Fmoc-Phe-Val-OMe | 827018-98-4

• 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-Phe-Val-OMe
• 英文别名: methyl (2S)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropanoyl]amino]-3-methylbutanoate
• CAS: 827018-98-4
• 化学式: C₃₀H₃₂N₂O₅
• 分子量: 500.594
• InChiKey: JJFTVOSXDZJZKC-SVBPBHIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Fmoc-Phe-Val-OMe 在 三氯化铝 、 N,N-二甲基苯胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 H-Phe-Val-OMe
  参考文献：
  名称：

  在 AlCl3/N,N-二甲基苯胺试剂系统中通过调节摩尔比对 N-Fmoc-氨基酸和 N-Fmoc-二肽甲酯的 α-氨基和羧基官能团进行选择性和化学选择性脱保护

  摘要：

  N-Fmoc-α-氨基酸和 N-Fmoc-肽甲酯中的氨基和羧基官能团可以通过使用试剂系统 AlCl3/N,N-二甲基苯胺 (DMA) 进行选择性化学选择性脱保护。该过程的化学选择性是通过调节路易斯酸和 DMA 的相对摩尔比来控制的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  DOI：

  10.1002/ejoc.200400321
• 作为产物：
  描述：

  N-Phthaloyl-L-Phe-Val-OH 在 氯化亚砜 、 碳酸氢钠 、 乙二胺 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 28.0h， 生成 Fmoc-Phe-Val-OMe
  参考文献：
  名称：

  Site-Selective C(sp³)–H Functionalization of Di-, Tri-, and Tetrapeptides at the N-Terminus

  摘要：

  Although the syntheses of novel and diverse peptides rely mainly on traditional coupling using unnatural amino acids, postsynthetic modification of peptides could provide a complementary method for the preparation of nonproteinogenic peptides. Site selectivity of postsynthetic modification of peptides is usually achieved by targeting reactive moieties, such as the thiol group of cysteine or the C-2 position of tryptophan. Herein, we report the development of site-selective functionalizations of inert C(sp(3))-H bonds of N-terminal amino acids in di-, tri-, and tetrapeptides without installing a directing group. The native amino acid moiety within the peptide is used as a ligand to accelerate the C-H activation reaction. In the long run, this newly uncovered reactivity could provide guidance for developing site-selective C(sp(3))-H activation toward postsynthetic modification of a broader range of peptides.

  DOI：

  10.1021/ja510233h

文献信息

• Site-Selective C(sp³)–H Functionalization of Di-, Tri-, and Tetrapeptides at the N-Terminus
  作者：Wei Gong、Guofu Zhang、Tao Liu、Ramesh Giri、Jin-Quan Yu

  DOI：10.1021/ja510233h

  日期：2014.12.3

  Although the syntheses of novel and diverse peptides rely mainly on traditional coupling using unnatural amino acids, postsynthetic modification of peptides could provide a complementary method for the preparation of nonproteinogenic peptides. Site selectivity of postsynthetic modification of peptides is usually achieved by targeting reactive moieties, such as the thiol group of cysteine or the C-2 position of tryptophan. Herein, we report the development of site-selective functionalizations of inert C(sp(3))-H bonds of N-terminal amino acids in di-, tri-, and tetrapeptides without installing a directing group. The native amino acid moiety within the peptide is used as a ligand to accelerate the C-H activation reaction. In the long run, this newly uncovered reactivity could provide guidance for developing site-selective C(sp(3))-H activation toward postsynthetic modification of a broader range of peptides.
• Alternative and Chemoselective Deprotection of the ?-Amino and Carboxy Functions ofN-Fmoc-Amino Acid andN-Fmoc-Dipeptide Methyl Esters by Modulation of the Molar Ratio in the AlCl3/N,N-Dimethylaniline Reagent System
  作者：Maria�Luisa Di Gioia、Antonella Leggio、Adolfo Le Pera、Angelo Liguori、Francesca Perri、Carlo Siciliano

  DOI：10.1002/ejoc.200400321

  日期：2004.11

  The amino and carboxy functions in N-Fmoc-α-amino acid and N-Fmoc-peptide methyl esters can be alternatively and chemoselectively deprotected by treatment with the reagent system AlCl3/N,N-dimethylaniline (DMA). The chemoselectivity of the process is controlled by modulating the relative molar ratio of the Lewis acid and DMA. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  N-Fmoc-α-氨基酸和 N-Fmoc-肽甲酯中的氨基和羧基官能团可以通过使用试剂系统 AlCl3/N,N-二甲基苯胺 (DMA) 进行选择性化学选择性脱保护。该过程的化学选择性是通过调节路易斯酸和 DMA 的相对摩尔比来控制的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)