H-L-Asp-L-(αMe)Phe-OMe

• 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: H-L-Asp-L-(αMe)Phe-OMe
• 英文别名: (3S)-3-amino-4-[[(2S)-1-methoxy-2-methyl-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic acid
• 化学式: C₁₅H₂₀N₂O₅
• 分子量: 308.334
• InChiKey: YINNYHLJBWDWDV-NHYWBVRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  异氰酸对硝基苯 、 H-L-Asp-L-(αMe)Phe-OMe 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以72%的产率得到para-nitrophenylcarbamoyl-L-aspartyl-L-(α-methyl)phenylalanine methyl ester
  参考文献：
  名称：

  Bioactive and model peptides characterized by the helicogenic (αMe)Phe residue

  摘要：

  We have synthesized and fully characterized the hypersweet super-aspartame analogue pCN-C6H4-NHCO-L-Asp-L-(alphaMe)Phe-OMe 1; the [D-(alphaMe)Phe]3-analogue of the formyl-methionyl tripeptide chemoattractant HCO-L-Met-L-Leu-D-(alphaMe)Phe-OMe 2, the first D-chemotactic peptide being found more active than its L-diastereomer; and the model pentapeptide pBrBz-D-(alphaMe)Phe-(Aib)2-D-(alphaMe)Phe-Aib-OtBu 3. The preferred conformation of the three peptides, as determined by X-ray diffraction analyses, is discussed in terms of the proposed receptor models for sweet perception [peptide 1] and neutrophil chemotaxis [peptide 4, and as a promising candidate for molecular recognition studies [peptide 3].

  DOI：

  10.1016/s0040-4020(01)90220-0

文献信息

• N-ALKYLASPARTYLDIPEPTIDE ESTER DERIVATIVES AND SWEETENERS
  申请人：Ajinomoto Co., Inc.

  公开号：EP1114828B1

  公开（公告）日：2008-03-12
• Bioactive and model peptides characterized by the helicogenic (αMe)Phe residue
  作者：Claudio Toniolo、Fernando Formaggio、Marco Crisma、Giovanni Valle、Wilhelmus H.J. Boesten、Hans E. Schoemaker、Johan Kamphuis、Piero A. Temussi、Elmer L. Becker、Gilles Précigoux

  DOI：10.1016/s0040-4020(01)90220-0

  日期：1993.3

  We have synthesized and fully characterized the hypersweet super-aspartame analogue pCN-C6H4-NHCO-L-Asp-L-(alphaMe)Phe-OMe 1; the [D-(alphaMe)Phe]3-analogue of the formyl-methionyl tripeptide chemoattractant HCO-L-Met-L-Leu-D-(alphaMe)Phe-OMe 2, the first D-chemotactic peptide being found more active than its L-diastereomer; and the model pentapeptide pBrBz-D-(alphaMe)Phe-(Aib)2-D-(alphaMe)Phe-Aib-OtBu 3. The preferred conformation of the three peptides, as determined by X-ray diffraction analyses, is discussed in terms of the proposed receptor models for sweet perception [peptide 1] and neutrophil chemotaxis [peptide 4, and as a promising candidate for molecular recognition studies [peptide 3].