Cbz-Phe-D-Phe-OMe | 13122-87-7

• 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-Phe-D-Phe-OMe
• 英文别名: Z-L-Phe-D-Phe-OMe；N-Cbz-L-Phe-D-Phe-OMe；Z-Phe-D-Phe-OMe；ZPhe-DPheOMe；methyl (2R)-3-phenyl-2-[[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoate
• CAS: 13122-87-7
• 化学式: C₂₇H₂₈N₂O₅
• 分子量: 460.53
• InChiKey: QMKJDTHWFXXVPD-BJKOFHAPSA-N

物化性质

• 熔点：
  132-134 °C
• 沸点：
  687.7±55.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  Cbz-Phe-D-Phe-OMe 在 N-甲基吗啉 、 palladium on carbon 、 PyBop 、 氢气 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (2R)-2-[[(2S)-2-[[5-(diaminomethylidenecarbamoyl)-1H-pyrrole-2-carbonyl]amino]-3-phenylpropanoyl]amino]-3-phenylpropanoic acid
  参考文献：
  名称：

  在Phe-Phe延伸的胍基羰基吡咯烷基羧酸两性离子的自组装中的立体选择性自分选：形成两个具有明显不同稳定性的非对映异构二聚体。

  摘要：

  “二肽扩展的”胍基二羰基吡咯羧酸盐两性离子GCP-Phe-Phe 1在DMSO中形成稳定的二聚体。但是，二聚化是高度立体选择性的。仅形成同手性二聚体并且（L，L）。（L，L）二聚体（K（dim）> 10（5）M（-1））比非对映异构体更稳定10（3）倍（D，L）。（D，L）二聚体（K（dim）= 120 M（-1））。

  DOI：

  10.1039/c1cc12520f
• 作为产物：
  描述：

  N-苄氧羰基-L-苯丙氨酸 在 1-羟基苯并三唑 、 三乙胺 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 70.0h， 生成 Cbz-Phe-D-Phe-OMe
  参考文献：
  名称：

  HMDO-Promoted Peptide and Protein Synthesis in Ionic Liquids

  摘要：

  Hexamethyldisiloxane (HMDO) has been developed to efficiently promote the metal-free direct coupling of an amino function of one cysteine-free peptide or protein and a C-terminal thioester of the second peptide in ionic liquids. The amide-coupling reaction proceeds smoothly under mild conditions to afford the corresponding products in good to excellent yields (63-94%). Peptide couplings were also achieved using in-situ-generated thioesters by the thioesterification of oxo esters.

  DOI：

  10.1021/jo400797t

文献信息

• Enantioselection in peptide bond formation
  作者：Roger R. Hill、David Birch、Graham E. Jeffs、Michael North

  DOI：10.1039/b211914e

  日期：2003.3.13

  Selectivity in abiotic condensations of amino acids remains controversial and stereochemically little explored. We find that competitive activated couplings of N-acyl derivatives of glycine, alanine, valine, proline and phenylalanine with binary, ternary and quaternary mixtures of amides and esters of the same group of amino acids show little selectivity among the reactants, except with respect to configuration, where a consistent and significant preference for heterochiral outcomes, mostly >80%, is observed. One possible explanation of this selectivity predicts a predisposition to homochiral coupling under conditions that would require the two carboxyl functions to be co-facial in the activated complex.

  无机物促成的氨基酸缩聚反应中选择性仍然备受争议，而立体化学方面的研究甚少。我们发现，以酰胺和酯组成的双组分、三组分以及四组分混合物为底物，对甘氨酸、丙氨酸、缬氨酸、脯氨酸和苯丙氨酸的N-酰基衍生物进行竞争性活化偶联的反应中，产物在底物分子层面选择性较低，但对映异构选择性较高，选择性系数大多大于80%。此类反应中优先生成异手性产物的一种可能的解释是，在两个羧基必须共面的活化复合物中，同手性偶联具有倾向性。
• Catalytic role of PPh3 and its polymer bound analog in the amidation of carboxylic acids mediated by 2,4,6-trichloro-1,3,5-triazine
  作者：Chuthamat Duangkamol、Subin Jaita、Sirilak Wangngae、Wong Phakhodee、Mookda Pattarawarapan

  DOI：10.1016/j.tetlet.2015.07.012

  日期：2015.8

  The catalytic role of PPh3 and its polymer bound analog was investigated in the 2,4,6-trichloro-1,3,5-triazine (TCT) mediated amidation of carboxylic acids. In the presence of inorganic bases which were inert toward TCT, carboxylic acids rapidly reacted with amines to afford amides in good to excellent yields. The described method also enabled the synthesis of optically active protected dipeptides

  在2,4,6-三氯-1,3,5-三嗪（TCT）介导的羧酸酰胺化反应中，研究了PPh 3及其与聚合物结合的类似物的催化作用。在对TCT呈惰性的无机碱的存在下，羧酸与胺迅速反应，以良好或优异的收率得到酰胺。所描述的方法还能够在没有外消旋的情况下合成旋光保护的二肽。根据31 P NMR研究证实，在PPh 3催化的酸活化过程中形成了三嗪基氯化chloride 。
• Facile Synthesis of Cyclic Dipeptides and Detection of Racemization
  作者：Toshihisa Ueda、Morinobu Saito、Tetsuo Kato、Nobuo Izumiya

  DOI：10.1246/bcsj.56.568

  日期：1983.2

  Several cyclic dipeptides were synthesized by refluxing methanolic solution of dipeptide methyl esters in high yield and purity. Cyclic dipeptides prepared by the Fischer method, the Nitecki method, and the present methanol-reflux method were compared with respect to yield and optical purity. The methanol-reflux method usually gave good results. High-performance liquid chromatography was effectively applied to detect racemization.

  通过回流二肽甲酯的甲醇溶液，合成了几个高产率和高纯度的环状二肽。通过Fischer法、Nitecki法和当前的甲醇回流法准备的环状二肽，在产率和光学纯度方面进行了比较。甲醇回流法通常能得到良好的结果。高效液相色谱法有效地应用于检测外消旋化。
• Hexapeptide amides
  申请人：Sterling Drug Inc.

  公开号：US04472305A1

  公开（公告）日：1984-09-18

  N-Terminal L-prolyl or D-prolyl hexapeptide amides useful as Substance P agonists and/or antagonists and as analgesics and/or antihypertensives and a process for preparing them are disclosed.

  本发明公开了N-端L-脯氨酰或D-脯氨酰六肽酰胺，其可用作物质P激动剂和/或拮抗剂，以及作为镇痛剂和/或降压剂，还公开了一种制备它们的方法。
• α-Chymotrypsin-catalyzed peptide synthesis in frozen aqueous solution using N-protected amino acid carbamoylmethyl esters as acyl donors
  作者：Sayed Mohiuddin Abdus Salam、Ken-ichi Kagawa、Katsuhiro Kawashiro

  DOI：10.1016/j.tetasy.2005.10.042

  日期：2006.1

  A kinetically controlled peptide synthesis catalyzed by alpha-chymotrypsin was performed in frozen aqueous solution (ice, -24 degrees C). The yield of the peptide was significantly improved by the use of the carbamoylmethyl (Cam) ester as the acyl donor instead of the conventional ethyl ester. The peptide yield increased up to ca. 90% when N-benzyloxycarbonyl (CBZ)-Phe-OCam and H-Phe-NH2 were used as the acyl donor and nucleophile, respectively. Such an improvement of the peptide yield in ice was also observed in the coupling of other CBZ-amino acid Cam esters as acyl donors. Furthermore, this approach was applied to the synthesis of peptides containing D-amino acids. The peptides such as CBZ-D-Phe-Phe-NH2, CBZ-Phe-D-Phe-NH2 and CBZ-D-Phe-D-Phe-NH2 were also obtained in excellent to moderate yields in ice. A high diastereoselectivity towards the L-L peptide was observed when the racemic amino acid Cam ester was used as the acyl donor in ice. (c) 2005 Elsevier Ltd. All rights reserved.