(4S)-4-acetamido-5-[[(1S)-2-[[(1S)-1-[[(1S)-2-[[(1S)-4-amino-1-[[(1R)-2-(carboxymethylamino)-1-(nitrososulfanylmethyl)-2-oxo-ethyl]carbamoyl]-4-oxo-butyl]amino]-1-benzyl-2-oxo-ethyl]carbamoyl]-3-methyl-butyl]amino]-1-methyl-2-oxo-ethyl]amino]-5-oxo-pentanoic acid

• 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
• 英文名称: (4S)-4-acetamido-5-[[(1S)-2-[[(1S)-1-[[(1S)-2-[[(1S)-4-amino-1-[[(1R)-2-(carboxymethylamino)-1-(nitrososulfanylmethyl)-2-oxo-ethyl]carbamoyl]-4-oxo-butyl]amino]-1-benzyl-2-oxo-ethyl]carbamoyl]-3-methyl-butyl]amino]-1-methyl-2-oxo-ethyl]amino]-5-oxo-pentanoic acid
• 英文别名: (4S)-4-acetamido-5-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2R)-1-(carboxymethylamino)-3-nitrososulfanyl-1-oxopropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
• 化学式: C₃₅H₅₁N₉O₁₃S
• 分子量: 837.908
• InChiKey: OPLYHCUKCLVCHF-KTHKBMNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  58
• 可旋转键数：
  26
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  376
• 氢给体数：
  10
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  EALFQCG 在 盐酸 、 sodium nitrite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以86%的产率得到(4S)-4-acetamido-5-[[(1S)-2-[[(1S)-1-[[(1S)-2-[[(1S)-4-amino-1-[[(1R)-2-(carboxymethylamino)-1-(nitrososulfanylmethyl)-2-oxo-ethyl]carbamoyl]-4-oxo-butyl]amino]-1-benzyl-2-oxo-ethyl]carbamoyl]-3-methyl-butyl]amino]-1-methyl-2-oxo-ethyl]amino]-5-oxo-pentanoic acid
  参考文献：
  名称：

  S-Nitrosothiols as novel, reversible inhibitors of human rhinovirus 3C protease

  摘要：

  Human rhinovirus (HRV) 3C protease was inactivated by a series of S-nitrosothiols. These compounds exhibited different inhibitory activities in a time- and concentration-dependent manner with second-order rate constants (k(inact)/K-I) ranging from 131 to 5360 M-1 min(-1). The inactive enzyme could be re-activated by DTT, GSH and ascorbate, which indicated the inactivation mechanism was through an S-transnitrosylation process. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00420-0

文献信息

• Fluorophore-Labeled <i>S</i>-Nitrosothiols
  作者：Xinchao Chen、Zhong Wen、Ming Xian、Kun Wang、Niroshan Ramachandran、Xiaoping Tang、H. Bernhard Schlegel、Bulent Mutus、Peng George Wang

  DOI：10.1021/jo015658p

  日期：2001.9.1

  A series of fluorophore-labeled S-nitrosothiols were synthesized, and their fluorescence enhancements upon removal of the nitroso (NO) group were evaluated either by transnitrosation or by photolysis. It was shown that, with a suitable alkyl linker, the fluorescence intensity of dansyl-labeled S-nitrosothiols could be enhanced up to 30-fold. The observed fluorescence enhancement was attributed to the intramolecular energy transfer from fluorophore to the SNO moiety. Ab initio density functional theory (DFT) calculations indicated that the "overlap" between the SNO moiety and the dansyl ring is favored because of their stabilizing interaction, which was in turn affected by both the length of the alkyl linker and the rigidity of the sulfonamide unit. In addition, one of the dansyl-labeled S-nitrosothiols was used to explore the kinetics of S-nitrosothiol/thiol transnitrosation and was evaluated as a fluorescence probe of S-nitrosothiol-bound NO transfer in human umbilical vein endothelial cells.