D-methyl 2-trifluoromethanesulfonyl-3-phenyllactate | 84028-86-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: D-methyl 2-trifluoromethanesulfonyl-3-phenyllactate
• 英文别名: (R)-3-phenyl-2-trifluoromethanesulfonyloxypropionic acid methyl ester；methyl (2R)-3-phenyl-2-{[(trifluoromethyl)sulfonyl]oxy}propanoate；(R)-methyl 3-phenyl-2-(((trifluoromethyl)sulfonyl)oxy)propanoate；methyl (R)-3-phenyl-2-((trifluoromethylsulfonyl)oxy)propanoate；(R)-2-(Trifluoromethylsulfonyloxy)-3-phenylpropanoic acid methyl ester；methyl (2R)-3-phenyl-2-(trifluoromethylsulfonyloxy)propanoate
• CAS: 84028-86-4
• 化学式: C₁₁H₁₁F₃O₅S
• 分子量: 312.267
• InChiKey: XFMNYRKEHCMITR-SECBINFHSA-N

物化性质

• 沸点：
  348.0±42.0 °C(Predicted)
• 密度：
  1.423±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  D-methyl 2-trifluoromethanesulfonyl-3-phenyllactate 在 sodium hydroxide 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 (S)-2-hydrazinyl-3-phenylpropanoic acid
  参考文献：
  名称：

  Ribosome-Mediated Incorporation of Hydrazinophenylalanine into Modified Peptide and Protein Analogues

  摘要：

  (S)-alpha-Hydrazinophenylalanyl-tRNA(Phe), an amino acyl-tRNA derivative containing the unnatural amino acid (S)-alpha-hydrazinophenylalanine, was prepared in an effort to examine the stereochemical requirements of the A-site of the ribosome during in vitro protein synthesis. The (S)-alpha-hydrazinophenylalanine moiety was of interest because it contains two nucleophilic centers, the secondary nitrogen attached to Ca, which is normally acylated during the course of peptide bond formation, and the sterically less hindered primary nitrogen. To determine the position of acylation, (S)-alpha-hydrazinophenylalanyl-tRNA(Phe) was tested in an Escherichia coli in vitro protein biosynthesizing system lacking elongation factor G, such that only dipeptide products were formed. The dipeptide product mixture was analyzed by HPLC in direct comparison with authentic synthetic standards. The dipeptide assay utilizing (S)-alpha-hydrazinophenylalanyl-tRNA(Phe) as the A-site tRNA established that the analogue functioned well as an acceptor tRNA; HPLC analysis of the products showed that both dipeptides were formed in approximately equal amounts. When attached to a suppressor tRNA transcript, (S)-alpha-hydrazinophenylalanine was also incorporated into position 27 of dihydrofolate reductase in an E. coli protein synthesizing system by readthrough of a nonsense codon. This finding expands the currently accepted model of peptide bond formation at the ribosome and adds to the repertoire of peptide-like products shown to form at the peptidyltransferase center of the ribosome.

  DOI：

  10.1021/ja974066e
• 作为产物：
  描述：

  D-苯丙氨酸 在 2,6-二甲基吡啶 、 水 、 potassium carbonate 、 溶剂黄146 、 sodium nitrite 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 D-methyl 2-trifluoromethanesulfonyl-3-phenyllactate
  参考文献：
  名称：

  四氢哒嗪二酮限制肽的固相合成

  摘要：

  报道了衍生自骨架胺化肽的四氢哒嗪-3,6-二酮 (Tpd) 肽模拟物的设计和固相合成。所描述的协议的特点是手性 α-肼酸的合成适用于化学选择性掺入不断增长的肽链。在裂解过程中酸催化环化形成 Tpd 环以良好的产率和纯度提供目标肽模拟物。Tpd 掺入的范围通过合成具有亲核/亲电侧链和空间位阻的 α-取代肼酸残基的受限肽来证明。

  DOI：

  10.1021/ol5026684

文献信息

• Design, Synthesis, and Evaluation of Matrix Metalloprotease Inhibitors Bearing Cyclopropane-Derived Peptidomimetics as P1‘ and P2‘ Replacements
  作者：Andreas Reichelt、Christoph Gaul、Robin R. Frey、April Kennedy、Stephen F. Martin

  DOI：10.1021/jo0110698

  日期：2002.6.1

  hydrogen bonding capability associated with the P1'-P2' amide group. On the other hand, compounds 10 and 11, which contain a P2'-P3' retro amide group, were modest competitive inhibitors of a series of MMPs. The results obtained for 10 and 11 suggest that there may be a loss of hydrogen bonding capability associated with introducing the P2'-P3' retro amide group. However, because the conformationally constrained

  我们先前已经使用三取代的环丙烷作为肽替代物，以在许多重要酶的已知假肽抑制剂中诱导构象限制。环丙烷衍生的肽模拟物是新颖的，因为它们是少数以预定方式局部定向肽主链和氨基酸侧链的替代物。尽管已使用这些二肽等排体来模拟模仿chi（1）空间的gauche（-）构象的氨基酸侧链，但尚未评估它们将侧链投射为反方向的能力。作为朝着这个目标迈出的第一步，制备了构象受限的假肽8和10以及它们相应的柔性类似物9和11并作为基质金属蛋白酶（MMP）的抑制剂进行了测试。这些化合物是4和5的类似物 已知是有效的MMP抑制剂。相对于环丙烷上的肽主链取代基，预测8中的异丙基侧链和10中的芳环的反方向对应于5的P1'和P2'侧链与MMP结合时的已知方向。因此，明确设计了8和10，以探测MMP的S1'或S2'结合口袋的拓扑特征。他们还被设计来探索P1'-P2'酰胺基的重要性，该基团已知在几种MMP抑制剂复合物中形成高度保守的
• [EN] PYRIDINONE AND PYRIMIDINONE DERIVATIVES AS FACTOR XIA INHIBITORS<br/>[FR] DÉRIVÉS DE PYRIDINONE ET DE PYRIMIDINONE COMME INHIBITEURS DU FACTEUR XIA
  申请人：ONO PHARMACEUTICAL CO

  公开号：WO2013093484A1

  公开（公告）日：2013-06-27

  The present invention provides compounds of the general formula (I), their salts and N- oxides, and solvates and prodrugs thereof (wherein the characters are as defined in the description). The compounds of the general formula (I) are inhibitors of Factor XIa, so that they are useful in the prevention of and/or therapy for thromboembolic diseases.

  本发明提供了一般式(I)的化合物，它们的盐和N-氧化物，以及它们的溶剂合物和前药（其中字符如描述中所定义）。一般式(I)的化合物是因子XIa的抑制剂，因此它们在预防和/或治疗血栓栓塞疾病方面是有用的。
• Structure-Based Design, Synthesis, and Biological Evaluation of Irreversible Human Rhinovirus 3C Protease Inhibitors. 3. Structure−Activity Studies of Ketomethylene-Containing Peptidomimetics
  作者：Peter S. Dragovich、Thomas J. Prins、Ru Zhou、Shella A. Fuhrman、Amy K. Patick、David A. Matthews、Clifford E. Ford、James W. Meador、Rose Ann Ferre、Stephen T. Worland

  DOI：10.1021/jm980537b

  日期：1999.4.1

  rhinovirus (HRV) 3C protease (3CP) inhibitors are described. These compounds are comprised of a peptidomimetic binding determinant and an ethyl propenoate Michael acceptor moiety which forms an irreversible covalent adduct with the active site cysteine residue of the 3C enzyme. The ketomethylene-containing inhibitors typically display slightly reduced 3CP inhibition activity relative to the corresponding

  描述了各种含酮亚甲基的人鼻病毒（HRV）3C蛋白酶（3CP）抑制剂的基于结构的设计，化学合成和生物学评估。这些化合物由拟肽结合决定簇和丙酸乙酯迈克尔受体部分组成，其与3C酶的活性位点半胱氨酸残基形成不可逆的共价加合物。相对于相应的肽衍生的分子，含酮亚甲基的抑制剂通常显示出略微降低的3CP抑制活性，但它们也显示出显着改善的抗病毒特性。已显示对含酮亚甲基化合物的优化可提供几种高活性3C蛋白酶抑制剂，它们可作为有效的抗鼻病毒药物（EC90 = <1 microM），对抗细胞培养中的多种病毒血清型。
• A Stereocontrolled Synthesis of Monofluoro Ketomethylene Dipeptide Isosteres
  作者：Robert V. Hoffman、Junhua Tao

  DOI：10.1021/jo981334y

  日期：1999.1.1

  A simple, stereocontrolled synthesis of monofluoro ketomethylene dipeptide isosteres has been developed. N-Tritylated ketomethylene dipeptide isosteres, prepared from N-tritylated amino acids, are converted to their Z-TMS enol ethers and fluorinated with Selectfluor. There is cooperative stereocontrol between the N-tritylamine group and the alkyl group at C-2. The method is short (six steps), diastereoselective

  已经开发了简单的立体控制的单氟酮亚甲基二肽等排体的合成。由N-三苯甲基化的氨基酸制备的N-三苯甲基化的酮亚甲基二肽等位基因被转化为其Z-TMS烯醇醚并用Selectfluor进行氟化。N-三苯甲基胺基和C-2处的烷基之间存在协同立体控制。该方法很短（六个步骤），非对映选择性（85-> 95％）和对映选择性（> 95％）。
• A simple, stereoselective synthesis of ketomethylene dipeptide isosteres
  作者：Robert V. Hoffman、Junhua Tao

  DOI：10.1016/s0040-4020(97)00410-9

  日期：1997.5

  An exceedingly simple, general, and stereoselective method for the preparation of ketomethylene dipeptide isosteres (5-(carbobenzyloxyamino)-2-alkyl-γ-ketoesters) from Cbz-protected amino acids and scalemic 2-triflyloxy esters has been developed. The method is short (three steps), efficient, and highly diastereoselective and enantioselective.

  已经开发了一种非常简单，通用和立体选择性的方法，该方法可从Cbz保护的氨基酸和规模的2-triflyloxy酯制备酮亚甲基二肽等位异构体（5-（羰基苄氧基氨基）-2-烷基-γ-酮酸酯）。该方法是短的（三个步骤），有效的，高度非对映选择性和对映选择性的。