(2S)-4-methylglutamic acid | 2596-04-5

• 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: (2S)-4-methylglutamic acid
• 英文别名: 4-methylglutamate；(2S,4Ξ)-2-amino-4-methyl-glutaric acid；(2S,4Ξ)-2-Amino-4-methyl-glutarsaeure；gamma-methyl glutamic acid；γ-Methyl-L-glutaminsaeure；γ-Methylglutaminsaeure；4-Methyl-L-glutamate；(2S)-2-amino-4-methylpentanedioic acid
• CAS: 2596-04-5
• 化学式: C₆H₁₁NO₄
• 分子量: 161.158
• InChiKey: KRKRAOXTGDJWNI-BKLSDQPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-4-methylglutamic acid 在 硫酸 、 sodium nitrite 作用下， 反应 12.0h， 以74%的产率得到(2S,4S)-(-)-cis-4-methyl-tetrahydro-5-oxo-2-furancarboxylic acid
  参考文献：
  名称：

  Nishida, Yoshihiro; Ohrui, Hiroshi; Meguro, Hiroshi, Agricultural and Biological Chemistry, 1984, vol. 48, # 5, p. 1211 - 1216

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲基-2-酮戊二酸 在 bovine glutamic dehydrogenase 1,4-dihydronicotinamide adenine dinucleotide 、 L-谷氨酸 作用下， 以 phosphate buffer 为溶剂， 生成 (2S)-4-methylglutamic acid
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Glutamic Acid Analogues:  Substrate Specificity and Synthetic Applications of Branched Chain Aminotransferase from Escherichia coli

  摘要：

  [GRAPHICS]A new route to alpha-keto acids is described, based on the ozonolysis of enol acetates obtained from alpha-substituted beta-keto esters. Escherichia coli branched chain aminotransferase (BCAT) activity toward a variety of substituted 2-oxoglutaric acids was demonstrated analytically. BCAT was shown to have a broad substrate spectrum, complementary to that of aspartate aminotransferase, and to offer access to a variety of glutamic acid analogues. The usefulness of BCAT was demonstrated through the synthesis of several 3- and 4-substituted derivatives.

  DOI：

  10.1021/jo070805q
• 作为试剂：
  描述：

  (+/-)-(2S,4R)-4-methylglutamic acid 、 钠 、 硫磺 、 乙酰氨基丙二酸二乙酯 、 甲基丙烯酸甲酯 在 乙醇 、 盐酸 、 水 、 三辛胺 、 氯仿 、 丙酮 、 (2S)-4-methylglutamic acid 作用下， 以 乙醇 、 水 为溶剂， 以(2R,4S) and (2S,4R)-4-methyl glutamic acid was obtained by fractional crystallization in water的产率得到(2S,4R)-4-methylglutamic acid
  参考文献：
  名称：

  Screen for glutamate reuptake inhibitors, stimulators, and modulators

  摘要：

  本文揭示了一种识别结合或调节谷氨酸转运体的化合物的方法。揭示的方法用于识别可以抑制、刺激或调节谷氨酸转运体活性的化合物，从而影响谷氨酸的再摄取。该方法是一种筛选技术，其中已知与谷氨酸受体结合的化合物（例如，谷氨酸受体配体，包括许多激动剂和拮抗剂）与谷氨酸转运体结合，并筛选化合物以识别可以改变谷氨酸受体结合化合物的结合的化合物。在揭示的测定中，被证明可以改变受体化合物从谷氨酸转运体中结合的化合物可以对谷氨酸转运体活性产生各种效应，包括激活或抑制。这些化合物预计会影响或干扰谷氨酸转运体的谷氨酸再摄取，从而可以用于调节、刺激或抑制谷氨酸再摄取。这些化合物对于治疗涉及谷氨酸转运体和谷氨酸受体激活的各种神经疾病和病症非常有用。其中一种化合物是（2S，4R）-4-甲基谷氨酸或[3H] -（2S，4R）-4-甲基谷氨酸。例如，过多的细胞外谷氨酸是谷氨酸受体过度激活的原因。通过刺激谷氨酸转运体的谷氨酸再摄取，可以通过降低细胞外谷氨酸浓度来缓解谷氨酸受体的过度激活。药物使用时，转运体化合物的前药形式更受欢迎。

  公开号：

  US20020115688A1

文献信息

• Ether and amide compounds and preparation of thereof as antidiadetics.
  申请人：——

  公开号：US20010008898A1

  公开（公告）日：2001-07-19

  Ether and amide derivatives are disclosed, which are represented by the following formula (I) and its pharmaceutical acceptable salt, and which are useful for the treatment of diabetes. 1 (with the provisos that (i) when A is —O—, then n is 2 or 3 (ii) when A is 2 then n is 1 or 2. R 3 is OH—, CH 3 SO 2 NH—, CF 3 SO 2 NH—, CH 3 SO 2 NHCH 2 —, CF 3 SO 2 NHCH 2 —, HOOC—, CH 3 OOC—, 3 HOOC—CH 2 SO 2 NH—, CF 3 —CH 2 SO 2 NH—, 4 R 8 —NHSO 2 —, R 8 —NHSO 2 —CH 2 —, HOOC—CH 2 —O—, HSO 3 N═CH—, or R 9 —SO 2 NHCO—; R 4 is H, OH, O-alkyl or O—CH 2 OCH 3 ; R 5 is H, halogen atom, —CH 2 COOH or OH; R 6 and R 7 are hydrogen, t-butyl or pyrolidyl; R 8 is hydrogen or lower alkyl; R 9 is alkyl or thienyl; R 10 is lower alkyl) or a pharmaceutically acceptable salt.

  乙醚和酰胺衍生物被披露，其由以下式(I)及其药用可接受盐所代表，并且对于糖尿病的治疗是有用的。 1 （在以下情况下，附加条件为：(i) 当A为—O—时，n为2或3 (ii) 当A为 2 时，n为1或2。R 3 为OH—，CH 3 SO 2 NH—，CF 3 SO 2 NH—，CH 3 SO 2 NHCH 2 —，CF 3 SO 2 NHCH 2 —，HOOC—，CH 3 OOC—， 3 HOOC—CH 2 SO 2 NH—，CF 3 —CH 2 SO 2 NH—， 4 R 8 —NHSO 2 —，R 8 —NHSO 2 —CH 2 —，HOOC—CH 2 —O—，HSO 3 N═CH—，或R 9 —SO 2 NHCO—； R 4 为H，OH，O-烷基或O—CH 2 OCH 3 ； R 5 为H，卤原子，—CH 2 COOH或OH； R 6 和R 7 为氢，叔丁基或吡咯烷基； R 8 为氢或较低烷基； R 9 为烷基或噻吩基； R 10 为较低烷基） 或药用可接受盐。
• METHOD FOR SYNTHESIZING OPTICALLY ACTIVE a-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL] ACETAMIDE COMPOUND AND AMINO ACID
  申请人：HAMARI CHEMICALS, LTD.

  公开号：US20160102045A1

  公开（公告）日：2016-04-14

  Objects of the present invention are to provide an industrially applicable method for producing an optically active α-amino acid in high yield and in a highly enantioselective manner, to provide a simple production method of an optically active α,α-disubstituted α-amino acid, and to provide an intermediate useful for the above production methods of an optically active α-amino acid and an optically active α,α-disubstituted α-amino acid. The present invention provides a production method of an optically active α-amino acid or a salt thereof, the production method comprising introducing a substituent into the α carbon in the α-amino acid moiety of a metal complex represented by the following Formula (1): by an alkylation reaction, an aldol reaction, the Michael reaction, or the Mannich reaction, and releasing an optically pure α-amino acid enantiomer or a salt thereof by acid decomposition of the metal complex.

  本发明的目的是提供一种在高产率和高对映选择性的方式下生产光学活性α-氨基酸的工业上适用的方法，提供一种简单的生产方法，用于光学活性α，α-二取代的α-氨基酸，并提供一种用于上述光学活性α-氨基酸和光学活性α，α-二取代的α-氨基酸生产方法的中间体。本发明提供了一种光学活性α-氨基酸或其盐的生产方法，该生产方法包括通过烷基化反应、醛醇反应、迈克尔反应或曼尼希反应将取代基引入以下式（1）所表示的金属配合物的α-氨基酸基团的α碳中，并通过酸分解金属配合物释放光学纯α-氨基酸对映体或其盐。
• Folate-modified cholesterol-bearing pullulan as a drug carrier
  申请人：Sunamoto Junzo

  公开号：US20070042970A1

  公开（公告）日：2007-02-22

  Folate modified cholesterol-bearing pullulan (FA-CHP) was synthesized by the reaction of folic acid γ-2-aminoethylamide and 4-nitorophenyl chloroformate-activated cholesterol-bearing pullulan, wherein folate and pullulan are connected through a NH—CH 2 —CH 2 —NH group. Approximately 0.5-1 folates are connected per about 100 glycoside units of pullulan. Then, several combinations of FA-CHP, cholesterol-bearing pullulan (CHP) and doxorubicin (DOX) mixture were tested for cancer selective cytotoxicity. A mixture of FA-CHP, CHP and DOX of 1:4:0.02 (weight ratio) gave sharp and selective damage to cells of a human epidermoid cancer KB known as expressing a high level of folate receptor. The same mixture inhibited the growth of HuH7 cells, which is a human hepatocellular carcinoma and is unknown as a folate receptor.

  叶酸修饰的胆固醇载体泊洛聚糖（FA-CHP）是通过叶酸γ-2-氨基乙酰胺和4-硝基苯基氯甲酸酯活化的胆固醇载体泊洛聚糖反应合成的，其中叶酸和泊洛聚糖通过一个NH—CH2—CH2—NH基团连接。每约100个葡糖苷单元中连接了大约0.5-1个叶酸。然后，对叶酸修饰的胆固醇载体泊洛聚糖（FA-CHP）、胆固醇载体泊洛聚糖（CHP）和阿霉素（DOX）混合物进行了多种组合的癌症选择性细胞毒性测试。FA-CHP、CHP和DOX的混合物比例为1:4:0.02（重量比）对人表皮癌KB细胞具有高叶酸受体表达水平的细胞造成了明显和选择性的损伤。同样的混合物抑制了HuH7细胞的生长，这是一种人类肝细胞癌，并且未知是否具有叶酸受体。
• Suppository and composition comprising at least one polyethylene glycol
  申请人：Anestic ApS

  公开号：US20020048601A1

  公开（公告）日：2002-04-25

  There is provided a suppository comprising at least one biocompatible polymer, wherein the biocompatible polymer is essentially non-biodegradable, and wherein the suppository essentially does not swell when contacted with an aqueous fluid. The suppository may further comprise a plurality of open cells at least partly separated from one another by an interpenetrating matrix comprising at least one biocompatible polymer in branched or crosslinked form. The plurality of interlinked, open cells are capable of containing an aqueous fluid, and the permeability of the suppository ensures that entry of body fluids into the open cells under practical circumstances occurs essentially without dehydration of mucousal membrane tissue contacting the suppository. The suppository furthermore preferably comprises a controlled release formulation.

  提供了一种含有至少一种生物相容性聚合物的栓剂，其中该生物相容性聚合物基本上不可生物降解，且当与水性液体接触时，该栓剂基本上不膨胀。该栓剂还可以进一步包括多个开放单元，这些单元至少部分地由相互穿插的基质分隔开，该基质包含至少一种分支或交联形式的生物相容性聚合物。这些互相连接的开放单元能够包含水性液体，而栓剂的渗透性确保体液进入开放单元时，在实际情况下基本上不会导致接触栓剂的粘膜组织脱水。此外，该栓剂最好包含控制释放配方。
• Esters of alkycarboxy amino acids as prodrugs of modulators of the kainate receptor
  申请人：Annovis, Inc.

  公开号：US20020115721A1

  公开（公告）日：2002-08-22

  Disclosed are prodrug compounds of a class of alkyl carboxy amino acid analogs of glutamic acid that act as specific regulators of the kainate EAA receptor cation channel. These compounds are useful for treating neurological, neuropsychological, neuropsychiatric, neurodegenerative, neuropsychopharmacological and functional disorders associated with excessive or insufficient activation of the kainate subtype of the ionotropic EAA receptors; treating cognitive disorders associated with deactivation, suboptimal activation or over-activation of the kainate receptor; alleviating pain and improving and enhancing memory, learning, and associated mental processes.

  本发明涉及一类丙基羧基氨基酸类谷氨酸类似物的前药化合物，它们作为特异性调节kainate EAA受体阳离子通道的调节剂。这些化合物可用于治疗与离子型EAA受体kainate亚型过度或不足激活相关的神经、神经心理、神经精神、神经退行性、神经精神药理学和功能障碍；治疗与kainate受体去活化、亚最佳激活或过度激活相关的认知障碍；缓解疼痛并改善和增强记忆、学习和相关的心理过程。