CAS: 556-27-4; (R)-3-((S)-Allylsulfinyl)-2-Aminopropanoic Acid

该化合物是含有硫的化合物,主要存在于大蒜()中,对许多健康惠益和典型芳香负责;它是无色,晶状物质,在水中溶解,具有略微苦味;Alliin是氨基酸cysteine的衍生物,被归类为二氧化硫;大蒜粉碎或切碎后,Alliin通过酶Alinase的行动被转化成Alicin,该酶是大蒜的发味和许多治疗特性的产物;Alliin本身因其潜在的健康惠益而闻名,包括抗微生物,抗炎和抗氧化作用,还因其在心血管健康中的作用和增强免疫系统的能力而进行研究;由于不稳定性,Alliin通常没有在加工的大蒜产品中找到大量此类产品,使新鲜大蒜成为这一化合物的更强大的来源.

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CAS号21593-77-1 S-烯丙基-L-半胱氨酸 | CAS号49621-03-6 DL-S-烯丙基半胱氨酸 | CAS号539-86-6 大蒜素 | CAS号127-17-3 丙酮酸 | CAS号17795-24-3 (2R)-2-氨基-3-(丙基... | CAS号23127-41-5 N-乙酰基-S-烯丙基-L-半胱氨酸 | CAS号21593-77-1 S-烯丙基-L-半胱氨酸 | CAS号124-38-9 二氧化碳 | CAS号7664-41-7 氨

合成工艺路线路线简述

    Methyl S-Allyl-L-Cysteinate置于双氧水,Sodium Methylate体系中,用 甲醇,水,乙腈 作为反应溶剂,化学反应 28.0H,反应生成 蒜氨酸
    参考文献:蒜氨酸和别蒜素的简单合成:X射线衍射分析及其绝对构型的确定.
    标题:蒜氨酸和别蒜素的简单合成:X射线衍射分析及其绝对构型的确定.
    摘要:开发了一种从大蒜中分离生物活性化合物蒜素的简单方法,以及在制备实验室规模上合成非对映体纯蒜素和别蒜素的方法.基于酶反应性,旋光分散性和圆二色性分析,确定了蒜氨酸和别丙氨酸中硫原子的绝对构型.将这些分析的结果进行比较,并结合对受保护的脲基丙氨酸衍生物的x射线衍射研究,分别发现了脲基丙氨酸和脲基丙氨酸中硫原子的s和r构型.此外,对于合成和天然蒜氨酸观测到相同的(1)h NMR光谱.天然蒜氨酸的绝对构型是首次根据NMR光谱和x射线坐标指定的.
    DOI:10.1021/acs.Jafc.5B05501

    海关参考信息

    专利信息


    专利号:US-2014357576-A1
    优先权日:2013-05-31
    标题:Methods for enhancement of muscle protein synthesis
    发明人:BREUILLE DENIS; STELLINGWERFF TRENT; MOORE DANIEL RYAN; OFFORD CAVIN ELIZABETH ANN; PHILLIPS STUART MARTIN
    权利人:NESTEC SA
    摘要:The present disclosure provides methods for enhancing muscle protein synthesis in an individual in need of same. Specifically, the present disclosure provides methods for enhancing muscle protein synthesis by enhancing myofibrillar muscle protein synthesis. The method includes administering to the individual a mixed macronutrient composition having (i) an amount of whey protein that is not capable of enhancing myofibrillar protein synthesis when ingested by itself and (ii) free leucine. The composition comprises at least about 5.0 g total leucine per dose.

    专利号:WO-2014009759-A3
    优先权日:2012-07-13
    标题 :Improvements in or relating to allium extracts
    发明人:BENNETT N; RAMSEY EDWARD DALHOUSIE
    权利人:LEPTREX LTD
    摘要:The present invention relates to improvements in or relating to Allium extracts. In particular, it relates to improvements in or relating to extending the therapeutic half- life or duration of Allium extracts. The invention also relates to the synthesis of certain thiosulfinate compounds, especially to the synthesis of methyl allyl thiosulfinate and allyl methyl thiosulfinate, in particular from either methiin or alliin alone or a mixture of both. The invention further relates to the synthesis of methyl allyl thiosulfinate, allyl methyl thiosulfinate, allicin, and methyl methyl thiosulfinate in a mixture with varying molar or mass ratios depending on the reaction conditions, in particular from either methiin or alliin alone or a mixture of both. A high yielding, optimized synthesis of allicin starts from alliin, whereas methyl methyl thiosulfinate is advantageously obtained from methiin. Also provided is a kit comprising methiin in a first container and/or alliin in a second container and an allinase source, in particular garlic powder in a third container. Finally, the invention provides a method of preparing a mixture of methyl allyl thiosulfinate, allyl methyl thiosulfinate, allyl allyl thiosulfinate (allicin) and methyl methyl thiosulfinate from methiin and pieces of an Allium species.

    专利号:US-2014294788-A1
    优先权日:2013-03-26
    标 题 :Methods for enhancing muscle protein synthesis following concurrent training
    发明人:BAILEY DAVID MARK; ZALTAS ERIC SCOTT; MOORE DANIEL RYAN; STELLINGWERFF TRENT
    权利人:NESTEC SA
    摘要:The present disclosure provides methods for enhancing muscle protein synthesis following physical exertion. In a general embodiment, a method for enhancing muscle protein synthesis following physical exertion is provided and includes administering to an individual a composition comprising from about 15 to about 35 g protein immediately following concurrent training. Programs for enhancing muscle adaptation resulting from concurrent training are also provided. The programs include providing a composition comprising from about 15 to about 35 g protein; and providing guidelines for consumption including a recommendation of the amount of the composition to consume immediately following concurrent training.

    专利号:US-7452701-B2
    优先权日:1998-11-24
    标 题:Methods for the preparation of β-amino acids
    发明人:FREY PERRY A; RUZICKA FRANK J
    权利人:WISCONSIN ALUMNI RES FOUND
    摘要:Purified β-amino acids are of considerable interest in the preparation of pharmacologically active compounds and industrial precursors. Although enantiomerically pure β-amino acids can be produced by standard chemical synthesis, this traditional approach is time consuming, requires expensive starting materials, and results in a racemic mixture which must be purified further. However, DNA molecules encoding lysine 2,3-aminomutase can be used to prepare β-amino acids by methods that avoid the pitfalls of chemical synthesis. The present invention provides a method of producing enantiomerically pure β-amino acids from α-amino acids comprising catalyzing the conversion of an α-amino acid to a corresponding β-amino acid by utilizing a lysine 2,3-aminomutase as the catalyst.

    专利号:US-2004053999-A1
    优先权日:1997-09-17
    标题 :Novel compounds and methods for synthesis and therapy
    发明人:BISCHOFBERGER NORBERT W; DAHL TERRENCE C; HITCHCOCK MICHAEL J M; KIM CHOUNG U; LEW WILLARD; LIU HONGTAO; MILLS ROGER G; WILLIAMS MATTHEW A
    摘要:Novel compounds are described. The compounds generally comprise an acidic group, a basic group, a substituted amino or N-acyl and a group having an optionally hydroxylated alkane moiety. Pharmaceutical compositions comprising the inhibitors of the invention are also described. Methods of inhibiting neuraminidase in samples suspected of containing neuraminidase are also described. Antigenic materials, polymers, antibodies, conjugates of the compounds of the invention with labels, and assay methods for detecting neuraminidase activity are also described.

    专利号:US-6225341-B1
    优先权日:1995-02-27
    标 题:Compounds and methods for synthesis and therapy
    发明人:BISCHOFBERGER NORBERT W; KIM CHOUNG U; LEW WILLARD; LIU HONGTAO; WILLIAMS MATTHEW A
    权利人:GILEAD SCIENCES INC
    摘要:Novel compounds are described. The compounds generally comprise an acidic group, a basic group, a substituted amino or N-acyl and a group having an optionally hydroxylated alkane moiety. Pharmaceutical compositions comprising the inhibitors of the invention are also described. Methods of inhibiting neuraminidase in samples suspected of containing neuraminidase are also described. Antigenic materials, polymers, antibodies, conjugates of the compounds of the invention with labels, and assay methods for detecting neuraminidase activity are also described.
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    主要参考文献


    1: Chen Z, Xu M, Wang C, Zhou H, Fan L, Huang X. Thermolysis kinetics and thermal degradation compounds of alliin. Food Chem. 2017 May 15;223:25-30. doi: 10.1016/j.foodchem.2016.12.011. Epub 2016 Dec 9. doi: 10.1111/tpj.12954. doi: 10.1021/acs.jafc.5b05501. Epub 2015 Dec 15. doi: 10.1016/j.jchromb.2014.02.037. Epub 2014 Mar 2. doi: 10.1107/S1399004714020938. Epub 2014 Oct 29. Chinese. pii: E1516.
    9: Nasim SA, Dhir B, Kapoor R, Fatima S, Mahmooduzzafar, Mujib A. Alliin obtained from leaf extract of garlic grown under in situ conditions possess higher therapeutic potency as analyzed in alloxan-induced diabetic rats. Pharm Biol. 2011 Apr;49(4):416-21. doi: 10.3109/13880209.2010.521163. Epub 2011 Mar 11. doi: 10.3892/or.2016.4628. Epub 2016 Feb 22. doi: 10.1155/2013/381815. Epub 2013 Dec 26.
    12: Tao D, Zhou B, Zhang L, Hu X, Liao X, Zhang Y. 'Laba' garlic processed by dense phase carbon dioxide: the relation between green colour generation and cellular structure, alliin consumption and alliinase activity. J Sci Food Agric. 2016 Jul;96(9):2969-75. doi: 10.1002/jsfa.7463. Epub 2015 Oct 21. doi: 10.3389/fpls.2014.00758. eCollection 2014.

    合成参考文献


    摘要:Grogan, G., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 3, 307.
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