CAS: 3226-65-1; (2S)-2-Amino-4-(Methylsulfinyl)Butanoic Acid

该化合物是基氨基酸L-甲基硫离子碱的氧化形式,其特点是在含硫化合物的侧链中添加氧原子,这种改变增强了其稳定性并改变了其反应性,使其在生化和制药研究中具有价值,成为氧化应激研究,蛋白改变分析和代谢路径调查中的一个关键中间体.它在红氧化调节和细胞信号中所起的作用进一步强调了其在实验应用中的重要性.L-甲基硫氧化物通常用于酶学实验,生物标志研究,并因其定义明确的化学特性和在生物系统中的相关性而成为参考标准.

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CAS号59-51-8 DL-蛋氨酸 | CAS号31418-44-7 methiononitrile... | CAS号63-68-3 L-蛋氨酸 | CAS号1492-24-6 L-2-氨基丁酸 | CAS号56-84-8 L-天门冬氨酸 | CAS号7314-32-1 L-蛋氨酸砜 | CAS号14857-77-3 L-同型半胱氨酸 | CAS号63-68-3 L-蛋氨酸 | CAS号820-10-0 DL-蛋氨酸砜 | CAS号838-07-3 2 '-脱氧-5-甲基胞苷 | CAS号59-51-8 DL-蛋氨酸 | CAS号3054-52-2 2-benzamido-4-m...

合成工艺路线路线简述

    📜L-蛋氨酸置于5-Ethyl-3-Methyl-4A-Hydroxy-4A,5-Dihydrolumiflavin,一水合肼体系中,用 2,2,2-三氟乙醇 作为反应溶剂,35.0 °C,101.33 Kpa 条件下,反应 4.0H,以95%的收率获得产物l-蛋氨酸亚砜
    参考文献:5-乙基-4A-羟基异恶嗪的绿色制备及其在催化需氧氧化中的应用
    标题:5-乙基-4A-羟基异恶嗪的绿色制备及其在催化需氧氧化中的应用
    摘要:异咯嗪环系统存在于自然界中的黄素辅因子中,模拟它们的氧化还原催化是开发可持续催化氧化反应的重要任务.尽管 5-乙基-4A-羟基异恶嗪是用于此类目的的最有希望的催化剂候选者之一,但到目前为止,它们在实验室和工业合成化学中的应用非常有限,大概是由于缺乏容易,安全的制备方法,而且价格便宜.在本次交流中,我们介绍了一种从 3,7,8,10-四甲基异恶嗪 (1) 制备 5-乙基-4A-羟基-3,7,8,10-四甲基异恶嗪 (1Etoh) 的环境友好且实用的制备方法,其中常规合成要求,包括 (I) 在惰性条件下操作,(II) 危险或昂贵的化学品,(Iii) 不稳定中间体的分离,已全部溶解.此外,我们还提出了 1Etoh 可以作为 Baeyer-Villiger 氧化以及在合适条件下以分子氧 (O2) 作为末端氧化剂的磺化氧化的有效催化剂,这是第一份关于 5-烷基催化的有氧氧化的报道. 4A-羟基异恶嗪.
    DOI:10.1002/ejoc.201801865

    海关参考信息

    专利信息


    专利号:US-12421534-B2
    优先权日:2021-11-10
    标 题 :Engineered enzymes and method for the synthesis of diverse tyrosine analogs
    发明人:ALMHJELL PATRICK J; ARNOLD FRANCES H
    权利人:CALIFORNIA INST OF TECHN
    摘要:Provided herein is an engineered tryptophan synthase β-subunit (TrpB) that catalyzes the synthesis of tyrosine, tyrosine analogs, or salts thereof. Also provided herein are methods for preparing tyrosine, tyrosine analogs, or a salt thereof using the engineered TrpB described herein.

    专利号:US-6376649-B1
    优先权日:1998-12-18
    标题 :Methods for the synthesis of α- hydroxy-β-amino acid and amide derivatives
    发明人:SEMPLE JOSEPH E; LEVY ODILE E
    权利人:CORVAS INT INC
    摘要:Methods for the synthesis of alpha-hydroxy-beta-amino acid and amide derivatives and alpha-ketoamide derivatives and novel derivatives made by these methods are provided. These methods involve reacting a N-terminally blocked (protected) aminoaldehyde with an isonitrile and a carboxylic acid to give an amino-alpha-acyloxy carboxamide. The acyloxy group may be removed to give the derivative. Alternatively the protecting group is removed and acyl shift occurs to give the derivative. These derivatives are useful in the synthesis of compounds such as peptidyl alpha-ketoamides and alpha-hydroxy-beta-carboxylic acid and amide derivatives. Certain of these compounds have been reported to have activity as inhibitors of proteases, such as serine proteases and cysteine proteases.

    专利号:US-2024067694-A1
    优先权日:2021-01-04
    标 题:Synthesis of teduglutide
    发明人:GANGA RAMU VASANTHAKUMAR; PATIL NITIN; SUVARNA DEEPA SHANKAR
    权利人:BIOCON LTD
    摘要:The present invention provides for novel synthetic approach of solid phase synthesis of peptides with C-terminal Aspartic acid by anchoring the side chain carboxylic group of aspartic acid to the solid support to avoid the formation of various impurities and thus resulting in higher yield and ease the purification process. The present invention further provides the usage of free amino acids and reducing agents as antioxidants in the cleavage cocktail to negate the formation of oxidative impurities formed during the global cleavage and isolation of the peptide from solid support.

    专利号:US-9938509-B2
    优先权日:2010-12-08
    标 题 :Biocatalysts and methods for the synthesis of armodafinil
    发明人:ANG EE LUI; ALVIZO OSCAR; BEHROUZIAN BEHNAZ; CLAY MICHAEL D; COLLIER STEVEN J; EBERHARD ELLEN D; FAN FU; SONG SHIWEI; SMITH DEREK J; WIDEGREN MAGNUS; WILSON ROBERT; XU JUNYE; ZHU JUN
    权利人:CODEXIS INC
    摘要:The present invention relates to non-naturally occurring polypeptides useful for preparing armodafinil, polynucleotides encoding the polypeptides, and methods of using the polypeptides. The non-naturally occurring polypeptides of the present invention are effective in carrying out biocatalytic conversion of the (i) 2-(benzhydrylsulfinyl)acetamide to (−)-2-[(R)-(diphenylmethyl)sulfinyl]acetamide (armodafinil), or (ii) benzhydryl-thioacetic acid to (R)-2-(benzhydrylsulfinyl)acetic acid, which is a pivotal intermediate in the synthesis of armodafinil, in enantiomeric excess.

    专利号:US-11571456-B2
    优先权日:2017-05-23
    标题 :Process for the linear synthesis of gram-positive class II bacteriocins and compositions and uses thereof
    发明人:BÉDARD FRANÇOIS; BIRON ÉRIC; HAMMAMI RIADH; FLISS ISMAIL
    权利人:UNIV LAVAL
    摘要:A process for the linear synthesis of a gram-positive class II bacteriocin or a variant thereof is disclosed herein. The process comprises the stepwise addition of selected amino acids to a solid support; pseudoproline positioning and reopening; and cleavage of the gram-positive class II bacteriocin or the variant thereof from the solid support to provide a linear gram-positive class II bacteriocin or variant thereof; and in situ disulfide bond formation. Various applications and uses of the synthetic bacteriocins are also disclosed. The synthetic process can also be used to synthesize variants of bacteriocins by the selective substitution of one or more amino acids and/or additions and/or deletions of selected amino acids.

    专利号:EP-0790982-B1
    优先权日:1994-06-17
    标 题 :Methods of synthesis of peptidyl argininals
    发明人:WEBB THOMAS R; REINER JOHN E; TAMURA SUSAN Y; RIPKA WILLIAM C; DAGNINO RAYMOND JR; NUTT RUTH F
    权利人:CORVAS INT INC
    摘要:This invention provides solution-phase and solid-phase methods for the synthesis of peptidyl argininals and to novel reagents useful therein, which have formula (I), wherein R1 is selected from the group consisting of hydrogen, benzyloxycarbonyl, isonicotinyloxycarbonyl, 2-chlorobenzyloxycarbonyl, 4-methoxybenzyloxycarbonyl, t-butoxycarbonyl, t-amyloxycarbonyl, isobornyloxycarbonyl, adamantyloxycarbonyl, 2-(4-biphenyl)-2-propyloxycarbonyl, 9-fluorenylmethoxycarbonyl and methylsulfonylethoxycarbonyl; R2 is selected from the group consisting of alkyl of 1 to about 12 carbon atoms and aralkyl of about 7 to about 15 carbon atoms, either of which is optionally substituted with hydroxy or -CO-Y, wherein Y is hydroxy, alkoxy of 1 to about 12 carbon atoms, aralkoxy of about 7 to about 15 carbon atoms, O-polymeric support or NH-polymeric support; R3 is selected from the group consisting of hydrogen, Fmoc, nitro, benzyloxycarbonyl, t-butoxycarbonyl and adamantyloxycarbonyl; and R4 is selected from the group consisting of hydrogen, alkyl of 1 to about 12 carbon atoms, aryl of about 6 to about 14 carbon atoms and aralkyl of about 7 to about 15 carbon atoms; and salts thereof.

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    合成参考文献


    参考文献:10.1023/a:1016059902645
    摘要:Gitlin G, Tsarbopoulos A, Patel ST, Sydor W, Pramanik BN, Jacobs S, Westreich L, Mittelman S, Bausch JN. Isolation and characterization of a monomethioninesulfoxide variant of interferon alpha-2b. Pharm Res. 1996 May;13(5):762–9. doi: 10.1023/a:1016059902645.
    参考文献:10.1007/s002530100548
    摘要:Or-Rashid MM, Onodera R, Wadud S. Biosynthesis of methionine from homocysteine, cystathionine and homoserine plus cysteine by mixed rumen microorganisms in vitro. Applied Microbiology and Biotechnology. 2001 Jun 01;55(6):758–64. doi: 10.1007/s002530100548.
    参考文献:10.1074/jbc.m400604200
    摘要:Vougier S, Mary J, Dautin N, Vinh J, Friguet B, Ladant D. Essential Role of Methionine Residues in Calmodulin Binding to Bordetella pertussis Adenylate Cyclase, as Probed by Selective Oxidation and Repair by the Peptide Methionine Sulfoxide Reductases. Journal of Biological Chemistry. 2004 Jul;279(29):30210–8. doi: 10.1074/jbc.m400604200.
    参考文献:10.1016/j.freeradbiomed.2009.11.020
    摘要:Lancellotti S, De Filippis V, Pozzi N, Peyvandi F, Palla R, Rocca B, Rutella S, Pitocco D, Mannucci PM, De Cristofaro R. Formation of methionine sulfoxide by peroxynitrite at position 1606 of von Willebrand factor inhibits its cleavage by ADAMTS-13: A new prothrombotic mechanism in diseases associated with oxidative stress. Free Radic Biol Med. 2010 Feb 01;48(3):446–56. doi: 10.1016/j.freeradbiomed.2009.11.020.
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