N-benzoyl-L-alanyl-[α,α-dimethyl-(R)-β-homoleucyl]-L-phenylalanine methyl ester | 1387020-56-5

• 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: N-benzoyl-L-alanyl-[α,α-dimethyl-(R)-β-homoleucyl]-L-phenylalanine methyl ester
• 英文别名: methyl (2S)-2-[[(3R)-3-[[(2S)-2-benzamidopropanoyl]amino]-2,2,5-trimethylhexanoyl]amino]-3-phenylpropanoate
• CAS: 1387020-56-5
• 化学式: C₂₉H₃₉N₃O₅
• 分子量: 509.646
• InChiKey: ITWZZBJVKFVJJU-NKKJXINNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  、 L-苯丙氨酸甲酯盐酸盐 在 1-羟基苯并三唑 、 1,2-二氯乙烷 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以51%的产率得到N-benzoyl-L-alanyl-[α,α-dimethyl-(S)-β-homoleucyl]-L-phenylalanine methyl ester
  参考文献：
  名称：

  Conformation and Chiral Effects in α,β,α-Tripeptides

  摘要：

  Short alpha,beta,alpha-tripeptides comprising a central chiral trisubstituted beta(2,2,3)*-amino acid residue form unusual gamma-turns and delta-turns in CDCl3 and DMSO-d(6) solutions but do not form beta-turns. Thermal coefficients of backbone amide protons, 2D-NMR spectra, and molecular modeling revealed that these motifs were strongly dependent on the configuration (chiral effect) of the central beta-amino acid residue within the triad. Accordingly, SSS tripeptides adopted an intraresidual gamma-turn like (C6) arrangement in the central beta-amino acid, whereas SRS diastereomers preferred an extended delta-turn (C9) conformation. A different SRS-stabilizing bias was observed in the crystal structures of the same compounds, which shared the extended delta-turn (C9) found in solution, but incorporated an additional extended beta-turn (C11) to form an overlapped double turn motif.

  DOI：

  10.1021/jo300892u