N-phenylalanine methyl ester | 145641-42-5

• 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-phenylalanine methyl ester
• 英文别名: methyl (2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropyl]sulfinylamino]-3-phenylpropanoate
• CAS: 145641-42-5；145682-41-3
• 化学式: C₂₄H₃₂N₂O₅S
• 分子量: 460.594
• InChiKey: UDRQEVDPRSIBBF-FITADUECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-phenylalanine methyl ester 在 ruthenium trichloride 、 sodium periodate 作用下， 以79%的产率得到N-phenylalanine methyl ester
  参考文献：
  名称：

  Synthesis of peptides containing the β-substituted aminoethane sulfinamide or sulfonamide transition-state isostere derived from amino acids

  摘要：

  Alpha-amino acids can be converted to homochiral beta-substituted aminoethane sulfinamide or sulfonamide transition-state isosteres, which can be incorporated into peptides. These transition-state analogues e.g. the sulfonamide isostere of Phe-Phe will be used for the generation of catalytic antibodies as well as for the development of protease inhibitors.

  DOI：

  10.1016/s0040-4039(00)60981-4
• 作为产物：
  描述：

  ethoxycarbonyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoate 在 N-甲基吗啉 、 sodium tetrahydroborate 、 乙酸酐 、 氯 、 caesium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N-phenylalanine methyl ester
  参考文献：
  名称：

  Synthesis of Peptidosulfinamides and Peptidosulfonamides: Peptidomimetics Containing the Sulfinamide or Sulfonamide Transition-State Isostere

  摘要：

  Synthetic routes are described toward the preparation of alpha- as well as beta-substituted aminoethanesulfinyl chlorides, starting from either an aldehyde or from an amino acid derivative. The sulfinyl chlorides are used as building blocks for the preparation of homochiral alpha- or beta- substituted sulfinamide and sulfonamide transition-state isosteres. The methodology has been applied to the synthesis of peptidosulfonamide peptidomimetics such as a hapten needed for the generation of antibodies and potential HIV protease inhibitors. In addition, the beta-substituted aminoethanesulfinyl chlorides were used as building blocks for the preparation of a tetrapeptidosulfonamide, which can be considered as a biopolymer mimetic, employing a repetition of a cycle of three reactions: coupling of the sulfinyl chloride to the N-terminus of the growing peptidosulfonamide, oxidation to the sulfonamide, and deprotection of the N-terminus.

  DOI：

  10.1021/jo00121a038

文献信息

• Synthesis of peptides containing the β-substituted aminoethane sulfinamide or sulfonamide transition-state isostere derived from amino acids
  作者：Wilna J. Moree、Gijs A. van der Marel、Rob M.J. Liskamp

  DOI：10.1016/s0040-4039(00)60981-4

  日期：1992.10

  Alpha-amino acids can be converted to homochiral beta-substituted aminoethane sulfinamide or sulfonamide transition-state isosteres, which can be incorporated into peptides. These transition-state analogues e.g. the sulfonamide isostere of Phe-Phe will be used for the generation of catalytic antibodies as well as for the development of protease inhibitors.
• Synthesis of Peptidosulfinamides and Peptidosulfonamides: Peptidomimetics Containing the Sulfinamide or Sulfonamide Transition-State Isostere
  作者：Wilna J. Moree、Gijs A. van der Marel、Rob J. Liskamp

  DOI：10.1021/jo00121a038

  日期：1995.8

  Synthetic routes are described toward the preparation of alpha- as well as beta-substituted aminoethanesulfinyl chlorides, starting from either an aldehyde or from an amino acid derivative. The sulfinyl chlorides are used as building blocks for the preparation of homochiral alpha- or beta- substituted sulfinamide and sulfonamide transition-state isosteres. The methodology has been applied to the synthesis of peptidosulfonamide peptidomimetics such as a hapten needed for the generation of antibodies and potential HIV protease inhibitors. In addition, the beta-substituted aminoethanesulfinyl chlorides were used as building blocks for the preparation of a tetrapeptidosulfonamide, which can be considered as a biopolymer mimetic, employing a repetition of a cycle of three reactions: coupling of the sulfinyl chloride to the N-terminus of the growing peptidosulfonamide, oxidation to the sulfonamide, and deprotection of the N-terminus.