(S)-2-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-propionylamino}-3-(1H-indol-3-yl)-propionic acid methyl ester | 216588-42-0

• 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-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-propionylamino}-3-(1H-indol-3-yl)-propionic acid methyl ester
• CAS: 216588-42-0
• 化学式: C₃₁H₃₇N₅O₆
• 分子量: 575.665
• InChiKey: LVERIENIWXQBGG-ATANMQQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  42.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  154.41
• 氢给体数：
  5.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-2-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-propionylamino}-3-(1H-indol-3-yl)-propionic acid methyl ester 在 吡啶 、 乙酰氯 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 为溶剂， 反应 37.0h， 生成 methyl (6S,9S,12S)-12-acetamido-9-methyl-8,11-dioxo-6,7,8,9,10,11,12,13,18,19-decahydro-5H-[1,4]diazacyclotridecino[8,7-b:9,10-b']diindole-6-carboxylate
  参考文献：
  名称：

  Stabilization of a C 7 equatorial gamma turn in DMSO- d 6 by a ditryptophan crosslink

  摘要：

  Covalent crosslinks can control local peptide conformation. In tripeptide sequences of the general formula Cys-Xxx-Cys, cysteine disulfides have been previously shown to enforce a C-7 equatorial gamma-turn conformation (also referred to as an inverse gamma-turn). Much less is known about the effects of dityrosine and ditryptophan crosslinks on local peptide structure. In a series of tripeptides, ditryptophan crosslinks were formed using the two-step process of acid-promoted Mannich dimerization followed by oxidative aromatization. In these peptides, with the general formula Trp-Xxx-Trp (Xxx not equal Gly), ditryptophan crosslinks were found to stabilize a C-7 equatorial gamma-turn conformation in DMSO-d(6). Rigorous support for a C-7 equatorial conformation in the crosslinked sequence Trp-Pro-Trp came from a variety of H-1 NMR experiments and molecular modelling. Interproton distances were derived from NOE buildups that were determined through a series of double pulsed field gradient spin echo (DPFGSE) experiments. In addition, the small temperature dependence of the i + 2 NH chemical shifts (Delta delta/Delta T < 2 ppm/degrees C) provided further support for the intramolecular hydrogen bond which defines a gamma-turn. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00076-5
• 作为产物：
  描述：

  L-色氨酸甲酯 在 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (S)-2-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-propionylamino}-3-(1H-indol-3-yl)-propionic acid methyl ester
  参考文献：
  名称：

  Stabilization of a C 7 equatorial gamma turn in DMSO- d 6 by a ditryptophan crosslink

  摘要：

  Covalent crosslinks can control local peptide conformation. In tripeptide sequences of the general formula Cys-Xxx-Cys, cysteine disulfides have been previously shown to enforce a C-7 equatorial gamma-turn conformation (also referred to as an inverse gamma-turn). Much less is known about the effects of dityrosine and ditryptophan crosslinks on local peptide structure. In a series of tripeptides, ditryptophan crosslinks were formed using the two-step process of acid-promoted Mannich dimerization followed by oxidative aromatization. In these peptides, with the general formula Trp-Xxx-Trp (Xxx not equal Gly), ditryptophan crosslinks were found to stabilize a C-7 equatorial gamma-turn conformation in DMSO-d(6). Rigorous support for a C-7 equatorial conformation in the crosslinked sequence Trp-Pro-Trp came from a variety of H-1 NMR experiments and molecular modelling. Interproton distances were derived from NOE buildups that were determined through a series of double pulsed field gradient spin echo (DPFGSE) experiments. In addition, the small temperature dependence of the i + 2 NH chemical shifts (Delta delta/Delta T < 2 ppm/degrees C) provided further support for the intramolecular hydrogen bond which defines a gamma-turn. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00076-5