CAS: 1187-84-4; S-Methyl-L-Cysteine

该化合物是一种含有氨基酸衍生物的硫,具有分子式C4H9NO2S.在结构上与L-cysteine相似,但以甲基硫代(-SH)组代替硫醇组(-SH),这种改变增强了其抗氧化的稳定性,使其在生化和制药研究中有所助益.SMC是含有硫代谢物合成的前体,并研究其在调节细胞再氧化平衡方面的潜在作用.其高纯度和定义明确的结构使其适合用于酶学,代谢研究以及作为分析化学的参考标准.

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合成工艺路线路线简述

    📜N-乙酰基-S-甲基-L-半胱氨酸置于n-Acetylornithine Deacetylase From Escherichia Coli,Cobalt(II) Chloride体系中,用 Aq. Phosphate Buffer 用作溶剂,化学反应 24.0H,反应生成S-甲基-L-半胱氨酸
    参考文献:通过 1H NMR 直接监测氨基酸底物的生物催化脱乙酰作用揭示了底物特异性的细节
    标题:通过 1H NMR 直接监测氨基酸底物的生物催化脱乙酰作用揭示了底物特异性的细节
    摘要:氨基酸是关键的合成构件,可以通过生物催化方法制备对映体纯形式.我们发现l-选择性鸟氨酸脱乙酰酶 Arge 催化多种n-酰基氨基酸底物的水解.该活性通过1 H NMR 光谱来揭示,该光谱监测了乙酸盐产物的清晰信号的出现.此外,该测定还使用可以采用不同旋转异构体构象的底物来探测生物催化剂的微妙结构选择性.
    Doi:10.1039/d1Ob00122A

    海关参考信息

    专利信息


    专利号:WO-2023039068-A1
    优先权日:2021-09-08
    标题:Compositions and methods for synthesis of peptide nucleic acid intermediates
    发明人:COULL JAMES M; GILDEA BRIAN D
    权利人:NEUBASE THERAPEUTICS INC
    摘要:The present disclosure provides intermediates for the synthesis of peptide nucleic acid (PNA) backbones and monomers, such as cyclic intermediates, and methods of making the same.

    专利号:US-7459443-B2
    优先权日:1999-04-08
    标 题 :Synthesis of biologically active compounds in cells
    发明人:SERGEEV PAVEL
    权利人:SERGEEV PAVEL
    摘要:This invention relates to a new method of synthesis of biologically active substances of determined structure directly in the cells of living organisms containing specific RNA or DNA molecules of determined sequence. The method is based on the hybridization of two or more oligomers bound with biologically inactive precursors of biologically active substances to specific RNA or DNA in vivo in the cells of living organisms. After hybridization of the oligomers to RNA or DNA the biologically inactive precursors bound to the 5′ and/or 3′ ends of the oligomers can interact with each other to make biologically active form of the substances. This changing of properties is due to chemical reactions which bind the biologically inactive precursors through a chemical bond into a biologically active form of the whole compound.

    专利号:US-2007088086-A1
    优先权日:1999-08-16
    标题 :Method of using synthetic L-Se-methylselenocysteine as a nutriceutical and a method of its synthesis
    发明人:SPALLHOLZ JULIAN E; REID TED W; WALKUP ROBERT D
    权利人:PHARMASE INC
    摘要:A synthesis of and use for L-Se-methylselenocysteine as a nutriceutical is described, based upon the knowledge that L-Se-methylselenocysteine is less toxic than L-selenomethionine towards normal cells. The synthesis proceeds by mixing N-(tert-butoxycarbonyl)-L-serine with a dialkyl diazodicarboxylate and at least one of a trialkylphosphine, triarylphosphine, and phosphite to form a first mixture that includes N-(tert-butoxycarbonyl)-L-serine β-lactone. Methyl selenol or its salt is mixed with the N-(tert-butoxycarbonyl)-L-serine β-lactone to form a second mixture that includes N-(tert-butoxycarbonyl)-Se-methylselenocysteine. The tert-butoxycarbonyl group is removed from the N-(tert-butoxycarbonyl)-Se-methylselenocysteine to form L-Se-methylselenocysteine. This synthesis significantly improves the manufacturability, manufacturing efficiency, and utility of this naturally occurring rare form of organic-selenium. L-Se-methylselenocysteine formed, for example, in this manner may be used as a nutriceutical for supplementation into the diets of humans or animals for various beneficial purposes, such as, for example, to prevent or reduce the risk of developing cancer.

    专利号:EP-1205471-A1
    优先权日:2000-10-02
    标题:A method of using synthetic L-SE-Methylselenocysteine as a nutriceutical and a method of its synthesis
    发明人:SPALLHOLZ JULIAN E; REID TED W; WALKUP ROBERT D
    权利人:PHARMASE INC
    摘要:A synthesis of and use of L-Se-methylselenocysteine as a nutriceutical isndescribed, based upon the knowledge that L-Se-methylselenocysteine is lessntoxic than L-selenomethionine towards normal cells. The synthesis proceedsnby mixing N-(tert-butoxycarbonyl)-L-serine with a dialkyl diazodicarboxylatenand at least one of a trialkylphosphine, triarylphosphine and phosphite to formna first mixture that includes N-(tert-butoxycarbonyl)-L-serine β-lactone.nMethyl selenol or its salt is mixed with the N-(tert-butoxycarbonyl)-L-serine β-lactonento form a second mixture that includes N-(tert-butoxycarbonyl)-Se-methylselenocysteine.nThe text butoxycarbonyl group is removed from the N-(tert-butoxycarbonyl)-Se-methylselenocysteinento form L-Se-methylselenocysteine.nThis synthesis significantly improves thenmanufacturability, manufacturing efficiency and utility of this naturallynoccurring rare form of organic-selenium. L-Se-methylselenocysteine formed,nfor example, in this manner may be used as a nutriceutical for supplementationninto the diets of humans or animals for various beneficial purposes, such as, fornexample, to prevent or reduce the risk of developing cancer.

    专利号:US-2020354404-A1
    优先权日:2019-05-09
    标 题 :Peptidomimetic agents, synthesis and uses thereof
    发明人:AL-ABED YOUSEF
    权利人:FEINSTEIN INSTITUTES FOR MEDICAL RESEARCH
    摘要:Compounds for use in synthesis of peptidomimetic agents; synthesis of peptidomimetic agents; peptidomimetic diagnostic and therapeutic agents; and uses of the compounds and peptidomimetic agents in drug discovery, diagnosis, prevention and treatment of diseases are described.

    专利号:US-2013243770-A1
    优先权日:2005-10-14
    标 题:Treating diabetes using inhibitors of il-1
    发明人:LAU JESPER
    权利人:NOVO NORDISK AS
    摘要:The present invention describes a method of treating diabetes or metabolic syndrome with a compound that inhibits (a) IL-1, (b) the synthesis of IL-1, or (c) the release of IL-1.

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    主要参考文献


    1: Rubino FM, Pitton M, Di Fabio D, Meroni G, Santaniello E, Caneva E, Pappini M, Colombi A. Measurement of S-methylcysteine and S-methyl-mercapturic acid in human urine by alkyl-chloroformate extractive derivatization and isotope-dilution gas chromatography-mass spectrometry. Biomed Chromatogr. 2011 Mar;25(3):330-43. doi: 10.1002/bmc.1451. Japanese. Japanese. doi: 10.1074/jbc.M110.167304. Epub 2010 Oct 5.
    7: Thompson JF, Gering RK. Biosynthesis of s-methylcysteine in radish leaves. Plant Physiol. 1966 Oct;41(8):1301-7.
    8: Zhao J, Ng CM, Chu IK, Siu KW, Hopkinson AC. Methionine, alpha-methylmethionine and S-methylcysteine radical cations: generations and dissociations in the gas phase. Phys Chem Chem Phys. 2009 Sep 21;11(35):7629-39. Japanese. Japanese. Epub 2005 Dec 7. Japanese.

    合成参考文献


    摘要:Faber, K.; Glueck, S. M., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 1, 438.
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