Cbz-Gly-D-Phe-Val-OMe | 113266-24-3

• 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: Cbz-Gly-D-Phe-Val-OMe
• 英文别名: Z-Gly-(D)Phe-Val-OMe；Z-Gly-D-Phe-Val-OCH3；Z-Gly-D-Phe-Val-OMe；Z-Gly-Phe-Val-OMe；methyl (2S)-3-methyl-2-[[(2R)-3-phenyl-2-[[2-(phenylmethoxycarbonylamino)acetyl]amino]propanoyl]amino]butanoate
• CAS: 113266-24-3
• 化学式: C₂₅H₃₁N₃O₆
• 分子量: 469.538
• InChiKey: MWAZJGWQMLRJCN-IRLDBZIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-苄氧羰基甘氨酰-L-苯丙氨酸 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 2.5h， 生成 Cbz-Gly-D-Phe-Val-OMe
  参考文献：
  名称：

  新型与水相容的脱水剂DPTF

  摘要：

  羧酸和胺的脱水反应形成酰胺键是通过使用一种新型的水相容性脱水剂2,2-二氯-5-（2-苯乙基）-4-（三甲基甲硅烷基）-3-呋喃酮（DPTF）。还描述了这种新试剂在肽键形成中的应用。

  DOI：

  10.1016/0040-4039(96)01712-1

文献信息

• 1-Ethyl 2-Halopyridinium Salts, Highly Efficient Coupling Reagents for Hindered Peptide Synthesis both in Solution and the Solid-Phase
  作者：Peng Li、Jie-Cheng Xu

  DOI：10.1016/s0040-4020(00)00657-8

  日期：2000.10

  proved to be very effective for the synthesis of hindered peptides containing N-methylated or Cα,Cα-dialkylated amino acid residues. HPLC monitoring of model reactions indicated that these pyridinium salts demonstrated higher reactivities, lower racemization than the commonly used halogenated uronium and phosphonium salts. The efficiency of these pyridinium type coupling reagents was further proved by the

  1-乙基-2-卤代吡啶鎓盐，BEP，FEP，BEPH和FEPH，合成并证明是含有受阻的肽的合成是非常有效的Ñ甲基化的或Ç α，Ç α-二烷基化的氨基酸残基。HPLC对模型反应的监测表明，与通常使用的卤化铀盐和phoSPho盐相比，这些吡啶鎓盐具有更高的反应活性和更低的消旋性。通过合成一系列受阻的寡肽和活性酯，具有良好的收率和方便的后处理，进一步证明了这些吡啶鎓类偶联剂的效率。使用这些吡啶鎓盐还成功合成了环孢菌素A（CsA）的8-11四肽片段和Dolastatin 15的五肽部分。这些吡啶鎓类偶联剂对SPPS的效率还通过CsA的极受阻碍的8-11肽段和CsO的线性十一肽的固相合成证明。1 H NMR，IR和HPLC。提出主要的反应性中间体是N-保护的氨基酸或肽的相应的酰卤和酰氧基吡啶鎓盐。
• Ethyl 2-Cyano-2-(hydroxyimino)acetate (Oxyma): An Efficient and Convenient Additive Used with Tetramethylfluoroformamidinium Hexafluorophosphate (TFFH) to Replace 1-Hydroxybenzotriazole (HOBt) and 1-Hydroxy-7-azabenzotriazole (HOAt) during Peptide Synthesis
  作者：Sherine N. Khattab

  DOI：10.1246/bcsj.20100075

  日期：2010.11.15

  The appropriateness of ethyl 2-cyano-2-(hydroxyimino)acetate (Oxyma) as a substitute for benzotriazole-based additives, for use in the TFFH approach for peptide synthesis, is discussed in terms of ...

  讨论了 2-氰基-2-（羟基亚氨基）乙酸乙酯 (Oxyma) 作为苯并三唑类添加剂替代品的适用性，用于肽合成的 TFFH 方法，从以下方面进行讨论。
• PS-IIDQ: a supported coupling reagent for efficient and general amide bond formation
  作者：Eric Valeur、Mark Bradley

  DOI：10.1016/j.tet.2007.06.019

  日期：2007.9

  Polystyrene-IIDQ, a polymer-supported coupling reagent, was synthesized in three steps from Merrifield resin in 86% overall conversion. This reagent efficiently coupled carboxylic acids to amines in good yields and high purities, required no pre-activation step, and was tolerant of the order of reagent addition. PS-IIDQ was observed to be more efficient than polymer-supported carbodiimides (PS-EDC and

  由Merrifield树脂分三步合成了聚合物支撑的偶联剂聚苯乙烯-IIDQ，总转化率为86％。该试剂以高收率和高纯度将羧酸有效地偶联到胺上，不需要预活化步骤，并且可以耐受试剂添加的顺序。观察到PS-IIDQ比聚合物负载的碳二亚胺（PS-EDC和PS-DCC）更有效，并且在一般的酰胺键形成（包括苯胺和受阻底物偶联）方面，其收率高于HATU。用五种羧酸和九种胺（包括苯胺和仲胺）进行评估时，PS-IIDQ的平均分离收率为73％。
• New and Highly Efficient Immonium Type Peptide Coupling Reagents: Synthesis, Mechanism and Application
  作者：Peng Li、Jie-Cheng Xu

  DOI：10.1016/s0040-4020(00)00365-3

  日期：2000.6

  A series of novel immonium type coupling reagents BOMI, BDMP, BPMP, DOMP, SOMP, FOMP and AOMP were designed and synthesized. It was shown that most of these reagents were more efficient in peptide synthesis than conventional methods due to the advantages of high reactivity, low racemization and good yields. The reaction mechanism was proposed and studied by 1H NMR, IR, UV and HPLC.

  设计合成了一系列新型的铵型偶联剂BOMI，BDMP，BPMP，DOMP，SOMP，FOMP和AOMP。结果表明，由于具有高反应活性，低外消旋性和高收率的优势，大多数这些试剂在肽合成方面比常规方法更有效。提出了反应机理，并通过1 H NMR，IR，UV和HPLC进行了研究。
• S-(2-Pyrimidinyl)- and S-(2-(4,6-dimethylpyrimidinyl))-1,1,3,3-tetramethylthiouronium hexafluorophosphates: novel reagents for in situ peptide coupling
  作者：Philip Garner、Özge Şeşenoğlu、H. Ümit Kaniskan

  DOI：10.1016/j.tetlet.2005.11.067

  日期：2006.1

  Two new reagents for in situ peptide coupling based on the 2-mercaptopyrimidine core have been developed. The readily prepared thiouronium salts were found to promote both peptide and segment coupling efficiently with low racemization/epimerization levels.

  已经开发了两种基于2-巯基嘧啶核的用于原位肽偶联的新试剂。发现容易制备的硫脲鎓盐以低消旋化/表观异构化水平有效地促进肽和链段偶联。