H-Gly-Ile-Cys-Pro-Leu-Cys(Acm)-Met(O)-OH | 169061-90-9

• 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: H-Gly-Ile-Cys-Pro-Leu-Cys(Acm)-Met(O)-OH
• 英文别名: (2S)-2-[[(2R)-3-(acetamidomethylsulfanyl)-2-[[(2S)-2-[[(2S)-1-[(2R)-2-[[(2S,3S)-2-[(2-aminoacetyl)amino]-3-methylpentanoyl]amino]-3-sulfanylpropanoyl]pyrrolidine-2-carbonyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-4-methylsulfinylbutanoic acid
• CAS: 169061-90-9
• 化学式: C₃₃H₅₈N₈O₁₀S₃
• 分子量: 823.069
• InChiKey: NGLFPRQNERHXBG-HVCKAPCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  54
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  321
• 氢给体数：
  9
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  H-Gly-Ile-Cys-Pro-Leu-Cys(Acm)-Met(O)-OH 在 碘化铵 、 二甲基硫 作用下， 以 三氟乙酸 为溶剂， 反应 1.0h， 生成 (S³-S^3')-2
  参考文献：
  名称：

  Reduction of methionine sulfoxide with : Compatibility with peptides containing cysteine and aromatic amino acids

  摘要：

  The reduction of methionine sulfoxide with ammonium iodide in trifluoroacetic acid has been studied in peptides containing cysteine, histidine, tyrosine or tryptophan residues. While histidine and tyrosine have proved to be stable under the experimental conditions, cysteine is oxidized to cystine and tryptophan dimerizes to form 2-indolylindolenine derivatives. The use of methyl sulfide to increase the reduction rate minimizes the problem and protection of indole ring with the formyl group avoids the side reaction for this amino acid. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00954-5
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 H-Gly-Ile-Cys-Pro-Leu-Cys(Acm)-Met(O)-OH
  参考文献：
  名称：

  Reduction of methionine sulfoxide with : Compatibility with peptides containing cysteine and aromatic amino acids

  摘要：

  The reduction of methionine sulfoxide with ammonium iodide in trifluoroacetic acid has been studied in peptides containing cysteine, histidine, tyrosine or tryptophan residues. While histidine and tyrosine have proved to be stable under the experimental conditions, cysteine is oxidized to cystine and tryptophan dimerizes to form 2-indolylindolenine derivatives. The use of methyl sulfide to increase the reduction rate minimizes the problem and protection of indole ring with the formyl group avoids the side reaction for this amino acid. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00954-5

文献信息

• A study of the use of NH4I for the reduction of methionine sulfoxide in peptides containing cysteine and cystine
  作者：Ernesto Nicolás、Marta Vilaseca、Ernest Giralt

  DOI：10.1016/0040-4020(95)00234-y

  日期：1995.5

  studied in some disulfide containing peptides. In general, this reagent has proved to be effective in neat TFA at 0°C, with the obtention of the unprotected peptides in more than 99% yields and without reduction of the disulfide bridge bond. The use of Me2S as an additive resulted in faster reactions and disulfide scrambling was not observed. Whereas the Acm group proved to be stable to the reaction

  在某些含二硫键的肽中，已经研究了通过NH 4 I还原蛋氨酸亚砜的方法。通常，已证明该试剂可在0°C的纯TFA中有效，以超过99％的产率获得未保护的肽，并且不会还原二硫键。Me 2 S作为添加剂的使用导致反应更快，并且未观察到二硫化物加扰。事实证明，Acm基团对反应条件稳定，而未保护的含半胱氨酸的肽提供了相应的平行二聚体。