谷氨酸二甲酯 | 6525-53-7

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: 谷氨酸二甲酯
• 英文名称: L-glutamic acid dimethyl ester
• 英文别名: H-Glu(OMe)-OMe；dimethyl L-glutamate；(S)-dimethyl 2-aminopentanedioate；dimethyl (2S)-2-aminopentanedioate
• CAS: 6525-53-7
• 化学式: C₇H₁₃NO₄
• mdl: MFCD08669750
• 分子量: 175.185
• InChiKey: YEJSPQZHMWGIGP-YFKPBYRVSA-N

物化性质

• 熔点：
  136-138 °C(Solv: ligroine (8032-32-4))
• 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

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  -20°C密封保存，干燥、避光且在惰性气体环境中。

制备方法与用途

谷氨酸二甲酯是谷氨酸的膜渗透类似物，可刺激葡萄糖诱导的胰岛素释放。它能抑制KATP通道活性，并且能够抑制纤细杆菌生长，导致细胞分裂异常。因此，谷氨酸二甲酯可用于糖尿病、葡萄糖转运、磷酸化和进一步代谢的研究[1][2][3][4]。

反应信息

• 作为反应物：
  描述：

  谷氨酸二甲酯 在 sodium tetrahydroborate 、 magnesium sulfate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 Methanesulfonic acid (S)-1-(4-methoxy-benzyl)-5-oxo-pyrrolidin-2-ylmethyl ester
  参考文献：
  名称：

  N-（4-甲氧基苄基）-2-吡咯烷酮氧化为N-（4-甲氧基苯甲酰基）-2-吡咯烷酮。快速进入旋光阿尼西坦类似物

  摘要：

  容易获得的N-（4-甲氧基苄基）-5-烷基吡咯烷酮-2-酮被氧化为相应的N-（4-甲氧基苯甲酰基）-5-烷基吡咯烷酮-2-酮可直接获得对映体纯的认知的5-烷基类似物活化剂阿尼西坦。

  DOI：

  10.1016/0040-4020(96)00732-6
• 作为产物：
  描述：

  metatacarboline B 在 盐酸 、 水 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 1.17h， 生成 谷氨酸二甲酯
  参考文献：
  名称：

  HR-MALDI-MS Imaging Assisted Screening of β-Carboline Alkaloids Discovered from Mycena metata

  摘要：

  Fruiting bodies of Mycena metata were screened for the presence of new secondary metabolites by means of HPLC-UV, LC-HR-ESIMS, and high-resolution matrix-assisted laser desorption/ionization mass spectrometry imaging (HR-MALDI-MS imaging). Thus, a new beta-carboline alkaloid, 6-hydroxymetatacarboline D (1d), was isolated from fruiting bodies of M. metata. 6-Hydroxymetatacarboline D consists of a highly substituted beta-carboline skeleton, which is likely to be derived biosynthetically from L-tryptophan, 2-oxoglutaric acid, L-threonine, and L-proline. The structure of the alkaloid was established by 2D NMR spectroscopic methods and HR-ESIMS. Moreover, by extensive application of LC-HR-ESIMS, LC-HR-ESIMS/MS, and LC-HR-ESIMS3 techniques we were able to elucidate the structures of a number of accompanying beta-carboline alkaloids, 1a-1c, 1e-1i, and 2a-2g, structurally closely related to 6-hydroxymetatacarboline D, which are present in M. metata in minor amounts. The absolute configuration of the stereogenic centers of the beta-carboline alkaloids was determined by GC-MS comparison with authentic synthetic samples after hydrolytic cleavage and derivatization of the resulting amino acids.

  DOI：

  10.1021/np300455a
• 作为试剂：
  描述：

  、 L-天门冬氨酸 、 L-正亮氨酸 、 (R)-2-氨基庚酸 、 (R)-2-氨基辛酸 、 DL-2-氨基辛酸 在 methyl ester 、 谷氨酸二甲酯 作用下， 以the methyl ester of (S)-glutamine in place of (S)-glutamic acid dimethyl ester, there were obtained 2-[4-(2(R)-carboxypyrrolidine-1-sulfonyl)benzoylamino]butane-(S)-dioic acid, MS的产率得到L-谷氨酰胺
  参考文献：
  名称：

  US06143776

  摘要：

  公开号：

文献信息

• Novel Dipeptides incorporating selenoamino acids with enhanced bioavailability- Synthesis, pharmaceutical and cosmeceutical applications thereof
  申请人：Majeed Muhammed

  公开号：US20080026017A1

  公开（公告）日：2008-01-31

  Disclosed is a novel synthetic method for isomeric peptides through an appropriate linkage of L-selenomethionine or Se-Methyl-L-selenocysteine with L-glutamic acid. The novel synthetic method produces isomeric peptides of L-selenomethionine or Se-Methyl-L-selenocysteine that exhibit (i) enhanced water solubility; (ii) enhanced rate of dissolution in water; (iii) enhanced bioavailability; (iv) excellent vascular endothelial growth factor promoting activity; (v) excellent anti-5-alpha-reductase activity; (vi) capabilities to prevent/reduce “hair fall” and promote “hair growth”, thereby maintaining a perfect homeostasis for “hair care”. Cosmeceutical and pharmaceutical compositions comprising the isomeric peptides obtained through an appropriate linkage of L-selenomethionine or Se-Methyl-L-selenocysteine with L-glutamic acid are also disclosed. Other dipeptides with several other amino acids and uses thereof are also disclosed.

  揭示了一种新颖的合成方法，通过将L-硒代蛋氨酸或Se-甲基-L-硒蛋氨酸与L-谷氨酸适当连接，制备L-硒代蛋氨酸或Se-甲基-L-硒蛋氨酸的同分异构肽。这种新颖的合成方法产生的同分异构肽具有以下特点：(i)增强的水溶性；(ii)在水中溶解速度增强；(iii)增强的生物利用度；(iv)出色的血管内皮生长因子促进活性；(v)出色的抗5α-还原酶活性；(vi)具有预防/减少“脱发”和促进“头发生长”的能力，从而维持“头发护理”的完美稳态。还揭示了包括通过将L-硒代蛋氨酸或Se-甲基-L-硒蛋氨酸与L-谷氨酸适当连接获得的同分异构肽的化妆品和药用组合物。还揭示了包括其他多种氨基酸的二肽及其用途。
• SUBSTITUTED BRIDGED UREA ANALOGS AS SIRTUIN MODULATORS
  申请人：GLAXOSMITHKLINE LLC

  公开号：US20150152108A1

  公开（公告）日：2015-06-04

  The present invention relates to novel substituted bridged urea compounds, corresponding related analogs, pharmaceutical compositions and methods of use thereof. Sirtuin-modulating compounds of the present invention may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders, which include, but are not limited to, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. The present invention also related to compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

  本发明涉及新型取代桥式脲化合物，相应的相关类似物，药物组合物以及其使用方法。本发明的抑制素调节化合物可用于延长细胞寿命，并治疗和/或预防各种疾病和疾病，包括但不限于与衰老或压力、糖尿病、肥胖、神经退行性疾病、心血管疾病、血液凝块疾病、炎症、癌症和/或潮红有关的疾病或疾病，以及那些会受益于增加线粒体活性的疾病或疾病。本发明还涉及包含抑制素调节化合物与另一治疗剂组合的组合物。
• Synthesis of individual glutamate-containing phosphonamidothionate stereoisomers
  作者：Haiyan Lu、Ying Hu、Cindy J Choy、Jeremy P Mallari、Alina F Villanueva、Annamarie F Arrozal、Clifford E Berkman

  DOI：10.1016/s0040-4039(01)00746-8

  日期：2001.6

  acquisition of the individual stereoisomers of chiral phosphonothioic acids is anticipated to reveal the significance of phosphorus stereochemistry upon the inhibition of metallocarboxypeptidases as well as their utility as chiral and stereoselective inhibitory probes. Two methods for preparing individual glutamate-containing phosphonamidothioic acid diastereomers have been identified. One method achieves the

  预期获得手性膦酸硫代磷酸的各个立体异构体将揭示磷立体化学在抑制金属羧肽酶及其作为手性和立体选择性抑制探针的实用性方面的重要性。已经鉴定了两种制备单独的含谷氨酸的磷酸氨基硫代酸非对映异构体的方法。一种方法是通过中间体9-芴甲氧基膦酰胺酸酯的分步结晶来实现拆分的，而第二种方法是通过中间体β-（酰基巯基）乙基膦酰胺基硫代酸酯的色谱拆分来实现的。
• 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。