D-谷氨酸,二甲基酯 | 16422-27-8

• 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
• 中文名称: D-谷氨酸,二甲基酯
• 英文名称: D-glutamic acid dimethyl ester
• 英文别名: dimethyl D-glutamate；1,5-dimethyl (2R)-2-aminopentanedioate；dimethyl L-glutamate；(R)-dimethyl 2-aminopentanedioate；dimethyl (2R)-2-aminopentanedioate
• CAS: 16422-27-8
• 化学式: C₇H₁₃NO₄
• mdl: MFCD15147183
• 分子量: 175.185
• InChiKey: YEJSPQZHMWGIGP-RXMQYKEDSA-N

物化性质

• 沸点：
  224.3±25.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.714
• 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：

  D-谷氨酸,二甲基酯 在 盐酸 、 methyloxirane 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 D-谷氨酸
  参考文献：
  名称：

  Schollkopf; Pettig; Busse, Synthesis, 1986, vol. NO. 9, # 9, p. 737 - 740

  摘要：

  DOI：
• 作为产物：
  描述：

  benzyloxycarbonylglutamic acid dimethyl ester 在 10percent Pd/C 氢气 作用下， 以 甲醇 为溶剂， 生成 D-谷氨酸,二甲基酯
  参考文献：
  名称：

  Synthesis of Muramyl Peptides Containing meso-Diaminopimelic Acid

  摘要：

  Chain-extension Of L-glutamate aldehyde 3 by means of the Wittig-Homer reaction furnished the desired C-7 dicarboxylic acid derivative, which in turn, after C-C double bond hydrogenation and protecting group manipulation, afforded the 2,6-diaminopimelic acid derivatives (S,R)-9 and (S,S)-9, both with the desired orthogonal protecting group pattern. Synthesis of the muramic acid derivative 15 and attachment of an L-alanine residue furnished muramyl-L-alanine 18. The corresponding 1,6-anhydromuramic acid derivative 26 was obtained similarly. Treatment of these compounds with peptides 28-30 and with the 2,6-diaminopimelic acid containing di- and tripeptides 32a, 32b, and 35 gave the protected muramyl peptides 17, 37, 40, 42, 44, 46, and 49a and 49b, which, after deprotection, afforded the desired target molecules muramyl-L-alanine (38), muramyl-L-alanyl-D-glutamic acid (39), muramyl-L-alanyl-D-glutaminide (41), muramyl-L-alanyl-D-isoglutaminyl-L-lysine (43), muramyl-L-alanyl-D-isoglutaminyl-(2S,6R)-2,6-diaminopimelic acid (45), muramyl-L-alanylL-isoglutaminyl-(2S,6R)-2,6-dian-Anopimelinyl-D-alanine (47), 1,6-anhydromuramyl-L-alanyl-D-isoglutaminyl-(2S,6R)-2,6-diaminopimelic acid (50a), and 1,6-anhydromuramyl-L-alanyl-Disoglutaminyl-(2S,6S)-2,6-diaminiopimelic acid (50b). (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200208)2002:16<2710::aid-ejoc2710>3.0.co;2-8

文献信息

• Stereoselective inhibition of glutamate carboxypeptidase by organophosphorus derivatives of glutamic acid
  作者：Jeremy P. Mallari、Cindy J. Choy、Ying Hu、Alicia R. Martinez、Mia Hosaka、Yoko Toriyabe、Jack Maung、Joseph E. Blecha、Stephen F. Pavkovic、Clifford E. Berkman

  DOI：10.1016/j.bmc.2004.08.016

  日期：2004.11

  stereoselective inhibition consistent with the configuration of the chiral phosphorus center, this effect was generally not remarkable. More important, was the effect of carbon stereochemistry upon glutamate carboxypeptidase inhibition as exemplified by a limited series of enantiomeric pairs of phosphonamidate and phosphonamidodithionate derivatives of glutamic acid. The phosphonamidate analogs derived

  制备一系列（S）-和（R）-谷氨酸的烷基和芳基膦酰基，硫代膦酰基和二硫代膦酰基衍生物，并检查其对谷氨酸羧肽酶（羧肽酶G）的抑制能力。磷酸亚氨基二硫代酸和单个磷酸氨基硫代酸非对映异构体的获得是通过常见的氨基磷酸硫代氨基甲酸酯前体实现的，该前体也允许对磷酸氨基硫代酸的手性磷中心进行色谱拆分。该系列中最有效的抑制剂是谷氨酸天然异构体的正丁基膦酰胺酸酯衍生物。尽管每对非对映异构体对三个磷酸氨基硫代酸酯都显示出与手性磷中心的构型一致的立体选择性抑制，但这种效果通常并不明显。更重要的是，碳立体化学对谷氨酸羧肽酶抑制的影响，如谷氨酸的膦酰胺和膦酰胺二硫代酸酯衍生物的一系列对映异构体对所例示的。与它们的对映异构体相反，衍生自谷氨酸的非天然立体异构体的膦酰胺类似物没有抑制效力。令人惊讶地，衍生自谷氨酸的非天然立体异构体的磷酸氨基二硫代磷酸酯显示出比其天然来源的对映体更大的抑制效力。与它们的对映异构体相反，衍
• New Chiral Derivatizing Agents: Convenient Determination of Absolute Configurations of Free Amino Acids by ¹H NMR
  作者：Michio Kurosu、Kai Li

  DOI：10.1021/ol8028719

  日期：2009.2.19

  The chiral carbonate reagents 5 allow for the direct and unambiguous determination of the absolute configurations of a wide range of free amino acids using 1H NMR. By using a ∼3:1 mixture of (S)-5 and (R)-5, absolute configurations of the corresponding carbamates are determined by only analyzing the nitrogen protons.

  手性碳酸酯试剂5允许使用1 H NMR直接和明确地确定各种游离氨基酸的绝对构型。通过使用〜（S）-5和（R）-5的〜3：1混合物，仅通过分析氮质子即可确定相应氨基甲酸酯的绝对构型。
• A Recyclable Organocatalyst for Asymmetric Michael Addition
  作者：Mei Yang、Yuecheng Zhang、Jiquan Zhao、Qiusheng Yang、Yi Ma、Xiaohui Cao

  DOI：10.1007/s10562-016-1693-x

  日期：2016.3

  In this study, a new organocatalyst derived from proline was developed and shown to be an efficient catalyst for asymmetric Michael addition reactions of ketones and aldehydes to nitroolefins with high diastereo- and enantioselectivities. (syn;anti up to 99:1, ee. up to 98 %.). Furthermore, the catalyst is easily recovered and could be reused six times without significant loss of its ability to affect

  在这项研究中，开发了一种衍生自脯氨酸的新型有机催化剂，它是酮和醛与硝基烯烃的不对称迈克尔加成反应的有效催化剂，具有高非对映选择性和对映选择性。（syn;anti 高达 99:1，ee。高达 98%。）。此外，催化剂很容易回收，可以重复使用六次，而不会显着丧失其影响不对称反应结果的能力。此外，对模型反应进行了 B3LYP/6-311G(d,p)//6-311 + G(2dp,f) 水平的计算研究，并证实了以下假设：首先，羧基之间的氢键基团和硝基在催化中起重要作用，其次是酮反应形成2S的重新攻击的能垒，3R 产物低于导致 2S、3R 产物的 si-face 攻击。Graphical Abstract 使用先前报道的有机催化剂（图中的铅化合物）的结构改性设计了一种高效且可回收的有机催化剂，用于不对称迈克尔加成。引入的羧基不仅提高了对映选择性，而且为催化剂的回收带来了便利。
• Chemical synthesis and adjuvant activity of N-acetylmuramyl-L-alanyl-D-isoglutamine (MDP) analogs.
  作者：KEIICHI KAMISANGO、IKUO SAIKI、YOSHIRO TANIO、SHIGERU KOBAYASHI、TSUNEHIKO FUKUDA、ISAO SEKIKAWA、ICHIRO AZUMA、YUICHI YAMAMURA

  DOI：10.1248/cpb.29.1644

  日期：——

  Twenty-two kinds of N-acetylmuramyl-L-alanyl-D-isoglutamine (MDP) analogs were synthesized and their adjuvant activity on the induction of delayed-type hypersensitivity to ABA-N-acetyl-L-tyrosine was examined. The L-alanine residue of MDP could be replaced with certain other amino acid residues without loss of activity. The structureactivity relationship of these compounds is discussed. With respect to replacement of the L-alanine residue of MDP in connection with adjuvant activity, it was shown that (1) amino acids having a suitable side chain were effective, (2) basic amino acids were unfavorable, (3) aromatic amino acids were unfavorable, and (4) acidic amino acids were effective. The D-isoglutamine residue of MDP was considered to be essential for the adjuvant activity. The adjuvant activity was decreased by esterification with methanol of the D-glutamic acid residue of MDP and related N-acetylmuramyldipeptides, but the adjuvant activity of D-glutamic acid diamide analogs was similar to that of MDP and its analogs.

  合成了二十二种N-乙酰胞壁酰-L-丙氨酰-D-异谷氨酰胺(MDP)的类似物,并检验了它们对诱导对ABA＿N-乙酰-L-酪氨酸的迟发型过敏反应的佐剂活性。MDP的L-丙氨酸残基能为某些其他氨基酸残基所置换,而活性不变。讨论了这些化合物的结构-活性关系。关于MDP中L-丙氨酸残基的置换和佐剂活性,表明; (1)具有合适侧链的氨基酸是有效的; (2)碱性氨基酸不是有利的; (3)芳香族的氨基酸不是有利的; (4)酸性氨基酸是有效的。认为MDP的D-异谷氨酰胺残基对佐剂活性是必要的。与MDP和有关N-乙酰胞壁酰二肽的D-谷氨酸残基的酯化作用使佐剂活性降低,但D-谷氨酸二酰胺类似物的佐剂活性与MDP及其类似物的佐剂活性相似。
• Hydantoin-Free Synthesis of Peptide Ester Isocyanates, Isothiocyanates, and Dipeptidyl Ureas: The Application of Zinc Dust in a Carbonylation Procedure without Base
  作者：Vommina Sureshbabu、N. Narendra、T. Vishwanatha

  DOI：10.1055/s-0030-1260216

  日期：2011.10

  Non-Schotten-Baumann conditions are described for the hydantoin-free synthesis of peptide ester isocyanates using activated zinc dust as a non-basic HCl scavenger. Also, the procedure gives no N-acylated products in the case of the conversion of amino acid and peptide amides into isocyanates.

  在使用活性锌粉作为非碱性HCl清除剂的情况下，描述了无需使用海因（hydantoin）的肽酯异氰酸酯自由合成方法，即非Schotten-Baumann条件。此外，在将氨基酸和肽酰胺转化为异氰酸酯的过程中，该方法不会产生N-酰化产物。