Pro-Lys-Lys-Lys-Arg-Lys-Val-Gly-NH-NH2 | 1370733-04-2

• 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: Pro-Lys-Lys-Lys-Arg-Lys-Val-Gly-NH-NH2
• 英文别名: PKKKRKVG
• CAS: 1370733-04-2
• 化学式: C₄₂H₈₃N₁₇O₈
• 分子量: 954.23
• InChiKey: JNOHVTDOOYVPEN-SLJYAKFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.81
• 重原子数：
  67.0
• 可旋转键数：
  36.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  436.83
• 氢给体数：
  17.0
• 氢受体数：
  15.0

反应信息

• 作为产物：
  描述：

  肼基甲酸叔丁酯 、 Boc-Pro-Lys(Boc)-Lys(Boc)-Arg(Pbf)-Lys(Boc)-Val-Gly-OH 在 O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三异丙基硅烷 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 6.0h， 生成 Pro-Lys-Lys-Lys-Arg-Lys-Val-Gly-NH-NH2
  参考文献：
  名称：

  Synthesis of GnRH analogues and their application in targeted gene delivery systems

  摘要：

  A set of GnRH analogues containing the nuclear localization signal (NLS) of the SV-40 virus was synthesized using solid phase peptide synthesis and chemical ligation techniques. Selective chemical ligation was achieved through hydrazone formation upon the interaction of NLS hydrazide and GnRH analogue modified with pyruvic acid. The efficiency of the synthesized compounds was demonstrated in experiments on transfection of various human cancer cell lines with reporter luciferase and beta-galactosidase genes, as well as suicide thymidine kinase gene of HSV-1. Selectivity of the peptide-DNA complex effect on cancer cells is achieved as a result of its penetration through the cell membrane via GnRH receptor-mediated endocytosis pathway.

  DOI：

  10.1134/s1068162012010190

文献信息

• Convenient method of peptide hydrazide synthesis using a new hydrazone resin
  作者：Pavel S. Chelushkin、Ksenia V. Polyanichko、Maria V. Leko、Marina Yu. Dorosh、Thomas Bruckdorfer、Sergey V. Burov

  DOI：10.1016/j.tetlet.2014.12.056

  日期：2015.1

  Peptide hydrazides can be easily synthesized using a new hydrazone resin, obtained via acylation of aminomethyl polystyrene by Fmoc-hydrazone of pyruvic acid. It was shown that the hydrazone linker is completely stable in the course of standard Fmoc SPPS. Moreover, it can tolerate a treatment with 5% TFA/DCM thus permitting selective removal of Mtt or related acid-labile protecting groups. Subsequent

  可以使用新型can树脂轻松合成肽酰肼，这种resin树脂是通过丙酮酸的Fmoc-zone对氨基甲基聚苯乙烯进行酰化而获得的。结果表明，link连接基在标准Fmoc SPPS的过程中是完全稳定的。而且，它可以耐受5％TFA / DCM的处理，从而允许选择性除去Mtt或相关的酸不稳定的保护基。随后施加含有净TFA的裂解混合物，可以以合理的产率和纯度获得所需的肽。可以使用peptide连接技术将合成的肽酰肼用作构建基，以与不同的载体分子偶联。