(S)-4-Methyl-2-(2,2,2-trifluoro-acetylamino)-pentanoic acid isopropyl ester | 53375-35-2

• 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: (S)-4-Methyl-2-(2,2,2-trifluoro-acetylamino)-pentanoic acid isopropyl ester
• 英文别名: propan-2-yl (2S)-4-methyl-2-[(2,2,2-trifluoroacetyl)amino]pentanoate
• CAS: 53375-35-2
• 化学式: C₁₁H₁₈F₃NO₃
• 分子量: 269.264
• InChiKey: MGXDWBLMYIJEEM-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  L-亮氨酸 在 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 1.17h， 生成 (S)-4-Methyl-2-(2,2,2-trifluoro-acetylamino)-pentanoic acid isopropyl ester
  参考文献：
  名称：

  Stable carbon isotope analysis of amino acid enantiomers by conventional isotope ratio mass spectrometry and combined gas chromatography/isotope ratio mass spectrometry

  摘要：

  The application of a combined gas chromatography/isotope ratio mass spectrometry (GC/IRMS) method for stable carbon isotope analysis of amino acid enantiomers is presented. This method eliminates the numerous preparative steps integral to the isolation of amino acids and amino acid enantiomers from protein hydrolyzates that precede delta-C-13 analysis by conventional isotope ratio mass spectrometry. Unlike hydrocarbons, amino acids require derivatization prior to GC/IRMS analysis. Replicate delta-C-13 analyses of trifluoroacetyl (TFA) isopropyl ester derivatives of 22 amino acids by IRMS revealed that the derivatization process is reproducible, with an average error (1 standard deviation) of 0.10% +/- 0.09%. The average analytical error for analysis of amino acid derivatives by GC/IRMS was 0.26% +/- 0.09%. In general, absolute differences between IRMS and GC/IRMS analyses were less than 0.5%. The derivatization process introduces a distinct, reproducible isotopic fractionation that is constant for each amino acid type. The observed fractionations preclude direct calculation of underivatized amino acid delta-C-13 values from their respective TFA isopropyl ester delta-C-13 compositions through mass balance relationships. Derivatization of amino acid standards of known stable carbon isotope compositions in conjunction with natural samples, however, permits computation of the original, underivatized amino acid delta-C-13 values through use of an empirical correction for the carbon introduced during the derivatization process.

  DOI：

  10.1021/ac00004a014

文献信息

• Nucleophilic Substitution Reactions of Alkyl Halides by Using New Polymer-Supported Reagents Containing Hemin
  作者：Kiyoshi Saito、Kaoru Harada

  DOI：10.1246/bcsj.62.2562

  日期：1989.8

  hemin, divinylbenzene, and 2-methyl-5-vinylpyridine was synthesized by suspension copolymerization. Substitution reactions of primary, secondary, and tertiary alkyl halides with the hemin copolymer combined with cyanide, azide, and thiocyanate ions were given satisfactory yields. This reaction mechanism was revealed to be a SNi type on the basis of stereochemical study. The hemin copolymer was not only

  通过悬浮共聚反应合成了一种由氯化血红素、二乙烯基苯和2-甲基-5-乙烯基吡啶组成的新型高分子试剂。伯、仲和叔烷基卤与氯化血红素共聚物与氰化物、叠氮化物和硫氰酸根离子的取代反应得到了令人满意的产率。根据立体化学研究，该反应机理被揭示为 SNi 型。氯化血红素共聚物不仅是具有功能性的聚合物负载试剂，而且还用于将产物与反应混合物分离。
• Metal-Organic Framework Co(<scp>D</scp>-Cam)_1/2(bdc)_1/2(tmdpy) for Improved Enantioseparations on a Chiral Cyclodextrin Stationary Phase in Gas Chromatography
  作者：Hong Liu、Sheng-Ming Xie、Ping Ai、Jun-Hui Zhang、Mei Zhang、Li-Ming Yuan

  DOI：10.1002/cplu.201402067

  日期：2014.8

  peramylated β‐cyclodextrin+MOF shows excellent selectivity for the recognition of racemates, and higher resolutions are achieved on the peramylated β‐cyclodextrin+MOF stationary phase. Experimental results indicate that the use of Co(D‐Cam)1/2(bdc)1/2(tmdpy) can improve enantioseparations on peramylated β‐cyclodextrins. This is the first report that chiral MOFs can improve enantioseparations on a chiral stationary

  初步努力结合手性金属-有机构架（MOF），钴（d -Cam）1/2（BDC）1/2（tmdpy）（d -Cam = d樟脑酸，BDC = 1,4-苯二甲酸，tmdpy = 4,4'-三亚甲基二吡啶），用过酰胺化的β-环糊精来研究MOF的使用是否可以增强对环糊精固定相的对映体分离。与掺入含有氯化钠的MOF中的高酰化β-环糊精色谱柱相比，高酰化β-环糊精+ MOF色谱柱对外消旋体的识别具有出色的选择性，并且在高酰化的β-环糊精+ MOF固定相上实现了更高的分离度。实验结果表明，Co（D‐Cam）1/2（bdc ）1/2（tmdpy）可以改善对氨基甲酸酯化的β-环糊精的对映体分离。这是第一个报道，手性MOF可以改善手性固定相上的对映体分离，用于色谱分离。
• Chiral 3D Open-Framework Material Ni(D-cam)(H₂O)₂Used as GC Stationary Phase
  作者：Shengming Xie、Bangjin Wang、Xinhuan Zhang、Junhui Zhang、Mei Zhang、Liming Yuan

  DOI：10.1002/chir.22260

  日期：2014.1

  explored for analytical applications because of their outstanding properties such as high surface areas, flexibility and specific structure features, especially for chromatography application in recent years. In this work, a chiral MOF Ni(D‐cam)(H2O)2 with unusual integration of molecular chirality, absolute helicity, and 3‐D intrinsic chiral net was chosen as stationary phase to prepare Ni(D‐cam)(H2O)2‐coated

  由于金属有机骨架（MOF）具有出色的特性，例如高表面积，柔韧性和特殊的结构特征，因此已经在分析应用中进行了探索，尤其是在近年来的色谱应用中。在这项工作中，选择具有手性，分子绝对性和3D固有手性网络异常整合的手性MOF Ni（D-cam）（H 2 O）2作为固定相来制备Ni（D-cam） H 2 O）2带涂层的开放式管柱，用于高分辨率气相色谱（GC）分离。通过动态涂覆法制备了两种具有不同内径和长度的熔融石英空心管柱，包括A柱（内径30 m×250 µm）和B柱（内径2 m×75 µm）。使用正十二烷作为分析物在120°C下对两根色谱柱的色谱性能进行了研究。两个金属-有机骨架（MOF）柱的理论塔板数（板/米）分别为1300和2750。外消旋体，异构体和直链烷烃混合物用作分析物以评估Ni（D-cam）（H 2 O）2的分离性能涂层开放管柱。结果表明，该色谱柱能够很好地分离异构体和直链烷烃混合物，
• Structure, chemistry, and biological activity of pseudophomins A and B, new cyclic lipodepsipeptides isolated from the biocontrol bacterium Pseudomonas fluorescens
  作者：M.Soledade C Pedras、Nargis Ismail、J.Wilson Quail、Susan M Boyetchko

  DOI：10.1016/s0031-9422(02)00617-9

  日期：2003.4

  configuration of the amino acid residue Leu-1, due to gamma-lactam formation followed by selective cleavage of the adjacent N(8)-C(7) bond. To the best of our knowledge this is the first application of gamma-lactam formation to the determination of absolute configuration of an adjacent amino acid. Pseudophomin B showed higher antifungal activity against the phytopathogens Phoma lingam/Leptosphaeria maculans

  假单胞菌素 A 和 B 是从荧光假单胞菌 BRG100 菌株中分离的环状脂缩肽，BRG100 是一种具有生物防治植物病原体和杂草的潜在应用的细菌。它们的化学结构是通过光谱数据、X 射线晶体学和选择性化学降解的组合建立的。这种独特的化学降解允许明确确定氨基酸残基 Leu-1 的绝对配置，这是由于形成 γ-内酰胺，然后选择性裂解相邻的 N(8)-C(7) 键。据我们所知，这是首次将 γ-内酰胺形成应用于确定相邻氨基酸的绝对构型。Pseudophhomin B 对植物病原体 Phoma lingam/Leptosphaeria maculans 和核盘菌的抗真菌活性高于假单胞菌 A，并且可能是 BRG100 菌株 EtOAc 提取物抗真菌活性的主要成分。相比之下，与pseudophhomin B相比，pseudophhomin A对绿狗尾草（狗尾草）根萌发的抑制作用更强。
• 3D-structure of cycloreticulin C and glabrin A, cyclopeptides from the seeds of Annona reticulata
  作者：Alassane Wélé、Claudine Mayer、Dermigny Quentin、Yanjun Zhang、Alain Blond、Bernard Bodo

  DOI：10.1016/j.tet.2008.10.055

  日期：2009.1

  Two cyclopeptides, the cycloheptapeptide cycloreticulin C, cyclo(Pro(1)-Gly(2)-Gln(3)-Pro(4)-Pro(5)-Tyr(6)-Val(7)) (1), and the cyclohexapeptide glabrin A, cyclo(Pro(1)-Gly(2)-Leu(3)-Val(4)-Ile(5)-Tyr(6)) (2), have been isolated from the methanol extract of the seeds of Annona reticulata. Their Structures were elucidated on the basis of the MS/MS fragmentation using a Q-TOF mass spectrometer equipped with an ESI Source, chemical degradation and extensive 2D-NMR. The solution conformation of cycloreticulin C involves two beta-turns, one of type II with trans-Pro(1) and Gly(2) at the corners, another of type VIa with trans-Pro(4) and cis-Pro(5) at the corners, and followed by a beta-bulge at the Tyr(6)-Val(7) level. The solid state and solution conformations of glabrin A have been analyzed by X-ray and 2D-NMR studies, respectively, and are characterized by the presence of two beta-turns, the first of type VIa and the second intermediary between types I and III at the solid state and a gamma-turn in solution. (C) 2008 Elsevier Ltd. All rights reserved.