(S)-2-[(S)-2-(2-{2-[(S)-2-Acetylamino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid amide | 132910-39-5

• 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: (S)-2-[(S)-2-(2-{2-[(S)-2-Acetylamino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid amide
• 英文别名: Ac-YGGFL-NH2；(2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-acetamido-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanamide
• CAS: 132910-39-5
• 化学式: C₃₀H₄₀N₆O₇
• 分子量: 596.684
• InChiKey: GFXHMPKMESGSMX-SDHOMARFSA-N

物化性质

• 沸点：
  1097.0±65.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  43
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  209
• 氢给体数：
  7
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-2-[(S)-2-(2-{2-[(S)-2-Acetylamino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid amide 在 potassium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  Exploiting azido-dichloro-triazine as a linker for regioselective incorporation of peptides through their N, O, S functional groups

  摘要：

  In the field of bioconjugation, linker development has witnessed massive growth in recent years. 2,4,6-Trichloro1,3,5-triazine (TCT) is a tridentate linker that can accommodate three distinct nucleophiles. Herein, the reaction of azido triazine derivatives with nucleophiles (amine, thiol and phenol) is studied. The replacement of first chlorine was performed at 0 degrees C while that of the last chlorine was achieved successfully at rt. As a proof of concept of this strategy with potential application in biological studies, pentapeptides (Ac-XGGFL-NH2 where X = Lys or Tyr or Cys) were reacted with 2-azido-4,6-dichlorotriazine to replace the first and second chlorine at 0 degrees C and at rt, respectively. The reactivity of 2-azido-4,6-dichlorotriazine was found to be similar for the alpha and epsilon amine group present in same peptide. These findings demonstrate the applicability of 2-azido-4,6-dichlorotriazine as a linker with potential further application in bioconjugation.

  DOI：

  10.1016/j.bioorg.2020.104334
• 作为产物：
  描述：

  N-乙酰-L-酪氨酸乙酯 以 乙醇 、 formamide 、 乙腈 为溶剂， 反应 120.0h， 生成 (S)-2-[(S)-2-(2-{2-[(S)-2-Acetylamino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid amide
  参考文献：
  名称：

  Gill, Iqbal; Vulfson, Evgeny N., Journal of the Chemical Society. Perkin transactions I, 1992, # 6, p. 667 - 668

  摘要：

  DOI：

文献信息

• Late-stage <i>gem</i>-difluoroallylation of phenol in bioactive molecules and peptides with 3,3-difluoroallyl sulfonium salts
  作者：Minqi Zhou、Jin-Xiu Ren、Xiao-Tian Feng、Hai-Yang Zhao、Xia-Ping Fu、Qiao-Qiao Min、Xingang Zhang

  DOI：10.1039/d3sc06302j

  日期：——

  method for the late-stage selective O-fluoroalkylation of tyrosine residues with a stable yet highly reactive fluoroalkylating reagent, 3,3-difluoroallyl sulfonium salts (DFASs), has been developed. The reaction proceeds in a mild basic aqueous buffer (pH = 11.6) with high efficiency, high biocompatibility, and excellent regio- and chemoselectivity. Various oligopeptides and phenol-containing bioactive

  已经开发出一种使用稳定且高反应性的氟烷基化试剂 3,3-二氟烯丙基锍盐 (DFAS) 对酪氨酸残基进行后期选择性O-氟烷基化的有效方法。该反应在温和的碱性水性缓冲液（pH = 11.6）中进行，具有高效率、高生物相容性以及优异的区域选择性和化学选择性。各种寡肽和含酚生物活性分子，包括碳水化合物和核苷，可以选择性地O-氟烷基化。 DFAS 添加的乙烯基和其他官能团可以成为连续修饰的有价值的连接体，显着扩展进一步生物共轭的化学空间。该方案的合成实用性已通过荧光标记的抗癌药物和 O-link 型 1,4,7,10-四氮杂环十二烷-N , N ', N , N'-四乙酸-酪氨酸3的合成得到证明。 -奥曲酸（DOTA-TATE），展示了该方法在药物化学和化学生物学中的前景。
• Solid-Phase Syntheses of Peptoids using Fmoc-ProtectedN-Substituted Glycines: The Synthesis of (Retro)Peptoids of Leu-Enkephalin and Substance P
  作者：John A. W. Kruijtzer、Lovina J. F. Hofmeyer、Wigger Heerma、Cornelis Versluis、Rob M. J. Liskamp

  DOI：10.1002/(sici)1521-3765(19980807)4:8<1570::aid-chem1570>3.0.co;2-2

  日期：1998.8.7

  A particularly interesting class of oligomeric peptidomimetics is formed by the peptoids, which consist of N-substituted glycine residues. A solid-phase synthesis method for peptoids is presented in which these residues are introduced using their Fmoc derivatives. This "monomer" method allowed the monitored synthesis of relatively large quantities of pure peptoids as well as the translation of, in principle, any peptide into the corresponding peptoid. The required Fmoc-substituted glycines were accessible by convenient synthesis, and a number of monomers including those containing side chains with functional groups have been synthesized. The use of Fmoc monomers also allowed implementation of a solid-phase synthesis protocol on a commercial peptide synthesizer. The method was exemplified by the solid-phase syntheses of the (retro)peptoids of Leu-enkephalin and substance P. Mass spectrometric studies of (retro)peptoids were essential for their characterization, and the presence of the B- and Y "- type ions allows sequence analysis. Substance P (retro)-peptoids were biologically active. HPLC analysis showed an increased hydrophobicity, and pepsin treatment resulted in greatly reduced degradation compared with the corresponding peptide.
• Exploiting azido-dichloro-triazine as a linker for regioselective incorporation of peptides through their N, O, S functional groups
  作者：Anamika Sharma、Ashish Kumar、Ayman El-Faham、Beatriz G. de la Torre、Fernando Albericio

  DOI：10.1016/j.bioorg.2020.104334

  日期：2020.11

  In the field of bioconjugation, linker development has witnessed massive growth in recent years. 2,4,6-Trichloro1,3,5-triazine (TCT) is a tridentate linker that can accommodate three distinct nucleophiles. Herein, the reaction of azido triazine derivatives with nucleophiles (amine, thiol and phenol) is studied. The replacement of first chlorine was performed at 0 degrees C while that of the last chlorine was achieved successfully at rt. As a proof of concept of this strategy with potential application in biological studies, pentapeptides (Ac-XGGFL-NH2 where X = Lys or Tyr or Cys) were reacted with 2-azido-4,6-dichlorotriazine to replace the first and second chlorine at 0 degrees C and at rt, respectively. The reactivity of 2-azido-4,6-dichlorotriazine was found to be similar for the alpha and epsilon amine group present in same peptide. These findings demonstrate the applicability of 2-azido-4,6-dichlorotriazine as a linker with potential further application in bioconjugation.
• Gill, Iqbal; Vulfson, Evgeny N., Journal of the Chemical Society. Perkin transactions I, 1992, # 6, p. 667 - 668
  作者：Gill, Iqbal、Vulfson, Evgeny N.

  DOI：——

  日期：——