Z-Pro-Leu-Gly-N-succinimidyl ester | 68427-07-6

• 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: Z-Pro-Leu-Gly-N-succinimidyl ester
• 英文别名: Cbz-Pro-Leu-Gly-OSu；benzyl (2S)-2-[[(2S)-1-[[2-(2,5-dioxopyrrolidin-1-yl)oxy-2-oxoethyl]amino]-4-methyl-1-oxopentan-2-yl]carbamoyl]pyrrolidine-1-carboxylate
• CAS: 68427-07-6
• 化学式: C₂₅H₃₂N₄O₈
• 分子量: 516.551
• InChiKey: QEVLMQKJTUVWID-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  151
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Z-Pro-Leu-Gly-N-succinimidyl ester 在 氢溴酸 、 碳酸氢钠 作用下， 以 乙二醇二甲醚 、 水 、 溶剂黄146 为溶剂， 生成 (S)-1-(2-{(S)-4-Methyl-2-[((S)-pyrrolidine-2-carbonyl)-amino]-pentanoylamino}-acetyl)-pyrrolidine-2-carboxylic acid ({4-[bis-(2-chloro-ethyl)-amino]-phenylcarbamoyl}-methyl)-amide
  参考文献：
  名称：

  Synthesis and in vitro evaluation of macromolecular antitumour derivatives based on phenylenediamine mustard

  摘要：

  Poly- [N-(2-hydroxyethyl)-L-glutamine] (PHEG) and poly(ethylene glycol) (PEG)-grafted PHEG conjugates of NN-di(2-chloroethyl)-4phenylenediamine mustard (PDM) were synthetised. A collagenase-sensitive oligopeptide spacer was selected to link the cytotoxic agent PDM onto the polymeric carrier. First, the oligopeptide-drug conjugate, L-pro-L-leu-gly-L-pro-gly-PDM, was prepared. In a second step, the low molecular weight PDM derivative and PEG-NH2 were coupled to a N,N-disuccinimidylcarbonate activated PHEG. Dynamic laser light scattering measurements indicated the formation of aggregates. The presence of human serum albumin had no significant effect on the diameter of the conjugates. The hydrolytic stability of the conjugates was investigated in buffer solutions. The conjugates showed an improved stability compared to the parent nitrogen mustard. The enzymatic degradation studies of the polymeric conjugates were performed in the presence of collagenase type IV (Clostridiopeptidase A; EC 3.4.24.3), cathepsin B (EC 3.4.22.1), cathepsin D (EC 3.4.23.5) and tritosomes. Only the bacterial collagenase type IV was able to cleave the spacer releasing free PDM and its peptidyl derivative, gly-L-pro-gly-PDM. The in vitro cytotoxicity of the conjugates was evaluated against HT1080 fibrosarcoma cells and MDA adenocarcinoma cells. All conjugates showed low toxicity towards these cell lines. (C) 2004 Published by Elsevier B.V.

  DOI：

  10.1016/j.ejps.2004.09.006
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 Z-Pro-Leu-Gly-OH 在 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 以67.7%的产率得到Z-Pro-Leu-Gly-N-succinimidyl ester
  参考文献：
  名称：

  C-末端 18F-氟乙基酰胺化以 [Gly-OH9] 催产素为例

  摘要：

  受保护的九肽 Boc–Cys–Tyr(tBu)–Ile–Gln(Mtt)–Asn(Mtt)–Cys–Pro–Leu–Gly–OH 的酸功能的无载体添加 (nca) 18F-氟乙基酰胺化描述了形成标记的肽激素衍生物[Gly-(2-[18F]氟乙基)NH9]-催产素。使用与催产素 C 端序列相同的受保护三肽详细说明标记条件。辅基 nca 2-[18F] 氟乙胺是通过穴状化合物介导的 nca 18F-氟化在 DMSO（RCY：约 60%）中 N-Boc-2-（对甲苯磺酰氧基）乙胺和随后脱保护合成的，放射化学产率为46±5%。[18F]氟乙胺与Z-Pro-Leu-Gly-OH在偶联剂TBTU或模型三肽的活化酯存在下反应。活化酯方法以及在 TBTU 存在下的缩合产生⩾ 90% 的 18F-氟乙基酰胺化三肽。TBTU 介导的 nca 2-[18F] 氟-乙胺与受保护的催产素的 C 端游离酸基团的缩合得到约

  DOI：

  10.1002/jlcr.547