N-(γ-glutamyl)methylamine | 3081-62-7

• 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: N-(γ-glutamyl)methylamine
• 英文别名: N5-methyl-L-glutamine；γ-L-glutamyl methylamide；N-Me-L-Gln；L-γ-glutamyl-methylamide；L-2-Amino-glutarsaeure-5-methylamid；L-Glutaminsaeure-5-methylamid；γ-Glu-methylamide；(2S)-2-amino-5-(methylamino)-5-oxopentanoate；(2S)-2-azaniumyl-5-(methylamino)-5-oxopentanoate
• CAS: 3081-62-7
• 化学式: C₆H₁₂N₂O₃
• mdl: MFCD20640839
• 分子量: 160.173
• InChiKey: ONXPDKGXOOORHB-BYPYZUCNSA-N

物化性质

• 熔点：
  202 °C (decomp)
• 沸点：
  431.0±40.0 °C(Predicted)
• 密度：
  1.211

计算性质

• 辛醇/水分配系数(LogP)：
  -3.9
• 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：
  92.4
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2924199090

反应信息

• 作为反应物：
  描述：

  N-(γ-glutamyl)methylamine 在 enzyme from the toxin of crotalus adamanteus 、 catalase 作用下， 生成 2-oxo-glutaric acid-5-methylamide
  参考文献：
  名称：

  Meister, Journal of Biological Chemistry, 1953, vol. 200, p. 571,572, 574

  摘要：

  DOI：
• 作为产物：
  描述：

  N²-benzyloxycarbonyl-N⁵-methyl-L-glutamine 在 钯 作用下， 生成 N-(γ-glutamyl)methylamine
  参考文献：
  名称：

  Hashizume, Nippon Nogeikagaku Kaishi, 1951, vol. 25, p. 127,129

  摘要：

  DOI：

文献信息

• γ-Glutamyl Transfer Reactions by Glutaminase from<i>Pseudomonas nitroreducens</i>IFO 12694 and Their Application for the Syntheses of Theanine and γ-Glutamylmethylamide
  作者：Takashi TACHIKI、Takeshi YAMADA、Katsushige MIZUNO、Masashi UEDA、Ju-ichi SHIODE、Hiroshi FUKAMI

  DOI：10.1271/bbb.62.1279

  日期：1998.1

  In a mixture containing γ-glutamyl donor (donor) and γ-glutamyl acceptor (acceptor), the glutaminase of Pseudomonas nitroreducens IFO 12694 simultaneously catalyzed a γ-glutamyl transfer reaction and hydrolysis of the donor. The variation of the activities responding to the concentration of glutathione and glycylglycine indicated that the enzyme might be classified in a group of glutaminases that shows hydrolysis prior to transfer reaction. On the other hand, the results with glutamine and ethylamine or methylamine indicated that the enzyme was active in the transfer reaction with suppressed hydrolysis of glutamine, and suggested the possibility of using the reaction for producing γ-glutamylethylamide (theanine) or γ-glutamylmethylamide (γ-GMA). In fact, in a mixture containing high concentrations of substrates (0.7 M glutamine, 1.5 M ethylamine or methylamine) and 0.5 unit/ml glutaminase (borate buffer pH 11), 270 mM (47 g/L) theanine or 250 mM (38 g/L) γ-GMA was formed in 7 h of incubation at 30°C.

  在一混合物中，含有γ-谷氨酰供体（供体）和γ-谷氨酰受体（受体），Pseudomonas nitroreducens IFO 12694的谷氨酰胺酶同时催化γ-谷氨酰转移反应和供体的裂解。谷胱甘肽和甘氨酰甘氨酸浓度对活性的变化表明，该酶可能属于一类谷氨酰胺酶，表现出裂解优先于转移反应。另一方面，谷氨酰胺和乙胺或甲胺的结果表明，该酶在转移反应中活跃，而谷氨酰胺的裂解被抑制，这提示了利用该反应生产γ-谷氨酰乙胺（茶氨酸）或γ-谷氨酰甲胺（γ-GMA）的可能性。实际上，在高浓度底物（0.7 M谷氨酰胺，1.5 M乙胺或甲胺）和0.5单位/毫升谷氨酰胺酶（硼酸盐缓冲液pH 11）的混合物中，在30°C下孵育7小时，形成了270 mM（47 g/L）的茶氨酸或250 mM（38 g/L）的γ-GMA。
• Molecular Cloning and Characterization of γ-Glutamyltranspeptidase from<i>Pseudomonas nitroreducens</i>IFO12694
  作者：Masashi IMAOKA、Shigekazu YANO、Masashi OKUMURA、Takao HIBI、Mamoru WAKAYAMA

  DOI：10.1271/bbb.100199

  日期：2010.9.23

  γ-Glutamyltranspeptidase from Pseudomonas nitroreducens IFO12694 (PnGGT) exhibited higher hydrolytic activity than transfer activity, as compared with other γ-glutamyltranspeptidases (GGTs). PnGGT showed little activity towards most of l-amino acids and towards glycyl-glycine, which is often used as a standard γ-glutamyl accepter in GGT transfer reactions. The preferred substrates for PnGGT as a γ-glutamyl accepter were amines such as methylamine, ethylamine, and isopropylamine.

  与其它γ-谷氨酰转肽酶（GGT）相比，来自IFO12694的铜绿假单胞菌（PnGGT）展现出更高的水解活性而非转移活性。PnGGT对大多数L-氨基酸和常在GGT转移反应中用作标准γ-谷氨酰受体的甘氨酰甘氨酸表现出极低活性。作为γ-谷氨酰受体，PnGGT的优先底物为甲胺、乙胺和异丙胺等胺类。
• Trimeric Peptides for Use in Treating Obesity
  申请人：Conde Frieboes Kilian Waldemar

  公开号：US20080200366A1

  公开（公告）日：2008-08-21

  The present invention relates to novel peptide compounds which are effective in modulating one or more melanocortin receptor types, to the use of the compounds in therapy, to methods of treatment comprising administration of the compounds to patients in need thereof, and to the use of the compounds in the manufacture of medicaments. The compounds of the invention are of particular interest in relation to the treatment of obesity as well as a variety of diseases or conditions associated with obesity.

  本发明涉及新型肽化合物，其在调节一个或多个黑色素皮质素受体类型方面具有有效性，涉及将这些化合物用于治疗，涉及包括向需要这些化合物的患者进行给药的治疗方法，以及涉及将这些化合物用于制造药物。本发明的化合物在治疗肥胖以及与肥胖相关的各种疾病或病况方面具有特别兴趣。
• METHOD FOR SYNTHESIZING PEPTIDES IN CELL-FREE TRANSLATION SYSTEM
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US20200040372A1

  公开（公告）日：2020-02-06

  An objective of the present invention is to provide methods of synthesizing peptides containing structurally diverse amino acids using cell-free translation systems, which can accomplish excellent translational efficiency as compared to conventional techniques (the conventional techniques being methods which involve preparing aminoacyl-tRNAs which do not have protecting groups outside the translation systems without using ARS, and then adding the prepared aminoacyl-tRNAs into translation systems). In the present invention, it was found that amino acid-containing peptides can be synthesized efficiently by protecting an amino acid linked to tRNA with an appropriate protecting group, and then performing the step of deprotecting the protecting group of the amino acid linked to tRNA and the step of peptide translation from a template nucleic acid in a cell-free translation system in parallel.

  本发明的一个目标是提供使用无细胞翻译系统合成含有结构多样的氨基酸的肽的方法，这些方法可以实现与传统技术相比出色的翻译效率（传统技术是指涉及在翻译系统外部准备没有保护基的氨酰-tRNA而不使用ARS的方法，然后将准备好的氨酰-tRNA添加到翻译系统中）。在本发明中，发现通过用适当的保护基保护与tRNA连接的氨基酸，然后并行进行去保护氨基酸与tRNA连接的保护基的步骤和从模板核酸进行肽翻译的步骤，可以高效地合成含有氨基酸的肽。
• Peptide Tyrosinase Activators
  申请人：Escape Therapeutics, Inc.

  公开号：US20150152139A1

  公开（公告）日：2015-06-04

  Peptides that increase melanin synthesis are provided. These peptides include pentapeptides YSSWY, YRSRK, and their variants. The peptides may activate the enzymatic activity of tyrosinase to increase melanin synthesis. The pharmaceutical, cosmetic, and other compositions including the peptides are also provided. The methods of increasing melanin production in epidermis of a subject are provided where the methods include administering compositions comprising an amount of one or more peptides effective to increase the melanin production. The methods also include treating vitiligo or other hypopigmentation disorders with compositions including one or more peptides.

  提供了增加黑色素合成的肽类。这些肽包括五肽YSSWY、YRSRK及其变体。这些肽可能激活酪氨酸酶的酶活性，以增加黑色素的合成。还提供了包括这些肽的制药、化妆品和其他组合物。提供了一种增加受试者表皮黑色素产生的方法，其中方法包括给予含有一种或多种肽的组合物的有效量以增加黑色素的产生。这些方法还包括使用包括一种或多种肽的组合物治疗白癜风或其他低色素症。