S-(4-methylphenyl) (2S)-2-[[(2S,3S)-2-[[2-[[2-[[(2S,3S)-2-[[(2S,3R)-2-amino-3-hydroxybutanoyl]amino]-3-methylpentanoyl]amino]acetyl]amino]acetyl]amino]-3-methylpentanoyl]amino]-5-(diaminomethylideneamino)pentanethioate | 1300037-71-1

• 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: S-(4-methylphenyl) (2S)-2-[[(2S,3S)-2-[[2-[[2-[[(2S,3S)-2-[[(2S,3R)-2-amino-3-hydroxybutanoyl]amino]-3-methylpentanoyl]amino]acetyl]amino]acetyl]amino]-3-methylpentanoyl]amino]-5-(diaminomethylideneamino)pentanethioate
• CAS: 1300037-71-1
• 化学式: C₃₃H₅₅N₉O₇S
• 分子量: 721.922
• InChiKey: HDCRQTUTWRIEOF-BCLMZUBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  50
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  299
• 氢给体数：
  9
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]ethyl-[12-[2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]ethyl-(2-hydroxyethyl)-methylazaniumyl]dodecyl]-(2-hydroxyethyl)-methylazanium 、 4-甲苯硫酚 在 三氟甲磺酸 、 三氟乙酸 作用下， 反应 2.0h， 生成 、 S-(4-methylphenyl) (2S)-2-[[(2S,3S)-2-[[2-[[2-[[(2S,3S)-2-[[(2S,3R)-2-amino-3-hydroxybutanoyl]amino]-3-methylpentanoyl]amino]acetyl]amino]acetyl]amino]-3-methylpentanoyl]amino]-5-(diaminomethylideneamino)pentanethioate 、 、
  参考文献：
  名称：

  Acid-Catalyzed Tandem Thiol Switch for Preparing Peptide Thioesters from Mercaptoethyl Esters

  摘要：

  An efficient method compatible with Fmoc synthesis for preparing peptide thioesters via an acid-catalyzed tandem "thiol switch" of esters Is described first by an intramolecular O-S acyl shift and then by an intermolecular S S exchange, with concurrent deblocking of side chain protection groups.

  DOI：

  10.1021/ol2007204

文献信息

• Tandem Thiol Switch Synthesis of Peptide Thioesters via N–S Acyl Shift on Thiazolidine
  作者：Rohit K. Sharma、James P. Tam

  DOI：10.1021/ol202047q

  日期：2011.10.7

  An efficient "thiol switch" approach for the synthesis of peptide thioesters via an acid-catalyzed N-S acyl shift and a thioester exchange reaction in tandem with concurrent removal of protecting groups is described. This method employs novel 2-(thiomethyl)thiazolidine (TMT)-anchored resins and is fully compatible with Fmoc chemistry.