Cbz-L-Phe-L-Thr-OH

• 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-L-Phe-L-Thr-OH
• 英文别名: (2S,3R)-3-hydroxy-2-[[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]butanoic acid
• 化学式: C₂₁H₂₄N₂O₆
• 分子量: 400.431
• InChiKey: LOSOBOMQDAAZOK-JLSDUUJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Cbz-L-Phe-L-Thr-OH 在 palladium on activated charcoal 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 16.0h， 生成 N-(L-phenylalanyl)-O-((tert-butoxycarbonyl)glycyl)-L-threonine
  参考文献：
  名称：

  O-酰基异肽通过 8 元和 11 元环状过渡态化学连接

  摘要：

  已合成未保护的 O-酰化丝氨酸和 O-酰化苏氨酸异肽，并研究了它们通过 O 到 N 端转移转化为天然三肽和四肽的过程。实验和计算表明，涉及 8 元和 11 元循环过渡态的连接比分子间交叉连接更有利。

  DOI：

  10.3998/ark.5550190.p008.632
• 作为产物：
  描述：

  N-苄氧羰基-L-苯丙氨酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 4.75h， 生成 Cbz-L-Phe-L-Thr-OH
  参考文献：
  名称：

  Synthesis, molecular docking and anticancer studies of peptides and iso-peptides

  摘要：

  Chiral peptides and iso-peptides were synthesized in excellent yield by using benzotriazole mediated solution phase synthesis. Benzotriazole acted both as activating and leaving group, eliminating frequent use of protection and subsequent deprotection. The procedure was based on the hypothesis that epimerization should be suppressed in solution due to a faster coupling rate than SPPS. All the synthesized peptides complied with Lipinski's Ro5 except for the rotatable bonds. Inhibition of cell proliferation of cancer cell lines is one of the most commonly used methods to study the effectiveness of any anticancer agents. Synthesized peptides and iso-peptides were tested against three cancer cell lines (MCF-7, MDA-MB 231) to determine their anti-proliferative potential. NF kappa B was also determined. Molecular docking studies were also carried out to complement the experimental results. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.05.020

文献信息

• Convenient green preparation of dipeptides using unprotected α-amino acids
  作者：Tetsuya Ezawa、Seunghee Jung、Yuya Kawashima、Takuya Noguchi、Nobuyuki Imai

  DOI：10.1016/j.tetasy.2016.11.009

  日期：2017.1

  Dipeptides and amides were obtained in high yields from N-carbobenzyloxy a-amino acids and 3-phenylpropanoic acid with unprotected a-amino acids via the corresponding mixed carbonic carboxylic anhydrides using ethyl chloroformate and triethylamine by an ecological and convenient method in which the protection of C-terminals is not needed. (C) 2016 Elsevier Ltd. All rights reserved.
• Solid-Phase Synthesis of 1,3-Azole-Based Peptides and Peptidomimetics
  作者：Eric Biron、Jayanta Chatterjee、Horst Kessler

  DOI：10.1021/ol0607645

  日期：2006.5.1

  [graphics]We report highly efficient two-step procedures for the synthesis of 1,3-oxazole-, thiazole-, and imidazole- containing peptides on solid phase from dipeptides composed of C-terminal threonine, serine, cysteine, or diaminopropionic acid by using different cyclodehydration procedures followed or preceded by oxidation. The methods are compatible with Fmoc solid-phase peptide synthesis conditions and with N-Fmoc, N-Boc, N-Cbz, and N-Alloc protecting groups.
• Synthesis, molecular docking and anticancer studies of peptides and iso-peptides
  作者：Farukh Jabeen、Siva S. Panda、Tamara P. Kondratyuk、Eun-Jung Park、John M. Pezzuto、Ihsan-ul-haq、C. Dennis Hall、Alan R. Katritzky

  DOI：10.1016/j.bmcl.2015.05.020

  日期：2015.8

  Chiral peptides and iso-peptides were synthesized in excellent yield by using benzotriazole mediated solution phase synthesis. Benzotriazole acted both as activating and leaving group, eliminating frequent use of protection and subsequent deprotection. The procedure was based on the hypothesis that epimerization should be suppressed in solution due to a faster coupling rate than SPPS. All the synthesized peptides complied with Lipinski's Ro5 except for the rotatable bonds. Inhibition of cell proliferation of cancer cell lines is one of the most commonly used methods to study the effectiveness of any anticancer agents. Synthesized peptides and iso-peptides were tested against three cancer cell lines (MCF-7, MDA-MB 231) to determine their anti-proliferative potential. NF kappa B was also determined. Molecular docking studies were also carried out to complement the experimental results. (C) 2015 Elsevier Ltd. All rights reserved.
• Chemical ligation from O-acyl isopeptides via 8- and 11-membered cyclic transition states
  作者：Siva S. Panda、Mohamed Elagawany、Hadi M. Marwani、Eray Çalɪşkan、Mirna El-Katib、Alexander Oliferenko、Khalid A Alamry、Alan R Katritzky

  DOI：10.3998/ark.5550190.p008.632

  日期：——

  Unprotected O-acylated serine and O-acylated threonine isopeptides have been synthesized, and their conversion to native tripeptides and tetrapeptides by O- to N-terminus transfer investigated. Ligations involving 8- and 11-membered cyclic transition states are shown experimentally and computationally to be more favorable than intermolecular cross-ligations.

  已合成未保护的 O-酰化丝氨酸和 O-酰化苏氨酸异肽，并研究了它们通过 O 到 N 端转移转化为天然三肽和四肽的过程。实验和计算表明，涉及 8 元和 11 元循环过渡态的连接比分子间交叉连接更有利。