Fmoc-Gly-Phe-Leu-OH | 103144-79-2

• 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: Fmoc-Gly-Phe-Leu-OH
• 英文别名: (2S)-2-[[(2S)-2-[[2-(9H-fluoren-9-ylmethoxycarbonylamino)acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoic acid
• CAS: 103144-79-2
• 化学式: C₃₂H₃₅N₃O₆
• 分子量: 557.646
• InChiKey: APNPQLJKSDXCBZ-NSOVKSMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Fmoc-Gly-Phe-Leu-OH 在 1-羟基苯并三唑 、 二乙醇胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 glycyl-L-phenylalanyl-L-leucyl-glycyl-2-(5-fluorouracil-1-yl)glycine ethyl ester
  参考文献：
  名称：

  Synthesis of peptide derivatives of 5-fluorouracil

  摘要：

  The preparation of di-, tetra- and pentapeptides carrying 5-fluorouracil as an a-substituent of a terminal glycine moiety is described. The dipeptide compounds were synthetized by addition of ethyl glyoxylate to N-(benzyl-oxycarbonyl)-amino acid amides, subsequent acetylation of resulting hydroxyl groups,displacement of acetate groups by 5-fluorouracil, and removal of protective group. Tetra- and pentapeptides were prepared from these dipeptides by coupling methods commonly used in peptide chemistry.

  DOI：

  10.1016/s0040-4020(01)90395-3
• 作为产物：
  描述：

  (S)-2-{(Z)-2-[2-(9H-Fluoren-9-ylmethoxycarbonylamino)-acetylamino]-3-phenyl-acryloylamino}-4-methyl-pentanoic acid 在 chiral BF4 氢气 、 三氟乙酸 作用下， 以 异丙醇 、 甲苯 为溶剂， 反应 72.0h， 生成 Fmoc-Gly-Phe-Leu-OH
  参考文献：
  名称：

  聚合物载体上肽的催化不对称合成

  摘要：

  描述了一种新颖的方法，通过使用与手性二膦配体的铑配合物作为催化剂，通过与Wang树脂连接的脱氢三肽的催化不对称氢化来合成肽。

  DOI：

  10.1016/s0040-4039(00)78184-6

文献信息

• THAL, a Sterically Unhindered Linker for the Solid-Phase Synthesis of Acid-Sensitive Protected Peptide Acids
  作者：Albert Isidro-Llobet、Ulrik Boas、Knud J. Jensen、Mercedes Álvarez、Fernando Albericio

  DOI：10.1021/jo800535m

  日期：2008.9.19

  Acid Labile) is described as a new linker for the solid-phase synthesis of peptide carboxylic acids. It is based on the electron-rich 3,4-ethylenedioxythenyl (EDOTn) moiety and allows the obtention of free and tert-butyl-protected peptides by cleavage with 90% and 0.5% TFA, respectively. This very high acid lability makes it useful for the synthesis of sensitive peptides. Free and tert-butyl-protected

  5-（4-羟苯基）-3,4-亚乙二氧基噻吩醇（THAL，噻吩酸不稳定）被描述为肽羧酸固相合成的新连接体。它基于富含电子的3,4-亚乙二氧基乙烯基（EDOTn）部分，并可以通过分别用90％和0.5％TFA裂解获得游离的和叔丁基保护的肽。这种极高的酸不稳定性使其可用于合成敏感肽。游离和叔丁基保护的亮脑啡肽已合成为模型，以证明接头的效用。
• Synthesis of peptide derivatives of 5-fluorouracil
  作者：Marieta Nichifor、Etienne H. Schacht

  DOI：10.1016/s0040-4020(01)90395-3

  日期：1994.3

  The preparation of di-, tetra- and pentapeptides carrying 5-fluorouracil as an a-substituent of a terminal glycine moiety is described. The dipeptide compounds were synthetized by addition of ethyl glyoxylate to N-(benzyl-oxycarbonyl)-amino acid amides, subsequent acetylation of resulting hydroxyl groups,displacement of acetate groups by 5-fluorouracil, and removal of protective group. Tetra- and pentapeptides were prepared from these dipeptides by coupling methods commonly used in peptide chemistry.
• Catalytic asymmetric synthesis of peptides on polymer support
  作者：Iwao Ojima、Chung-Ying Tsai、Zhaoda Zhang

  DOI：10.1016/s0040-4039(00)78184-6

  日期：1994.8

  A novel approach to the synthesis of peptides through the catalytic asymmetric hydrogenation of dehydrotripeptides linked to the Wang resin, using rhodium complexes with chiral diphosphine ligands as the catalysts, is described.

  描述了一种新颖的方法，通过使用与手性二膦配体的铑配合物作为催化剂，通过与Wang树脂连接的脱氢三肽的催化不对称氢化来合成肽。