N1-trityl-3α-hydroxypyrrolo[2,3-b]indolylglycine methyl ester

• 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: N1-trityl-3α-hydroxypyrrolo[2,3-b]indolylglycine methyl ester
• 英文别名: methyl 2-[[(2S,3aR,8bS)-8b-hydroxy-3-trityl-1,2,3a,4-tetrahydropyrrolo[2,3-b]indole-2-carbonyl]amino]acetate
• 化学式: C₃₃H₃₁N₃O₄
• 分子量: 533.627
• InChiKey: LAMQDSCYIWBJJS-YXQUNVLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  90.9
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl 2-[(2S)-3-(1H-indol-3-yl)-2-[(triphenylmethyl)amino]propanamido]acetate 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 0.25h， 以35%的产率得到N1-trityl-3α-hydroxypyrrolo[2,3-b]indolylglycine methyl ester
  参考文献：
  名称：

  High Yielding Synthesis of 3a-Hydroxypyrrolo[2,3-b]indoline Dipeptide Methyl Esters:  Synthons for Expedient Introduction of the Hydroxypyrroloindoline Moiety into Larger Peptide-Based Natural Products and for the Creation of Tryptathionine Bridges

  摘要：

  This work describes a rapid and high yielding oxidation of 14 tryptophanylated amino acid methyl esters to the corresponding 3 alpha-hydroxypyrrolo[2,3-b]indoline (Hpi) amino acids with generally facile separation of syn-cis and anti-cis diastereomers. Structural X-ray diffraction data are presented for both diastereomers of Tr-Hpi-Gly-OMe, which allow for a putative assignment of the other 13 pairs of diastereomers reported herein, based on correlations with H-1 NMR chemical shifts. Selective and high yielding deprotection at either the N or C terminus is described, allowing the Hpi motif to be introduced efficiently into potential targets with minimal protecting group manipulation. Two tripeptides containing Hpi and cysteine were prepared and treated with acid in the Savige-Fontana reaction to produce a cyclic tryptathionine linkage, characteristic of both amatoxins and phallotoxins.

  DOI：

  10.1021/jo051105t

文献信息

• High Yielding Synthesis of 3<i>a</i>-Hydroxypyrrolo[2,3-<i>b</i>]indoline Dipeptide Methyl Esters:  Synthons for Expedient Introduction of the Hydroxypyrroloindoline Moiety into Larger Peptide-Based Natural Products and for the Creation of Tryptathionine Bridges
  作者：Jonathan P. May、Pierre Fournier、Jonathan Pellicelli、Brian O. Patrick、David M. Perrin

  DOI：10.1021/jo051105t

  日期：2005.10.1

  This work describes a rapid and high yielding oxidation of 14 tryptophanylated amino acid methyl esters to the corresponding 3 alpha-hydroxypyrrolo[2,3-b]indoline (Hpi) amino acids with generally facile separation of syn-cis and anti-cis diastereomers. Structural X-ray diffraction data are presented for both diastereomers of Tr-Hpi-Gly-OMe, which allow for a putative assignment of the other 13 pairs of diastereomers reported herein, based on correlations with H-1 NMR chemical shifts. Selective and high yielding deprotection at either the N or C terminus is described, allowing the Hpi motif to be introduced efficiently into potential targets with minimal protecting group manipulation. Two tripeptides containing Hpi and cysteine were prepared and treated with acid in the Savige-Fontana reaction to produce a cyclic tryptathionine linkage, characteristic of both amatoxins and phallotoxins.