Diisopropyl (R)-glutamate | 115963-19-4

• 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: Diisopropyl (R)-glutamate
• 英文别名: D-diisopropyl glutamate；dipropan-2-yl (2R)-2-aminopentanedioate
• CAS: 115963-19-4
• 化学式: C₁₁H₂₁NO₄
• 分子量: 231.292
• InChiKey: MULMBFBZGGMART-SECBINFHSA-N

物化性质

• 沸点：
  115-117 °C(Press: 0.15 Torr)
• 密度：
  1.023 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  78.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Diisopropyl (R)-glutamate 、 三氟乙酸酐 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 dipropan-2-yl (2R)-2-[(2,2,2-trifluoroacetyl)amino]pentanedioate
  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
• 作为产物：
  描述：

  D-谷氨酸 、 异丙醇 在 乙酰氯 作用下， 反应 1.0h， 生成 Diisopropyl (R)-glutamate
  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

• Stereospecific Synthesis of 2,3-Dimethoxy-naphtho[1,2-b]indolizidine
  作者：Gwan Sun Lee、Yong Seo Cho、Sang Chul Shim、Wan Joo Kim、Ernst Eibler、Wolfgang Wiegrebe

  DOI：10.1002/ardp.19893221008

  日期：——

  (11aR)‐2,3‐dimethoxy‐naphtho[1,2‐b]indolizidine (9a and 9b) were synthesized from optically pure L‐ and D‐glutamic acid through several steps (scheme 1). All the intermediates of the route to the optical antipodes of 9 exhibit identical physical and spectral properties except the sign of the optical rotation values. The optical purity of the enantiomers of 6 was checked by 1H‐NMR spectra using Eu(tfc)3,

  (11aS) - 和 (11aR) -2,3 - 二甲氧基 - 萘并 [1,2 - b] 吲哚里西啶（9a 和 9b）由光学纯的 L- 和 D-谷氨酸通过几个步骤合成（方案 1）。除了旋光度值的符号外，通往 9 的光学对映体的路线的所有中间体都表现出相同的物理和光谱特性。6 对映异构体的光学纯度通过使用 Eu (tfc) 3 的 1H-NMR 光谱检查，9 的对映异构体通过手性柱上的 HPLC 分离；9a 和 9b 的外消旋量分别小于 3%。
• Asymmetric synthesis of phenanthroindolizidine alkaloids with hydroxyl group at the C14 position and evaluation of their antitumor activities
  作者：Takashi Ikeda、Takashi Yaegashi、Takeshi Matsuzaki、Syusuke Hashimoto、Seigo Sawada

  DOI：10.1016/j.bmcl.2010.11.008

  日期：2011.1

  The asymmetric total synthesis of the strongly cytotoxic phenanthroindolizidine alkaloid 3 was achieved. Using the same route, various derivatives were also synthesized. Cytotoxicity of those synthetic compounds was evaluated and compounds 19, 23, and 27 demonstrated potent cytotoxicities similar to that of 3. The in vivo antitumor efficacy of selected compounds was also evaluated and 23 demonstrated moderate antitumor efficacy. (C) 2010 Elsevier Ltd. All rights reserved.
• LEE, GWAN SUN;CHO, YONG SEO;SHIM, SANG CHUL;KIM, WAN JOO;EIBLER, EMST;WIE+, ARCH. PHARM., 322,(1989) N0, C. 607-611
  作者：LEE, GWAN SUN、CHO, YONG SEO、SHIM, SANG CHUL、KIM, WAN JOO、EIBLER, EMST、WIE+

  DOI：——

  日期：——
• Stable carbon isotope analysis of amino acid enantiomers by conventional isotope ratio mass spectrometry and combined gas chromatography/isotope ratio mass spectrometry
  作者：J. A. Silfer、M. H. Engel、S. A. Macko、E. J. Jumeau

  DOI：10.1021/ac00004a014

  日期：1991.2.15

  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.