S-丁基-D-半胱氨酸 | 4134-56-9

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 半胱氨酸类衍生物
• 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-丁基-D-半胱氨酸
• 中文别名: (R)-2-氨基-3-(丁基硫)丙酸
• 英文名称: S-butyl-L-cysteine
• 英文别名: S-Butyl-L-cystein；(2R)-2-azaniumyl-3-butylsulfanylpropanoate
• CAS: 4134-56-9
• 化学式: C₇H₁₅NO₂S
• 分子量: 177.268
• InChiKey: FFGXHYXBEDRCNM-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  88.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  S-丁基-D-半胱氨酸 在 ammonium hydroxide 、 sodium hydroxide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 2.0h， 生成 (2R)-2-[(2-benzyl-3-sulfanylpropanoyl)amino]-3-butylsulfanylpropanoic acid
  参考文献：
  名称：

  Sulfur-containing acylamino acids. I. Syntheses and angiotensin I converting enzyme-inhibitory activities of sulfur-containing N-mercaptoalkanoyl amino acids.

  摘要：

  含硫氨基酸的N-巯基烷酰基衍生物被合成并检验了它们对从兔肺提取的血管紧张素I转化酶（ACE）的抑制作用。ACE的抑制作用是通过采用高脯酰-L-组氨酰-L-亮氨酸作为底物的光谱测定法确定的。在合成的含硫化合物中，N-(2-苄基-3-巯基丙酰基)-S-甲基-L-半胱氨酸（13a）和N-(2-苄基-3-巯基丙酰基)-S-乙基-L-半胱氨酸（13c）对ACE活性显示了最强大的抑制作用。13a和13c对ACE活性的IC50值分别为0.028和0.020 μM。

  DOI：

  10.1248/cpb.35.2382
• 作为产物：
  描述：

  S-n-Butyl-N-acetyl-L-cysteine 在 pig kidney acylase I 作用下， 以 phosphate buffer 为溶剂， 反应 0.17h， 生成 S-丁基-D-半胱氨酸
  参考文献：
  名称：

  Acylase I-Catalyzed Deacetylation of N-Acetyl-l-cysteine and S-Alkyl-N-acetyl-l-cysteines

  摘要：

  The aminoacylase that catalyzes the hydrolysis of N-acetyl-L-cysteine (NAC) was identified as acylase I after purification by column chromatography and electrophoretic analysis. Rat kidney cytosol was fractionated by ammonium sulfate precipitation, and the proteins were separated by ion-exchange column chromatography, gel-filtration column chromatography, and hydrophobic interaction column chromatography. Acylase activity with NAC and N-acetyl-L-methionine (NAM), a known substrate for acylase I, as substrates coeluted during all chromatographic steps. Sodium dodecyl sulfate-polyacrylamide gel electrophoresis showed that the protein was purified to near homogeneity and had a subunit M-r of 43 000, which is identical with the M-r of acylase I from porcine kidney and bovine liver. n-Butylmalonic acid was a slow-binding inhibitor of acylase I and inhibited the deacetylation of NAC with a K-i of 192 +/- 27 mu M These results show that acylase I catalyzes the deacetylation of NAG. The acylase I-catalyzed deacetylation of a range of S-alkyl-N-acetyl-L-cysteines, their carbon and oxygen analogues, and the selenium analogue of NAM was also studied with porcine kidney acylase I. The specific activity of the acylase I-catalyzed deacetylation of these substrates was related to their calculated molar volumes and lag P values. The S-alkyl-N-acetyl-L-cysteines with short (C-0-C-3) and unbranched S-alkyl substituents were good acylase I substrates, whereas the S-alkyl-N-acetyl-L-cysteines with long (>C-3) and branched S-alkyl substituents were poor acylase I substrates. The carbon and oxygen analogues of S-methyl-N-acetyl-L-cysteine and the carbon analogue of S-ethyl-N-acetyl-L-cysteine were poor acylase I substrates, whereas the selenium analogue of NAM was a good acylase I substrate.

  DOI：

  10.1021/tx980018b

文献信息

• Efficient S-alkylation of cysteine in the presence of 1,1,3,3-tetramethylguanidine
  作者：Marek Włostowski、Sylwia Czarnocka、Piotr Maciejewski

  DOI：10.1016/j.tetlet.2010.08.097

  日期：2010.11

  The synthesis of S-alkylated cysteine derivatives was carried out successfully in the presence of 1,1,3,3-tetramethylguanidine. Alkylation proceeded in high yields on unprotected amino acids and peptides containing a sulfhydryl group.

  在1,1,3,3-四甲基胍的存在下成功进行了S-烷基化的半胱氨酸衍生物的合成。在未保护的氨基酸和含有巯基的肽上，烷基化反应高收率地进行。
• USE OF ALLYLCYSTEINE OR ITS ANALOGS AND PHARMACEUTICAL COMPOSITION THREROF
  申请人：Fudan University

  公开号：EP2186512A1

  公开（公告）日：2010-05-19

  The invention discloses a use of compound S-allyl cysteine or its analogues in preparation of medicaments for preventing or treating myocardial injury and a preparation method thereof, as well as a pharmaceutical composition comprising the compound.

  该发明揭示了利用复合S-烯丙基半胱氨酸或其类似物制备用于预防或治疗心肌损伤的药物以及其制备方法，以及包含该化合物的药物组合物。
• [EN] ALPHA-HELICAL MIMETICS<br/>[FR] MIMÉTIQUES D'HÉLICE ALPHA
  申请人：EARCH THE WALTER AND ELIZA HAL

  公开号：WO2006002474A1

  公开（公告）日：2006-01-12

  Benzoyl urea derivatives that are alpha helical peptide mimetics that mimic BH3-only proteins, compositions containing them, their conjugation to cell-targeting moieties, and their use in the regulation of cell death are disclosed. The benzoyl urea derivatives are capable of binding to and neutralising pro-survival Bcl-2 proteins. Use of the benzoyl urea derivatives in the treatment and/or prophylaxis of diseases or conditions associated with deregulation of cell death are also disclosed.

  本文揭示了α螺旋肽类似物的苯甲酰脲衍生物，这些类似物模拟BH3-only蛋白质，包含它们的组合物，它们与细胞靶向基团的结合，以及它们在调控细胞死亡中的用途。苯甲酰脲衍生物能够结合并中和促生存的Bcl-2蛋白。还揭示了苯甲酰脲衍生物在治疗和/或预防与细胞死亡失调相关的疾病或症状中的用途。
• Method Of Synthesizing S-Allyl-Cysteine Analogues And Their Therapeutic Application In Treating Myocardial Infarction
  申请人：ZHU YIZHUN

  公开号：US20090036534A1

  公开（公告）日：2009-02-05

  A pharmaceutical composition and methods of producing and application of the composition for treating myocardial infarction of a subject are disclosed. The pharmaceutical composition comprises a therapeutically effective amount of at least one synthesized compound selected from the group consisting of SEC, SPC, SBC, SPEC, SAC, SAMC, and SPRC, and a pharmaceutically acceptable carrier.

  揭示了一种用于治疗受试者心肌梗死的药物组合物及其制备和应用方法。该药物组合物包括从SEC、SPC、SBC、SPEC、SAC、SAMC和SPRC等化合物组合中选择的至少一种合成化合物的治疗有效量，以及一种药用可接受的载体。
• Subtype-Specific Agonists for NMDA Receptor Glycine Binding Sites
  作者：Alex R. Maolanon、Rune Risgaard、Shuang-Yan Wang、Yoran Snoep、Athanasios Papangelis、Feng Yi、David Holley、Anne F. Barslund、Niels Svenstrup、Kasper B. Hansen、Rasmus P. Clausen

  DOI：10.1021/acschemneuro.7b00117

  日期：2017.8.16

  superagonists at the GluN1 subunit with agonist efficacies of 398% and 308% compared to glycine. This study demonstrates that subunit-selectivity among glycine site NMDA receptor agonists can be achieved and suggests that glycine-site agonists can be developed as pharmacological tool compounds to study GluN2C-specific effects in NMDA receptor-mediated neurotransmission.

  设计了一系列基于丝氨酸为先导结构的类似物，并使用两电极电压钳（TEVC）电生理学对重组NMDA受体亚型（GluN1 / 2A-D）的激动剂活性进行了评估。以依赖于NMDA受体中的GluN2亚基的方式观察到亚基选择性，效力和激动剂功效的明显变化。特别是化合物15a和16a是在GluN1亚基上有效的GluN2C特异性超激动剂，与甘氨酸相比，激动剂的效率为398％和308％。这项研究表明，可以实现甘氨酸位点NMDA受体激动剂之间的亚基选择性，并建议可以开发出甘氨酸位点的激动剂作为药理工具化合物，以研究NMDA受体介导的神经传递中GluN2C的特异性作用。