Boc-Phe-Leu(γ-OH)-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: Boc-Phe-Leu(γ-OH)-Phe-OMe
• 英文别名: methyl (2S)-2-[[(2S)-4-hydroxy-4-methyl-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]pentanoyl]amino]-3-phenylpropanoate
• 化学式: C₃₀H₄₁N₃O₇
• 分子量: 555.671
• InChiKey: BQMBTSRRVJQNJU-HJOGWXRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  40
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  Boc-Phe-Leu-Phe-OMe 在 二甲基二环氧乙烷 作用下， 以 丙酮 为溶剂， 反应 72.0h， 以96.3%的产率得到Boc-Phe-Leu(γ-OH)-Phe-OMe
  参考文献：
  名称：

  A New and Efficient Synthesis of Unnatural Amino Acids and Peptides by Selective 3,3-Dimethyldioxirane Side-Chain Oxidation

  摘要：

  N-Boc derivatives of Leu, Met, Thr, Trp, and Pro, the properties of which resemble those of the respective alpha-amino acid residues present in proteins, rapidly oxidize in the presence of 3,3-dimethyldioxirane to give different products depending on the structure of the oxidizable group in the side chain. A high regioselectivity for the oxygen atom insertion into the gamma-CH bond of Leu residues with respect to the weaker alpha-CH bond was observed. A position selectivity in the oxidation of peptides containing more than one Leu residue was also found.

  DOI：

  10.1021/jo990185w

文献信息

• A New and Efficient Synthesis of Unnatural Amino Acids and Peptides by Selective 3,3-Dimethyldioxirane Side-Chain Oxidation
  作者：Raffaele Saladino、Maurizio Mezzetti、Enrico Mincione、Ines Torrini、Mario Paglialunga Paradisi、Gaia Mastropietro

  DOI：10.1021/jo990185w

  日期：1999.11.1

  N-Boc derivatives of Leu, Met, Thr, Trp, and Pro, the properties of which resemble those of the respective alpha-amino acid residues present in proteins, rapidly oxidize in the presence of 3,3-dimethyldioxirane to give different products depending on the structure of the oxidizable group in the side chain. A high regioselectivity for the oxygen atom insertion into the gamma-CH bond of Leu residues with respect to the weaker alpha-CH bond was observed. A position selectivity in the oxidation of peptides containing more than one Leu residue was also found.