S-[2-(butylamino)ethyl] (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 | 1433900-08-3

• 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-[2-(butylamino)ethyl] (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: 1433900-08-3
• 化学式: C₃₂H₆₂N₁₀O₇S
• 分子量: 730.973
• InChiKey: AYWRMOMABPASRU-WOXHBLBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  50
• 可旋转键数：
  27
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  311
• 氢给体数：
  10
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  Fmoc-L-异亮氨酸 、 Fmoc-Pbf-L-精氨酸 、 2-n-丁氨基乙硫醇 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (2S,3S)-2-[[2-[[2-[[(2S,3S)-2-[[(2S,3R)-2-amino-3-hydroxybutanoyl]amino]-3-methylpentanoyl]amino]acetyl]amino]acetyl]amino]-N-[(2S)-1-[butyl(2-sulfanylethyl)amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]-3-methylpentanamide 、 S-[2-(butylamino)ethyl] (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：

  A Thioethylalkylamido (TEA) Thioester Surrogate in the Synthesis of a Cyclic Peptide via a Tandem Acyl Shift

  摘要：

  The cyclic cystine-knot peptide, kalata B1, was synthesized by employing a novel Fmoc-compatible thioethylalkylamido (TEA) thioester surrogate via an N-S acyl shift followed by a thiol-thioester exchange reaction. TEA thioester surrogate is cost-effective, conveniently prepared in one-step with starting materials, readily available from commercial sources, and highly efficient in preparing peptide thioesters.

  DOI：

  10.1021/ol400801k

文献信息

• A Thioethylalkylamido (TEA) Thioester Surrogate in the Synthesis of a Cyclic Peptide via a Tandem Acyl Shift
  作者：Misako Taichi、Xinya Hemu、Yibo Qiu、James P. Tam

  DOI：10.1021/ol400801k

  日期：2013.6.7

  The cyclic cystine-knot peptide, kalata B1, was synthesized by employing a novel Fmoc-compatible thioethylalkylamido (TEA) thioester surrogate via an N-S acyl shift followed by a thiol-thioester exchange reaction. TEA thioester surrogate is cost-effective, conveniently prepared in one-step with starting materials, readily available from commercial sources, and highly efficient in preparing peptide thioesters.