(S)-2-Amino-N-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(1H-indol-3-yl)-propionamide | 442900-70-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-2-Amino-N-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(1H-indol-3-yl)-propionamide
• CAS: 442900-70-1
• 化学式: C₂₉H₃₅N₃O₂Si
• 分子量: 485.701
• InChiKey: SSUBSURZKSFIGS-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  80.14
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-2-Amino-N-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(1H-indol-3-yl)-propionamide 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， -10.0~30.0 ℃ 、100.0 kPa 条件下， 反应 15.0h， 生成
  参考文献：
  名称：

  Solution phase synthesis and purification of the minigramicidin ion channels and a succinyl-linked gramicidin

  摘要：

  Peptides with alternating D- and L-configured residues as found in the natural ion channel active peptide gramicidin A (gA) are important building blocks for artificially engineered ion channels. We detail an optimised solution phase synthesis employing a convergent assembly of peptide building blocks, giving access to the minigramicidines and a succinyl linked gA derivative on preparative scale. Moreover, the minigramicidines were investigated for secondary structure formation by CD-spectroscopy. which was discovered to be medium and capping-group dependent. A parallel, left-handed double-beta-helix seems to be generally favoured in organic solvents for the minigramicidines. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00179-5
• 作为产物：
  描述：

  2-((tert-butyldiphenylsilyl)oxy)ethanamine 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 5.0h， 生成 (S)-2-Amino-N-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(1H-indol-3-yl)-propionamide
  参考文献：
  名称：

  Solution phase synthesis and purification of the minigramicidin ion channels and a succinyl-linked gramicidin

  摘要：

  Peptides with alternating D- and L-configured residues as found in the natural ion channel active peptide gramicidin A (gA) are important building blocks for artificially engineered ion channels. We detail an optimised solution phase synthesis employing a convergent assembly of peptide building blocks, giving access to the minigramicidines and a succinyl linked gA derivative on preparative scale. Moreover, the minigramicidines were investigated for secondary structure formation by CD-spectroscopy. which was discovered to be medium and capping-group dependent. A parallel, left-handed double-beta-helix seems to be generally favoured in organic solvents for the minigramicidines. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00179-5

文献信息

• Tetrahydropyran-Amino Acids: Novel Building Blocks for Gramicidin-Hybrid Ion Channels
  作者：Sabine Schröder、Anna K. Schrey、Andrea Knoll、Philipp Reiß、Burkhard Ziemer、Ulrich Koert

  DOI：10.1002/ejoc.200600068

  日期：2006.6

  a δ-amino acid has been achieved starting from N-Boc-leucinal. The THP amino acid was incorporated into peptide sequences and the structural consequences were studied by X-ray crystallography and NMR analysis. Single-channel current measurements showed that the THP amino acid is a suitable substitute for positions 11 and 12 of the gramicidin ion channel. The resulting hybrid ion channel revealed Eisenman

  从 N-Boc-亮氨酸开始，已经实现了带有 δ-氨基酸的顺式-2,6-二取代四氢吡喃的立体选择性合成。THP 氨基酸被纳入肽序列，并通过 X 射线晶体学和 NMR 分析研究结构结果。单通道电流测量表明，THP 氨基酸是短杆菌肽离子通道 11 和 12 位的合适替代品。由此产生的混合离子通道显示了 Eisenman I 离子选择性和通道停留时间的离子依赖性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)