(2S)-2-({[(2-甲基-2-丙基)氧基]羰基}氨基)硫代丙S-酸 | 80354-38-7

• 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: (2S)-2-({[(2-甲基-2-丙基)氧基]羰基}氨基)硫代丙S-酸
• 英文名称: Boc-Ala-SH
• 英文别名: (S)-2-[(tert-Butyloxycarbonyl)amino]propanethioic acid；(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanethioic S-acid
• CAS: 80354-38-7
• 化学式: C₈H₁₅NO₃S
• 分子量: 205.278
• InChiKey: XOUNMZDIMUZMTD-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  56.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-2-({[(2-甲基-2-丙基)氧基]羰基}氨基)硫代丙S-酸 在 碘 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以0.82 g的产率得到(S)-2-((tert-butoxycarbonyl)amino)propanoic dithioperoxyanhydride
  参考文献：
  名称：

  Thioacetic Acid/NaSH-Mediated Synthesis of N-Protected Amino Thioacids and Their Utility in Peptide Synthesis

  摘要：

  Thioacids are recently gaining momentum due to their versatile reactivity. The reactivity of thioacids has been widely explored in the selective amide/peptide bond formation. Thioacids are generally synthesized from the reaction between activated carboxylic acids such as acid chlorides, active esters, etc., and Na2S, H2S, or NaSH. We sought to investigate whether the versatile reactivity of the thioacids can be tuned for the conversion of carboxylic acids into corresponding thioacids in the presence of NaSH. Herein, we report that thioacetic acid- and NaSH-mediated synthesis of N-protected amino thioacids from the corresponding N-protected amino acids, oxidative dimerization of thioacids, crystal conformations of thioacid oxidative dimers, and the utility of thioacids and oxidative dimers in peptide synthesis. Our results suggest that peptides can be synthesized without using standard coupling agents.

  DOI：

  10.1021/jo402872p
• 作为产物：
  描述：

  N-叔丁氧羰基-L-丙氨酸 在 盐酸 N-甲基吗啉 、 硫化氢 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 生成 (2S)-2-({[(2-甲基-2-丙基)氧基]羰基}氨基)硫代丙S-酸
  参考文献：
  名称：

  9- [2-（膦酰基甲氧基）乙基]腺嘌呤（PMEA）的新型双（L-氨基酸）酯前药的设计与合成，具有改善的抗HBV活性。

  摘要：

  合成了一系列新型的9- [2-（膦酰基甲氧基）乙基]腺嘌呤（PMEA）双（L-氨基酸）酯前药，并在HepG 2 2.2.15细胞中评估了它们的抗HBV活性。与用作阳性对照的阿德福韦酯相比，化合物11、12、21、22、26和27表现出更强的抗HBV活性和更高的选择性指数（SI）。被发现是最有效的化合物11，其效力是阿德福韦酯的5倍，EC50值为0.095 microM，CC50值为6636 microM。化合物11的SI值（> 69,000）分别比阿德福韦酯和拉米夫定高60倍和24倍。体外稳定性研究表明，化合物11比阿德福韦酯更稳定，t1 / 2为270分钟。

  DOI：

  10.1016/j.bmcl.2006.10.021

文献信息

• Design and synthesis of novel bis(l-amino acid) ester prodrugs of 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA) with improved anti-HBV activity
  作者：Xiaozhong Fu、Saihong Jiang、Chuan Li、Jian Xin、Yushe Yang、Ruyun Ji

  DOI：10.1016/j.bmcl.2006.10.021

  日期：2007.1

  A series of novel bis(L-amino acid) ester prodrugs of 9-[2-(phosphonomethoxy)ethyl] adenine (PMEA) was synthesized and their anti-HBV activity was evaluated in HepG 2 2.2.15 cells. Compounds 11, 12, 21, 22, 26, and 27 demonstrated more potent anti-HBV activity and higher selective index (SI) than adefovir dipivoxil, which was used as a positive control. Compound 11, which was found to be the most potent

  合成了一系列新型的9- [2-（膦酰基甲氧基）乙基]腺嘌呤（PMEA）双（L-氨基酸）酯前药，并在HepG 2 2.2.15细胞中评估了它们的抗HBV活性。与用作阳性对照的阿德福韦酯相比，化合物11、12、21、22、26和27表现出更强的抗HBV活性和更高的选择性指数（SI）。被发现是最有效的化合物11，其效力是阿德福韦酯的5倍，EC50值为0.095 microM，CC50值为6636 microM。化合物11的SI值（> 69,000）分别比阿德福韦酯和拉米夫定高60倍和24倍。体外稳定性研究表明，化合物11比阿德福韦酯更稳定，t1 / 2为270分钟。
• Ynamide-Mediated Thiopeptide Synthesis
  作者：Jinhua Yang、Changliu Wang、Silin Xu、Junfeng Zhao

  DOI：10.1002/anie.201811586

  日期：2019.1.28

  two‐step strategy for thiopeptide bond formation with readily available monothiocarboxylic acids as thioacyl donors is described. The α‐thioacyloxyenamide intermediates formed from the ynamides and monothiocarboxylic acids can be purified, characterized, and stored. The balance between their activity and stability enables them to act as effective thioacylating reagents to afford thiopeptide bonds under mild

  不足的合成策略不足以将硫酰胺键位点引入肽主链，因此无法探索作为肽和蛋白质化学生物学工具的硫酰胺替代物的全部潜力。描述了一种新颖的由酰胺介导的两步策略，用于以易于获得的单硫代羧酸作为硫代酰基供体的硫肽键形成。由乙酰胺和一硫代羧酸形成的α-硫代酰氧烯酰胺中间体可以进行纯化，表征和储存。它们的活性和稳定性之间的平衡使它们能够充当有效的硫酰化试剂，在温和的反应条件下提供硫肽键。氨基酸官能团，例如OH，CONH 2，并且在巯基肽合成过程中不需要保护吲哚NH基团。这种策略的模块化性质使得在溶液和固相中都可以将硫酰胺键定点结合到肽主链中。
• T3P (propylphosphonic anhydride) mediated conversion of Nα-protected amino/peptide acids into thioacids
  作者：Chilakapati Madhu、Basavaprabhu、T.M. Vishwanatha、Vommina V. Sureshbabu

  DOI：10.1016/j.tetlet.2012.01.027

  日期：2012.3

  protocol, which makes use of T3P as an acid activator for the synthesis of Nα-protected amino/peptide thioacids from corresponding acids in the presence of finely ground Na2S as hydrosulfide ion donor is described. The protocol employed significantly increases the overall efficiency as the yield, reaction duration and purity of even sterically hindered amino acids.

  一般，轻度和高效的协议，这使得使用T3P作为酸活化剂用于合成Ñ α -保护的氨基/肽硫代酸在精细研磨的Na的存在相应的酸2为氢硫化物离子供体被描述S上。所采用的方案显着提高了整体效率，因为即使是位阻氨基酸也可以提高收率，反应持续时间和纯度。
• AMINOACYL PRODRUGS
  申请人：Lerchen Hans-Georg

  公开号：US20100273789A1

  公开（公告）日：2010-10-28

  The present application relates to prodrug derivatives of 5-chloro-N-((5S)-2-oxo-3-[2-fluoro-4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide, processes for their preparation, their use for the treatment and/or prophylaxis of diseases, and their use for the manufacture of medicaments for the treatment and/or prophylaxis of diseases, especially of thromboembolic disorders.

  本申请涉及5-氯-N-((5S)-2-氧代-3-[2-氟-4-(3-氧代吗啉-4-基)苯基]-1,3-噁唑烷-5-基}甲基)噻吩-2-羧酰胺的前药衍生物，其制备方法，它们用于治疗和/或预防疾病，以及它们用于制造用于治疗和/或预防疾病的药物，特别是用于治疗和/或预防血栓栓塞性疾病。
• Aminoacyl prodrug derivatives and medicaments for treatment of thromboembolic disorders
  申请人：Lerchen Hans-Georg

  公开号：US20100292230A1

  公开（公告）日：2010-11-18

  The present application relates to prodrug derivatives of 5-chloro-N-((5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide, processes for their preparation, their use for the treatment and/or prophylaxis of diseases, and their use for the manufacture of medicaments for the treatment and/or prophylaxis of diseases, especially of thromboembolic disorders.

  本申请涉及5-氯-N-((5S)-2-氧代-3-[4-(3-氧代吗啡啉-4-基)苯基]-1,3-噁唑烷-5-基}甲基)噻吩-2-羧酰胺的前药衍生物，其制备方法，它们用于治疗和/或预防疾病，以及它们用于制造用于治疗和/或预防疾病的药物，特别是用于治疗和/或预防血栓栓塞性疾病。