N-乙酰基-S-丙基-L-半胱氨酸 | 14402-54-1

• 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: N-乙酰基-S-丙基-L-半胱氨酸
• 英文名称: N-acetyl-S-propyl-L-cysteine
• 英文别名: (2R)-2-acetamido-3-propylsulfanylpropanoic acid
• CAS: 14402-54-1
• 化学式: C₈H₁₅NO₃S
• 分子量: 205.278
• InChiKey: PSOKBYBSKZWNMI-ZETCQYMHSA-N

物化性质

• 熔点：
  88-90°C
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-乙酰基-S-丙基-L-半胱氨酸 在 N-甲基吗啉 、 盐酸 作用下， 以 四氢呋喃 、 乙醚 、 乙酸乙酯 为溶剂， 生成 N-[(2R)-4-chloro-3-oxo-1-propylsulfanylbutan-2-yl]acetamide
  参考文献：
  名称：

  The S -alkyl chain length as a determinant of the anti-leukemic activity of cysteine chloromethyl ketone compounds

  摘要：

  A series of cysteine chloromethyl ketone compounds with a systematic variation of the S-alkyl chain length have been synthesized in order to gauge the effect of the alkyl chain length on the cytotoxicity of these compounds against human acute lymphoblastic leukemia cells. Comparable activities were observed for compounds with S-alkyl chains ranging from pentyl to dodecyl, with the best being undecyl (IC50 = 1.7 mu M) and dodecyl (IC50 = 2.0 mu M) against B-lineage leukemia cells and hexyl (IC50 = 0.7 mu M) against T-lineage leukemia cells. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00047-0
• 作为产物：
  描述：

  N-乙酰-L-半胱氨酸 、 溴丙烷 在 氨 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 N-乙酰基-S-丙基-L-半胱氨酸
  参考文献：
  名称：

  The S -alkyl chain length as a determinant of the anti-leukemic activity of cysteine chloromethyl ketone compounds

  摘要：

  A series of cysteine chloromethyl ketone compounds with a systematic variation of the S-alkyl chain length have been synthesized in order to gauge the effect of the alkyl chain length on the cytotoxicity of these compounds against human acute lymphoblastic leukemia cells. Comparable activities were observed for compounds with S-alkyl chains ranging from pentyl to dodecyl, with the best being undecyl (IC50 = 1.7 mu M) and dodecyl (IC50 = 2.0 mu M) against B-lineage leukemia cells and hexyl (IC50 = 0.7 mu M) against T-lineage leukemia cells. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00047-0

文献信息

• Organosulfur compounds for the prevention and treatment of neurodegenerative diseases
  申请人：Ott David Michael

  公开号：US10118891B2

  公开（公告）日：2018-11-06

  Organosulfur compounds and compositions are disclosed which can be administered in order to provide protection from the formation of aldehyde-protein adducts, protein aggregates, and the resulting neuroinflammation. Various neurodegenerative diseases which are suitable for treatment using these compositions include Alzheimer's disease, senile dementia, Parkinson's disease, multiple sclerosis, Lewy body disease, peripheral neuropathy, spinal cord injury, traumatic brain injury, stroke and cerebral ischemia.

  本研究公开了有机硫化合物和组合物，使用这些化合物和组合物可以防止醛-蛋白质加合物、蛋白质聚集体的形成以及由此引起的神经炎症。适合使用这些组合物治疗的各种神经退行性疾病包括阿尔茨海默病、老年痴呆症、帕金森病、多发性硬化症、路易体病、周围神经病变、脊髓损伤、脑外伤、中风和脑缺血。
• Method of decreasing protein-aldehyde adducts by administering a mixed disulfide of n-acetylcysteine and propyl mercaptan, propenyl mercaptan, or allyl mercaptan
  申请人：Ott David Michael

  公开号：US10758498B2

  公开（公告）日：2020-09-01

  Divalent salts of S-allylmercapto-N-acetylcysteine and related compositions are disclosed which can be administered in order to provide protection from the formation of aldehyde-protein adducts, protein carbonylation, protein aggregation, and the resulting neuroinflammation. Various neurodegenerative diseases which are suitable for treatment using these compositions include Alzheimer's disease, senile dementia, Parkinson's disease, multiple sclerosis, Lewy body disease, peripheral neuropathy, spinal cord injury, stroke and cerebral ischemia.

  本发明公开了 S-烯丙基巯基-N-乙酰半胱氨酸的二价盐及相关组合物，使用这些组合物可以防止醛蛋白加合物的形成、蛋白质羰基化、蛋白质聚集以及由此引起的神经炎症。适合使用这些组合物治疗的各种神经退行性疾病包括阿尔茨海默病、老年痴呆症、帕金森病、多发性硬化症、路易体病、周围神经病变、脊髓损伤、中风和脑缺血。
• Über Alliin, die genuine Muttersubstanz des Knoblauchöls. 1. Mitteilung über Allium-Substanzen
  作者：Arthur Stoll、Ewald Seebeck

  DOI：10.1002/hlca.19480310140

  日期：——
• Acylase I-Catalyzed Deacetylation of <i>N</i>-Acetyl-<scp>l</scp>-cysteine and <i>S</i>-Alkyl-<i>N</i>-acetyl-<scp>l</scp>-cysteines
  作者：Vinita Uttamsingh、D. A. Keller、M. W. Anders

  DOI：10.1021/tx980018b

  日期：1998.7.1

  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.
• Grenby; Young, Biochemical Journal, 1959, vol. 71, p. 25P
  作者：Grenby、Young

  DOI：——

  日期：——