Ac-D-F-D-A-OMe | 27842-12-2

• 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: Ac-D-F-D-A-OMe
• 英文别名: Ac-D-Phe-D-Ala-OMe；methyl (2R)-2-[[(2R)-2-acetamido-3-phenylpropanoyl]amino]propanoate
• CAS: 27842-12-2
• 化学式: C₁₅H₂₀N₂O₄
• 分子量: 292.335
• InChiKey: VKFDJBFIVUKVCL-ZWNOBZJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  AcΔPheAlaOH 在 Rh[(+)-DIOP]Cl 盐酸 、 氢气 作用下， 反应 48.0h， 生成 Ac-D-F-D-A-OMe
  参考文献：
  名称：

  使用外消旋混合物通过手性合成进行部分拆分

  摘要：

  具有手性前手性中心的化合物的外消旋混合物可以与手性试剂部分反应; 形成非对映体产物，并且将原料动力学拆分。讨论了反应产物和回收的原料的相对量与对映体过量之间的关系。给出了由铑二氮杂配合物催化的外消旋AcΔPheAlaOMe不对称氢化的应用。

  DOI：

  10.1016/s0040-4020(01)98803-9

文献信息

• Asymmetric Hydrogenation of Dehydrodipeptides with Rhodium(I)–Chiral Diphosphinites. Selective (<i>S</i>,<i>S</i>)- and (<i>R</i>,<i>R</i>)-Product Formation by Double Asymmetric Induction
  作者：Masanobu Yatagai、Takamichi Yamagishi、Mitsuhiko Hida

  DOI：10.1246/bcsj.57.823

  日期：1984.3

  stereoselectivities, depending on the chiral center of the substrates. This result was ascribed to the electrostatic interaction between the ligand and substrate. POP’s without ω-(dimethylamino)alkyl group gave (R,R)-product for (R)-substrate in a high stereoselectivity by the steric effect between the ligand and substrate, while for (S)-substrate, (S,S)-product was obtained in a low stereoselectivity.

  在脱氢二肽的氢化中，使用含有吡咯烷部分的 Rh(I)-手性二亚膦酸盐 (POP) 的催化剂检查了底物 ((S) 或 (R)) 的手性中心对不对称诱导的影响。具有 ω-(二甲氨基) 烷基的 POP 的催化剂显示出极大的双不对称诱导，以高立体选择性产生 (S,S)- 或 (R,R)- 产物，具体取决于底物的手性中心。该结果归因于配体和底物之间的静电相互作用。没有ω-（二甲氨基）烷基的POPs通过配体和底物之间的空间效应以高立体选择性为（R）-底物提供（R，R）-产物，而对于（S）-底物，（S，S） -产物以低立体选择性获得。
• 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.
• EL-BABA, S.;POULIN, J. -C.;KAGAN, H. B., TETRAHEDRON, 1984, 40, N 21, 4275-4284
  作者：EL-BABA, S.、POULIN, J. -C.、KAGAN, H. B.

  DOI：——

  日期：——
• Partial resolution through chiral synthesis using a racemic mixture
  作者：Sana El-Baba、Jean-Claude Poulin、Henri B. Kagan

  DOI：10.1016/s0040-4020(01)98803-9

  日期：——

  A racemic mixture of a compound bearing a reactive prochiral center can partially react with a chiral reagent ; diastereomeric products are formed and the starting material is kinetically resolved. The relationships between the relative amounts and the enantiomeric excesses of reaction products and recovered starting material are discussed. Applications are given for asymmetric hydrogenation of racemic

  具有手性前手性中心的化合物的外消旋混合物可以与手性试剂部分反应; 形成非对映体产物，并且将原料动力学拆分。讨论了反应产物和回收的原料的相对量与对映体过量之间的关系。给出了由铑二氮杂配合物催化的外消旋AcΔPheAlaOMe不对称氢化的应用。