Boc-(D)Trp-(D)Trp | 160623-01-8

• 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: Boc-(D)Trp-(D)Trp
• 英文别名: N-(tert-Butoxycarbonyl)-D-tryptophyl-D-tryptophan；(2R)-3-(1H-indol-3-yl)-2-[[(2R)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoic acid
• CAS: 160623-01-8
• 化学式: C₂₇H₃₀N₄O₅
• 分子量: 490.559
• InChiKey: ZPYPARPDPMPFPW-DHIUTWEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  136
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  D-色氨酸甲酯 在 sodium hydroxide 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 Boc-(D)Trp-(D)Trp
  参考文献：
  名称：

  Second Harmonic Optical Activity of Tryptophan Derivatives Adsorbed at the Air/Water Interface

  摘要：

  Optical activity in second harmonic reflection from the air/water interface of solutions of simple tryptophan (trp) derivatives has been investigated. The derivatives include D- and L-optical isomers of Boc-trp and DD-and LL-isomers of the dipeptide Boc-trp-trp, where Boc is tert-butyloxycarbonyl. An experimental method based on polarization modulation of fundamental radiation by rotation of a quarter-wave retardation plate has been used to completely characterize the second-order nonlinear susceptibilities of the chiral surfaces, for the fundamental wavelength lambda = 564 nm. Boc-trp and Boc-trp-trp show similar chiral contributions to the nonlinear susceptibilities, which indicates that the chiral response does not depend on intramolecular interactions between trp residues. The efficiency of second harmonic reflection has been shown to be resonantly enhanced at the two-photon level, in the region of the near-UV bands (similar to280 nm) of the indole chromophore of tryptophan. The origin of the chiral response is discussed in terms of simple microscopic models, and a comparison is made with optical activity of tryptophanyl compounds in linear spectroscopy. The peptide gramicidin, incorporating several trp residues, showed no evidence of optical activity in second harmonic reflection from the air/water interface. This indicates that second harmonic optical activity is sensitive to structural effects such as conformational and orientational distributions of trp residues at the interface.

  DOI：

  10.1021/jp036252e