Fmoc-Gly-Phe-OEt | 139449-00-6

• 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-OEt
• 英文别名: ethyl (((9H-fluoren-9-yl)methoxy)carbonyl)glycyl-L-phenylalaninate；Fmoc-GF-OEt；ethyl (2S)-2-[[2-(9H-fluoren-9-ylmethoxycarbonylamino)acetyl]amino]-3-phenylpropanoate
• CAS: 139449-00-6
• 化学式: C₂₈H₂₈N₂O₅
• 分子量: 472.541
• InChiKey: XAUGWOBTNXFFNX-VWLOTQADSA-N

物化性质

• 沸点：
  700.1±60.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  93.73
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (2S)-2-氨基-3-苯丙酸乙酯 、 Fmoc-Gly-SH 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以27%的产率得到Fmoc-Gly-Phe-OEt
  参考文献：
  名称：

  Promising General Solution to the Problem of Ligating Peptides and Glycopeptides

  摘要：

  Our global goal is that of synthesizing complex polypeptides and glycopeptides in homogeneous form. Chemistry-derived access to homogeneous biologics could well have useful consequences in the discovery of drugs and vaccines. The key finding in this study is that thio acids can become highly competent acyl donors following even trace levels of oxidative activation, thereby undergoing amide bond formation upon reaction with N-terminal peptides. Though our data set does not establish the specific mechanism of this reaction, a framework to account for the fact that minute levels of oxidation actuate amide bond formation with high turnover is offered. An apparently general coupling of thio acids (including complex peptide thio acids with N-termini of complex peptides) has thus been realized. These ligations are conducted with minimal alpha-epimerization in the C-terminal group and allow for the coupling of N-terminal and C-terminal glycopeptides en route to homogeneous glycoproteins.

  DOI：

  10.1021/ja1084628

文献信息

• TiF₄-catalyzed direct amidation of carboxylic acids and amino acids with amines
  作者：Abdulkhaliq A. Alawaed、P. Veeraraghavan Ramachandran

  DOI：10.1039/d3ob01943h

  日期：——

  Unlike other metal fluorides, catalytic titanium tetrafluoride enhances the direct amidation of aromatic and aliphatic carboxylic acids and N-protected amino acids in refluxing toluene. While aromatic acids were converted to amides with 10 mol% of the catalyst within 24 h, aliphatic acids underwent a faster reaction (12 h), with lower catalyst loading (5 mol%). This protocol is equally efficient with

  与其他金属氟化物不同，催化四氟化钛增强了芳香族和脂肪族羧酸以及N-保护的氨基酸在回流甲苯中的直接酰胺化。虽然芳香酸在 10 mol% 的催化剂下在 24 小时内转化为酰胺，但脂肪酸的反应速度更快（12 小时），且催化剂负载量较低（5 mol%）。该方案对于烷基胺和芳基胺同样有效，可提供多种甲酰胺和肽，产率达 60-99%。
• Formation of peptide thioamides by use of Fmoc amino monothioacids and PyBOP.
  作者：Thomas Høeg-Jensen、Mogens Havsteen Jakobsen、Carl Erik Olsen、Arne Holm

  DOI：10.1016/0040-4039(91)80549-l

  日期：1991.12

  Endothiopeptides have been obtained by using PyBOP(R) promoted coupling between Fmoc-protected amino monothioacids and amino acid or peptide esters. The protected endothiopeptides (Fmoc-Gly-psi(CSNH)-Phe-OEt, Fmoc-Tyr(Bu(t))-psi(CSNH)-Gly-Gly-Phe-Leu-OBu(t) and (Fmoc-Gln(Trt)-psi(CSNH)-Phe-OEt) were formed (55, 45 and 37% yield) in admixture with the corresponding oxopeptides, from which they were easily separated chromatographically. Preliminary racemisation studies indicate that products of high optical purity are obtained. The mechanism for endothiopeptide formation is briefly discussed.