L-Asp-L-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: L-Asp-L-Phe-OMe
• 英文别名: 2,2,2-trifluoroethyl (3S)-4-[[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxo-3-(2,2,2-trifluoroethylamino)butanoate
• 化学式: C₁₈H₂₀F₆N₂O₅
• 分子量: 458.358
• InChiKey: ZWTSLFDSAHUEBA-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  阿斯巴甜 、 (1,1,1-trifluoroethyl) phenyl iodonium (N,N'-bis-trifluoromethylsulfonyl) imide 以80%的产率得到L-Asp-L-Phe-OMe
  参考文献：
  名称：

  A discovery tool at work: the unexpected properties of a two-carbon residue

  摘要：

  We report the very easy preparation of novel peptides 6a-n as represented by CF3CH2(L)Phe(L)UeOtBu (6a), a prospective antitumor compound. Peptides such as 6a are directly obtained via standard chemistry from a novel class of amino acids, N-alpha-trifluoroethyl amino acids 4. In fact, unexpectedly, the N-alpha-1,1,1-trifluoroethyl substitution completely deactivates the alpha -nitrogen. That is, compounds 4 behave exactly like N-alpha-protected amino acids, and take part in standard peptide synthesis accordingly. Representative compounds 4a-c are prepared by reaction of commercial amino acid t-butyl esters 2a-c with 1 eq iodonium salt 1 in dichloromethane/water at 22 degreesC in 1 h or less. The reaction is promoted by NaHCO3 (1.5 eq). The intermediate N-alpha-1,1,1-trifluoroethyl t-butyl esters 3a-c are hydrolyzed and separated from coproducts at the same time by treatment with aqueous HCl at 22 degreesC. Evaporation of the acid extracts provides analytically pure 4a-c in 78-98% yields. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(01)00377-3

文献信息

• A discovery tool at work: the unexpected properties of a two-carbon residue
  作者：Darryl D DesMarteau、Vittorio Montanari

  DOI：10.1016/s0022-1139(01)00377-3

  日期：2001.6

  We report the very easy preparation of novel peptides 6a-n as represented by CF3CH2(L)Phe(L)UeOtBu (6a), a prospective antitumor compound. Peptides such as 6a are directly obtained via standard chemistry from a novel class of amino acids, N-alpha-trifluoroethyl amino acids 4. In fact, unexpectedly, the N-alpha-1,1,1-trifluoroethyl substitution completely deactivates the alpha -nitrogen. That is, compounds 4 behave exactly like N-alpha-protected amino acids, and take part in standard peptide synthesis accordingly. Representative compounds 4a-c are prepared by reaction of commercial amino acid t-butyl esters 2a-c with 1 eq iodonium salt 1 in dichloromethane/water at 22 degreesC in 1 h or less. The reaction is promoted by NaHCO3 (1.5 eq). The intermediate N-alpha-1,1,1-trifluoroethyl t-butyl esters 3a-c are hydrolyzed and separated from coproducts at the same time by treatment with aqueous HCl at 22 degreesC. Evaporation of the acid extracts provides analytically pure 4a-c in 78-98% yields. (C) 2001 Elsevier Science B.V. All rights reserved.