N-(tert-butoxycarbonyl)-L-prolyl-L-valine benzyl ester | 53363-79-4

• 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: N-(tert-butoxycarbonyl)-L-prolyl-L-valine benzyl ester
• 英文别名: Boc-Pro-Val-OBzl；tert-butyl (2S)-2-[[(2S)-3-methyl-1-oxo-1-phenylmethoxybutan-2-yl]carbamoyl]pyrrolidine-1-carboxylate
• CAS: 53363-79-4
• 化学式: C₂₂H₃₂N₂O₅
• 分子量: 404.506
• InChiKey: JZHQOJADVCMOBD-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  84.94
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-L-prolyl-L-valine benzyl ester 在 三氟乙酸 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 2.0h， 生成 H-Pro-Val-OBzl
  参考文献：
  名称：

  Peptidomimetics for Targeting Protein–Protein Interactions between DOT1L and MLL Oncofusion Proteins AF9 and ENL

  摘要：

  MLL-fusion proteins, AF9 and ENL, play an essential role in the recruitment of DOT1L and the H3K79 hypermethylation of MLL target genes, which is pivotal for leukemogenesis. Blocking these interactions may represent a novel therapeutic approach for MLL-rearranged leukemia. Based on the 7 mer DOT1L peptide, a class of peptidomimetics was designed. Compound 21 with modified middle residues, achieved significantly improved binding affinities to AF9 and ENL, with K-D values of 15 nM and 57 nM, respectively. Importantly, 21 recognizes and binds to the cellular AF9 protein and effectively inhibits the AF9-DOT1L interactions in cells. Modifications of the N- and C-termini of 21 resulted in 28 with 2-fold improved binding affinity to AF9 and much decreased peptidic characteristics. Our study provides a proof-of-concept for development of nonpeptidic compounds to inhibit DOT1L activity by targeting its recruitment and the interactions between DOT1L and MLL-oncofusion proteins AF9 and ENL.

  DOI：

  10.1021/acsmedchemlett.8b00175
• 作为产物：
  描述：

  BOC-L-脯氨酸 、 L-缬氨酸苄酯对甲苯磺酸盐 在 N-甲基吗啉 、 氯甲酸乙酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-(tert-butoxycarbonyl)-L-prolyl-L-valine benzyl ester
  参考文献：
  名称：

  Shinoda, Ichizo; Fushimi, Akira; Kato, Hironobu, Agricultural and Biological Chemistry, 1985, vol. 49, # 9, p. 2587 - 2596

  摘要：

  DOI：

文献信息

• Molecular Capture and Conformational Change of Diketopiperazines Containing Proline Residues by Epigallocatechin-3-<i>O</i>-gallate in Water
  作者：Takashi Ishizu、Miku Tokunaga、Moeka Fukuda、Mana Matsumoto、Takeshi Goromaru、Soushi Takemoto

  DOI：10.1248/cpb.c21-00047

  日期：2021.6.1

  hydrophobicity of the side chain of the amino acid residue of cyclo(Pro-Xxx) led to a higher molecular capture ability. Furthermore, the molecular capture ability decreased when the side chain of the amino acid residue had a hydrophilic hydroxyl group. When diketopiperazine cyclo(Pro-Xxx), excluding cyclo(D-Pro-L-Ala), was taken into the hydrophobic space formed by the three aromatic A, B, and B′ rings of EGCg

  将二酮哌嗪环（Pro-Xxx）（Xxx：氨基酸残基）的水溶液添加到（-）-表没食子儿茶素-3- O的水溶液中-gallate (EGCg) 导致 EGCg 和环 (Pro-Xxx) 的复合物沉淀。使用 EGCg 的环 (Pro-Xxx) 的分子捕获能力通过与 EGCg 复合物的沉淀物中包含的环 (Pro-Xxx) 的量与所用的总环 (Pro-Xxx) 的量之比来评估。cyclo(Pro-Xxx) 氨基酸残基侧链的更强疏水性导致更高的分子捕获能力。此外，当氨基酸残基的侧链具有亲水性羟基时，分子捕获能力降低。当不包括环(D-Pro-L-Ala)的二酮哌嗪环(Pro-Xxx)被带入EGCg的三个芳香A、B和B'环形成的疏水空间中，形成复合物时，它们的构象保持在疏水空间中。基于核奥弗豪泽效应 (NOE) 测量，2 O 是轴向的，而环（L-Pro-L-Ala）是赤道的。当环(D-Pro-L-Ala)
• Structure of <i>N</i>-(<i>tert</i>-butoxycarbonyl)-<scp>L</scp>-prolyl-<scp>L</scp>-valylglycine hemihydrate
  作者：I. Tanaka、T. Ashida

  DOI：10.1107/s0567740880008242

  日期：1980.9.1
• CHATURVEDI, SANJEEV;BAHL, OM P., INT. J. PEPTIDE AND PROTEIN RES., 35,(1990) N, C. 133-140
  作者：CHATURVEDI, SANJEEV、BAHL, OM P.

  DOI：——

  日期：——