CAS: 636-58-8; (S)-2-Amino-5-(((R)-1-Carboxy-2-Mercaptoethyl)Amino)-5-Oxopentanoic Acid

该化合物是一种由氨基酸谷颈酸和cysteine组成的二极酸,其特征是,在谷状酸碳箱基组和丙烯基氨基组之间存在伽马联系,使其有别于其他丙酸形式.该化合物在谷硫酮的生物合成中发挥着关键作用,该物质是细胞中一种重要的抗氧化剂,有助于防止氧化性压力. -L-Glutamyl-L-cystene通常存在于各种生物系统中,并且涉及细胞过程,如脱毒和细胞再氧化状态的调节等.该物质在水中溶解,在生理条件下呈现一种相对稳定的结构.该混合物对生物化学研究和潜在的治疗应用,特别是在与氧化性紧张有关的疾病方面,具有重大意义.其化学文摘社编号为636-58-8,用于化学数据库和监管环境中的识别.

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CAS号25830-77-7 N-邻苯二甲酰-L-谷氨酸酐 | CAS号100051-89-6 (R)-3-L-γ-gluta... | CAS号52-90-4 L-半胱氨酸 | CAS号142-47-2 谷氨酸钠 | CAS号23052-19-9 bis-gamma-gluta... | CAS号56-41-7 L-丙氨酸 | CAS号70-18-8 谷胱甘肽/5-L-谷氨酰-L-... | CAS号27025-41-8 L-谷胱甘肽(氧化型) | CAS号4510-09-2 N-benzyloxycarb... | CAS号52-90-4 L-半胱氨酸 | CAS号70-18-8 谷胱甘肽/5-L-谷氨酰-L-...

合成工艺路线路线简述

    📜N-邻苯二甲酰-L-谷氨酸酐置于硫化氢,Mercury(II) Diacetate,N,O-双(三甲基硅烷基)三氟乙酰胺,一水合肼,三乙胺体系中,用 甲醇,水 作为反应溶剂,化学反应 4.08H,反应生成 5-L-谷氨酰-L-半胱氨酸
    参考文献:Augmentation Of Human And Rat Lenticular Glutathione In Vitro By Prodrugs Of γ-L-Glutamyl-L-Cysteine
    标题:Augmentation Of Human And Rat Lenticular Glutathione In Vitro By Prodrugs Of γ-L-Glutamyl-L-Cysteine
    摘要:A Marked Age-Related Decrease In Glutathione (Gsh) Levels As Well As Depression Of Gamma-Glutamylcysteine Synthetase Activity Are Factors That Are Believed To Render The Aged Lens More Susceptible To Oxidative Stress And,Therefore,To Cataractogenesis. Providing Gamma-L-Glutamyl-L-Cysteine,The Dipeptide Precursor Of Gsh,Would Effectively Bypass The Compromised First Step In Its Biosynthesis And Should Protect The Lens From Gsh Depletion. Accordingly,Some Bioreversible Sulfhydryl-,Amino-,And C-Terminal Carboxyl-Protected Prodrug Forms Of This Dipeptide Were Prepared. Sulfhydryl Protection Was In The Form Of An Acetyl Thioester,While The Carboxyl Group Was Protected As The Ethyl Ester. These Prodrugs Were Evaluated For Their Gsh-Enhancing Activity In Cultured Human And Rat Lenses In Vitro Using An Assay That Measured The Incorporation Of [c-14]Glycine Into Lens Gsh. Ethyl S-Acetyl-Gamma-L-Glutamyl-L-Cysteinate (2) Raised Gsh Levels In Human Lenses By 25% And In Rat Lenses By >150%. These Data Suggest That 2 May Have Potential As An Anticataract Agent Since Ethyl Gamma-L-Glutamyl-L-Cysteinate (1A),The Des-S-Acetyl Analog Of 2,Had Been Shown (By Others) To Protect Against Experimental Rodent Cataracts. Gsh Augmentation By 1A Was 2% In Human Lenses And 25% In Rat Lenses,Considerably Less Than That Shown By 2.
    DOI:10.1021/jm950674Y

    海关参考信息

    专利信息


    专利号:US-2010279334-A1
    优先权日:2007-10-31
    标题 :Cyclodipeptide synthases (cdss) and their use in the synthesis of linear dipeptides
    发明人:SAUGUET LUDOVIC; THAI ROBERT; BELIN PASCAL; LECOQ ALAIN; GENET ROGER; PERNODET JEAN-LUC; GONDRY MURIEL
    权利人:KYOWA HAKKO BIO CO LTD; CENTRE NAT RECH SCIENT; UNIV PARIS SUD 11; COMMISSARIAT ENERGIE ATOMIQUE
    摘要:Use of CDSs in the synthesis of linear dipeptides, and applications thereof for the in vivo and in vitro synthesis of linear dipeptides, in particular Phe-Leu, Leu-Phe, Phe-Phe, Phe-Tyr, Tyr-Phe, Leu-Leu, Leu-Tyr, Tyr-Leu, Phe-Met, Met-Phe, Leu-Met, Met-Leu, Tyr-Met, Met-Tyr, Met-Met, Tyr-Tyr, Ile-Met, Met-Ile, Leu-Ile, Ile-Leu using the corresponding polynucleotides.

    专利号:US-RE40849-E
    优先权日:1998-04-30
    标题:Method of treatment of glutathione deficient mammals
    发明人:KELLER ROBERT H; KIRCHENBAUM DAVID W
    权利人:VIT IMMUNE L C
    摘要:Glutathione (GSH) is a tripeptide of extreme importance as a catalyst, reductan, and reactant. It can be depleted intracellulary either by forming a direct complex with an electrophilic agent (accomplished investigationally by agents such as bromobenzene or diethyl maleate), by way of inhibition of synthesis, or by subjecting cells to oxidant stress. Most cells, except for epithelia cells, do not have a direct transport capacity for intact GSH. Non-epithelial cells must either transport precursor substrates for GSH synthesis or salvage amino acids from circulating GSH for reuse in intracellular resynthesis. Dietary cysteine is a rate limiting substrate for the synthesis of glutathione and also inhibits GSH efflux. Although GSH is synthesized from precursors in virtually all cells, the liver is the main source of plasma GSH. Protection and support of liver function is paramount to elevating GSH levels. The disclosure is also of a unique combination of nutritional supplements including n-acetyl cysteine, vitamin C, l-glucosamine, n-acetyl d-glucosamine, quercitin, sylimarin, Alpha lipoic acid and high protein, low fat whey that are combined to support various bodily systems involved in glutathione synthesis, reutilization and storage; all intended to elevate glutathione concentration in the mammalian cell.

    专利号:US-7312049-B2
    优先权日:2005-06-14
    标题:Total amino acid stabilization during cell-free protein synthesis
    发明人:CALHOUN KARA ANNE; SWARTZ JAMES ROBERT
    权利人:UNIV LELAND STANFORD JUNIOR
    摘要:Compositions and methods are provided for the enhanced in vitro synthesis of protein molecules, by optimizing the metabolism of amino acids present in the reaction mix, preferably all amino acids in the reaction mixture. By performing synthesis with extracts from genetically modified microbial strains that are deficient in multiple amino acid metabolizing enzymes reduces the enzymatic activities responsible for catalyzing these reactions and improves the overall yield of synthesis.

    专利号:US-6531608-B2
    优先权日:1999-05-25
    标题:Various thiol complexes, processes for their synthesis and clinical applications
    发明人:PEARSON DON C; RICHARDSON KENNETH T
    权利人:CHRONORX LLC
    摘要:This invention relates to the synthesis of certain complexes of cysteine, N-acetylcysteine, N-(2-mercaptopropionyl)glycine, and L-2-oxothiazolidine-4-carboxylate and to the nutritional use of these and other related individual or complexed thiol-contributing glutathione predecessors. Clinical uses for these molecules and complexes in the beneficial modification of various physiological conditions and functions associated with aging, chronic glaucoma, diabetes mellitus, insulin resistance, macular degeneration, neurodegenerative diseases and vasoconstriction are described in particular.

    专利号:WO-2023183543-A1
    优先权日:2022-03-25
    标 题 :Chemoenzymatic synthesis of selenoneine and its analogs
    发明人:SEYEDSAYAMDOST MOHAMMAD; KAYROUZ CHASE
    权利人:UNIV PRINCETON
    摘要:Disclosed is a method for forming selenoneine or analogs thereof. The method may include phosphorylating sodium selenide to a selenophosphate, using adenosine triphosphate (ATP) and at least a first protein, generating a selenosugar by converting the selenophosphate using at least a second protein in the presence of a common sugar donor, and forming selenoneine or an analog thereof by combining the selenosugar with N,N,N-trimethyl-L- histidine or analogs thereof using at least a third protein. The method may include combining SenA, SenB, and SenC in an aqueous buffer at neutral pH and ambient temperature, and allowing SenA, SenB, and SenC to form selenoneine or an analog thereof in the presence of ATP, a common sugar donor, and sodium selenide.

    专利号:US-2005004225-A1
    优先权日:2003-04-16
    标题:Oxidoreductase inhibitors and methods of screening and using thereof
    发明人:BALENDIRAN GANESARATNAM K
    摘要:The present invention relates to 1) the design and synthesis of analogs to glutathione conjugates which bind to or interact with aldose reductase (AR) through unique conformations that are distinctly different from the substrates and inhibitors of AR which are members of sugar metabolism; 2) the screening of the analogs to identify those that interact with or inhibit or enhance the activity of AR; and 3) the use of AR ligands, AR inhibitors (AR antagonsits) or AR enhancer (AR agonists) in the detection of AR activity, the modulation of AR activity, and the treatment of conditions in a subject in need of modulating AR activity. Such conditions include but not limited to cardiovascular disease, diabetes, artheriosclerosis, cancer, neoplasm, obesity, cataract, retinopathy, keratopathy, nephropathy, neurosis, thrombosis, faulty union of corneal injury and neuropathy. Examples of the treatment include the use of fibrates as AR inhibitors to treat these conditions.

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    合成参考文献


    参考文献:10.1007/s10522-010-9262-y
    摘要:Robert L, Labat-Robert J, Robert AM. Genetic, epigenetic and posttranslational mechanisms of aging. Biogerontology. 2010 Aug;11(4):387–99. doi: 10.1007/s10522-010-9262-y.
    参考文献:10.2147/ceg.s17114
    摘要:Payne CM, Crowley-Skillicorn C, Bernstein C, Holubec H, Bernstein H. Molecular and cellular pathways associated with chromosome 1p deletions during colon carcinogenesis. Clin Exp Gastroenterol. 2011;4():75–119.
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