药中的应用，尤其是在制备防治心脑血管和炎症相关疾病药物中的用途。本发明通过体外氧化应激损伤和炎症模型实验，结果显示所述的结合物能显著抑制H 2 O 2 诱导的SH‑SY5Y细胞氧化应激损伤，对损伤细胞具有明显的保护作用；能显著抑制内毒素(LPS)诱导的小鼠腹腔巨噬细胞分泌炎性介质，减少炎症诱导的一氧化氮和炎性细胞因子的释放；体内活性实验结果显示，所述的结合物对LPS诱导的小鼠腹膜炎能改善小鼠的凝血时间，明显抑制小鼠腹腔的炎性细胞因子的释放，结果表明所述化合物可用于制备防治心脑血管疾病和炎症性疾病的药物。
• Stereoselective synthesis of novel N-(α-l-arabinofuranos-1-yl)-l-amino acids
  作者：Ming Zhao、Yuji Wang、Caixia Huo、Chunyu Li、Xiaoyi Zhang、Li Peng、Shiqi Peng

  DOI：10.1016/j.tetasy.2009.01.014

  日期：2009.2

  were converted to α- and β-anomers of N-(2,3,5-tri-O-acetyl-l-arabinofuranosyl)-N-(2-nitrobenzenesulfonyl)-l-amino acids, 3a–f-α and 3a–f-β, in 87–92% yields. While in the presence of NaOCH3, 3a–f-α and 3a–f-β were converted to α- and β-anomers of N-(l-arabinofuranosyl)-N-(2-nitrobenzenesulfonyl)-l-amino acids, 4a–f-α and 4a–f-β, in 90–96% yields. Treating 4a–f-α and 4a–f-β with N-ethyldiisopropylamine

  在铅解毒中，N-糖基-1-氨基酸的α-端基异构体比其β-端基异构体更有效。这里报道了用于立体选择性地制备N-（α-1-阿拉伯糖-1-基）-1-氨基酸的六步反应路线。用乙酸酐和乙酸钠处理1-阿拉伯糖，得到90％产率的1,2,3,5-四-O-乙酰基-1-阿拉伯呋喃糖。除去1-乙酰基后，将由此形成的2,3,5-三-O-乙酰基-1-阿拉伯呋喃糖和N-（2-硝基苯基磺酰基）-1-氨基酸叔丁基酯用三苯基膦处理以进行Mitsunobu脱水并形成2,3,5-三-O-乙酰基-1-阿拉伯呋喃糖基-1- [ N-（2-硝基苯基磺酰基）]氨基酸叔丁基酯2a-f，其α-与β-端基异构体的比例为8/1至9/1。色谱分离提供差向异构纯2a–f-α和2a–f-β。在存在CF 3 CO 2 H的情况下，2a–f-α和2a–f-β转化为N-（2,3,5-三-O-乙酰基-1-阿拉伯呋喃糖基）的α-和β-异头物。- ñ - （2
• Acid-Labile Protecting Groups for the Synthesis of Lipidated Peptides
  作者：Dieter Kadereit、Patrick Deck、Ines Heinemann、Herbert Waldmann

  DOI：10.1002/1521-3765(20010316)7:6<1184::aid-chem1184>3.0.co;2-5

  日期：2001.3.16

  Lipidated peptides and their neolipoprotein derivatives are efficient tools for the investigation of biological processes in molecular detail. These compounds are often acid- and base-labile, and their synthesis requires the use of a combination of blocking groups that can be removed under very mild conditions. In this article we demonstrate that the Boc urethane and different trityl-type protecting groups

  脂质肽及其新脂蛋白衍生物是用于详细研究分子生物学过程的有效工具。这些化合物通常对酸和碱不稳定，并且它们的合成需要使用可以在非常温和的条件下除去的保护基团的组合。在本文中，我们证明了Boc氨基甲酸酯和不同的三苯甲基型保护基可以在足够温和以适应脂肽合成需求的酸性条件下选择性裂解。因此，在二甲基吡啶存在的情况下，Boc基团被TMS三氟甲磺酸酯裂解，在三乙基硅烷作为阳离子清除剂的情况下，在二氯甲烷中用1％TFA除去甲基三苯甲基（Mtt）和甲氧基三苯甲基（Mmt）基团。
• Therapeutic effect and mechanism study of L-cysteine derivative 5P39 on LPS-induced acute lung injury in mice
  作者：Yanting He、Yalei Zhao、Yuchen Feng、Anqi Ren、Yunyi Zhang、Yang Wang、Hong Li

  DOI：10.1016/j.ejphar.2019.172893

  日期：2020.2

  Organosulfur compounds, such as L-cysteine, allicin and other sulfur-containing organic compounds in Allium species, have been proposed to possess many important physiological and pharmacological functions. A novel L-cysteine derivative, t-Butyl S-allylthio-L-cysteinate (5P39), was designed and synthesized by combining L-cysteine derivative and allicin pharmacophore through a disulfide bond. This study aimed to explore the effects and mechanisms of 5P39 on lipopolysaccharide (LPS)-induced acute lung injury (ALI) in mice. At the experimental concentration (5, 10 and 20 mu M), 5P39 suppressed the excessive secretion of nitric oxide (NO) and interleukin-6 (IL-6) in mice peritoneal macrophages stimulated by LPS. A mouse model of ALI was established by tracheal instillation of LPS for 2 h before 5P39 (30 and 60 mg/kg) administration. The results showed that 5P39 treatment down-regulated the wet/dry weight ratio (W/D ratio) of lungs and reduced the protein concentration, the number of total cells as well as the myeloperoxidase (MPO) activity in bronchoalveolar lavage fluid (BALF). 5P39 administration improved the histopathological changes of lungs in ALI mice with the decreased levels of pro-inflammatory cytokines in BALF. The inhibitory effects of 5P39 on the toll-like receptor 4 (TLR4) expression and macrophages accumulation in lung tissues were observed by immunohistochemistry. Additionally, 5P39 significantly attenuated the LPS-activated high expression of key proteins in TLR4/MyD88 signaling pathway. Taken together, the present study showed that 5P39 effectively alleviate the severity of ALI, and its mechanism might relate to the inhibition of LPS-activated TLR4/MyD88 signaling pathway, demonstrating a promising potential for further development into an anti-inflammatory drug candidate.
• <b>The Tertiary Butyl Group as a Blocking Agent for Hydroxyl, Sulfhydryl and Amido Functions in Peptide Synthesis</b>
  作者：Francis M. Callahan、George W. Anderson、Rolf. Paul、Joan E. Zimmerman

  DOI：10.1021/ja00885a020

  日期：1963.1