N-Ac-D-Phe-D-Trp-OMe | 76327-09-8

• 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-Ac-D-Phe-D-Trp-OMe
• 英文别名: Ac-D-F-D-W-OMe；N-(N-Acetyl-D-phenylalanyl)-D-tryptophan methyl ester；methyl (2R)-2-[[(2R)-2-acetamido-3-phenylpropanoyl]amino]-3-(1H-indol-3-yl)propanoate
• CAS: 76327-09-8
• 化学式: C₂₃H₂₅N₃O₄
• 分子量: 407.469
• InChiKey: NIXPIONKGWROJJ-NHCUHLMSSA-N

物化性质

• 沸点：
  734.9±60.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  100
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-乙酰-D-苯丙氨酸 、 D-色氨酸甲酯 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以84%的产率得到N-Ac-D-Phe-D-Trp-OMe
  参考文献：
  名称：

  合成肽受体模拟物：在非共价分子印迹聚合物中的高度立体选择性识别

  摘要：

  已在针对N -Ac-L-Phe-L-Trp-OMe制备的分子印迹聚合物（MIP）中研究了配体受体识别。使用聚合物作为手性HPLC固定相评估了基于非离子非共价相互作用的识别。对映体，对映体和非对映体配体的选择性最高，对映体分离因子高达17.8。一系列相关结构与MIP受体位点的相互作用提供了有关其性质和识别机制的见解。

  DOI：

  10.1016/0957-4166(94)80027-8

文献信息

• Aminolytic reaction catalyzed by d-stereospecific amidohydrolases from Streptomyces spp
  作者：Jiro Arima、Hitomi Ito、Tadashi Hatanaka、Nobuhiro Mori

  DOI：10.1016/j.biochi.2011.04.020

  日期：2011.9

  From investigation of 2000 soil isolates, we identified two serine-type amidohydrolases that can hydrolyze D-aminoacyl derivatives from the culture supernatant of Streptomyces species 82F2 and 83D12. The enzymes, redesignated as 82F2-DAP and 83D12-DAP, were purified for homogeneity and characterized. Each enzyme had molecular mass of approximately 40 kDa, and each showed moderate stability with respect to temperature and pH. Among hydrolytic activities toward D-aminoacyl-pNAs, the enzymes showed strict specificity toward D-Phe-pNA, but showed broad specificity toward D-aminoacyl esters. The specific activity for D-Phe-pNA hydrolysis of 82F2-DAP was ten-fold higher than that of 83D12-DAP. As a second function, each enzyme showed peptide bond formation activity by its function of aminolysis reaction. Based on results of D-Phe D-Phe synthesis under various conditions, we propose a reaction mechanism for D-Phe D-Phe production. Furthermore, the enzymes exhibited peptide elongation activity, producing oligo homopeptide in a one-pot reaction. We cloned the genes encoding each enzyme, which revealed that the primary structure of each enzyme showed 30-60% identity with those of peptidases belonging to the clan SE, S12 peptidase family categorized as serine peptidase with D-stereospecificity. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Synthetic peptide receptor mimics: highly stereoselective recognition in non-covalent molecularly imprinted polymers
  作者：Olof Ramström、Ian A. Nicholls、Klaus Mosbach

  DOI：10.1016/0957-4166(94)80027-8

  日期：1994.4

  Ligand-receptor recognition has been studied in a molecularly imprinted polymer (MIP) prepared against N-Ac-L-Phe-L-Trp-OMe. The non-ionic non-covalent interaction based recognition was evaluated using the polymers as chiral HPLC stationary phases. Marked regio-, enantio- and diastereo- ligand selectivity were demonstrated with enantiomer separation factors of up to 17.8. The interaction of a series of

  已在针对N -Ac-L-Phe-L-Trp-OMe制备的分子印迹聚合物（MIP）中研究了配体受体识别。使用聚合物作为手性HPLC固定相评估了基于非离子非共价相互作用的识别。对映体，对映体和非对映体配体的选择性最高，对映体分离因子高达17.8。一系列相关结构与MIP受体位点的相互作用提供了有关其性质和识别机制的见解。