CAS: 15548-60-4; (2S,3R,4S,5S,6R)-2-((5-Bromo-4-Chloro-1H-Indol-3-yl)Oxy)-6-(Hydroxymethyl)Tetrahydro-2H-Pyran-3,4,5-Triol

该化合物是一种合成化合物,在分子生物学中广泛用作染色基质,特别是用于检测-gluclonodase活性;该化合物具有一种与一个无粉结构相连的凝光拉线,以溴和氯原子替代的凝胶结构;其化学结构允许其在有-gluculonidase的情况下进行水解,从而释放出一种可视化为蓝色沉淀剂的蛋白衍生物,使该物质对于其化学染色和报告基因分析具有价值;X-Gluc在有机溶剂中可溶解,并在适当的储存条件下表现出稳定性;必须谨慎地处理这一化合物,因为如果浸泡或吸入,可能会对健康造成危害;

结构式图片

相似化合物

7240-90-6 107021-38-5 125229-64-3

上下游产品

(N-acetyl-5-bromo-4-chloroindol-3-yl) 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 1-acetyl-5-bromo-4-chloroindolin-3-one 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide H,1'H-[2,2']biindolylidene-3,3'-dione5,5'-dibromo-4,4'-dichloro-1H,1'H-[2,2']biindolylidene-3,3'-dione

合成工艺路线路线简述

    在 吗啉,四(三苯基膦)钯,Sodium Methylate,Silver(I) Acetate,Potassium Carbonate体系中,用 四氢呋喃,甲醇 用作溶剂,化学反应 0.58H,反应生成5-溴-4-氯-3-吲哚基-Beta-D-吡喃葡糖苷
    参考文献:吲哚乙酸酯作为吲哚氧基糖苷的方便中间体
    标题:吲哚乙酸酯作为吲哚氧基糖苷的方便中间体
    摘要:使用可扩展的路线以极好的收率获得了具有不同卤化物取代模式的吲哚酸甲酯和烯丙酯.这些关键中间体的相转移糖基化是用各种糖基卤化物进行的.随后温和的银介导的脱羧作用,然后是 Zemplen 脱乙酰作用,以非常好的总产率得到吲哚酚苷.吲哚酚苷是酶筛选和酶活性监测的成熟和广泛使用的工具.过去,它们的合成一直很困难,因此这种新方法导致了各种有用的结构.
    Doi:10.1002/ejoc.201301198

    海关参考信息

    专利信息


    专利号:US-2024009104-A1
    优先权日:2021-02-09
    标 题:Process for extraction and hemi-synthesis of pyranoanthocyanins and skincare cosmetic formulations containing them
    发明人:REIS FERNANDES IVA LUZIA; DA SILVA OLIVEIRA PINTO DA SILVA JOANA ALEXANDRA; DA CRUZ BATISTA MATEUS NUNO FILIPE; PEREIRA DE FREITAS VICTOR ARMANDO; COUTO OLIVEIRA HELDER JOSÉ; CARNEIRO ARAUJO PAULA ALEXANDRA; RODRIGUES CORREIA PATRICIA; MARTINS PEREIRA ANA RITA
    权利人:UNIV DO PORTO; REQUIMTE REDE DE QUIM E TECNOLOGIA
    摘要:A process of extraction of anthocyanins from different foodstuffs or by-products, and their conversion into pyranoanthocyanins compounds, which can be used as pigments having new colors and improved stability to be incorporated into skincare formulations in particular anti-ageing and sun-protection formulations. Cosmetic formulations having the pigments with improved properties of UV protection and moisturizing, anti-dark spots, anti-wrinkles and wound-healing, which can be associated with interesting colors ranging from red to blue depending on the selected pigments in the composition and in the formula composition. The present invention is in the area of organic chemistry, biochemistry, pharmacology and cosmetics for skincare.

    专利号:US-7078194-B2
    优先权日:1995-12-12
    标 题 :Methods and compositions for synthesis of oligosaccharides using mutant glycosidase enzymes
    发明人:WITHERS STEPHEN G; MACKENZIE LLOYD; WANG QINGPING
    权利人:UNIV BRITISH COLUMBIA
    摘要:Mutant glycosidase enzymes are formed in which the normal nucleophilic amino acid within the active site has been changed to a nonnucleophilic amino acid. These enzymes cannot hydrolyze disaccharide products, but which can still form them. Using this enzyme, oligosaccharides are synthesized by preparing a mixture of an &agr;glycosyl fluoride and a glycoside acceptor molecule; enzymatically coupling the &agr.glycosyl fluoride to the glycoside acceptor molecule to form a glycosyl glycoside product using the mutant glycosidase enzyme; and recovering the glycosyl glycoside product. Particular enzymes include a mutant form of Agrobacterium &bgr.Glucosidase in which the normal glutamic acid residue at position 358 is replaced with an alanine residue.

    专利号:EP-0870037-B1
    优先权日:1995-12-12
    标题 :Methods and compositions for synthesis of oligosaccharides using mutant glycosidase enzymes
    发明人:WITHERS STEPHEN G; MACKENZIE LLOYD; WANG QINGPING
    权利人:UNIV BRITISH COLUMBIA
    摘要:Mutant glycosidase enzymes are formed in which the normal nucleophilic amino acid within the active site has been changed to a non-nucleophilic amino acid. These enzymes cannot hydrolyze disaccharide products, but can still form them. Using this enzyme, oligoeaccharides are synthesized by preparing a mixture of an alpha -glycosol fluoride and a glycoside acceptor molecule; enzymatically coupling the alpha -glycosol fluoride to the glycoside acceptor molecule to form a glycosol glycoside product using the mutant glycosidase enzyme; and recovering the glycosyl product. The enzymes to be used are mutant forms of human or porcine alpha -amylase or yeast alpha -glucosidose having two catalytically active amino acids with carboxylic acid side claims within the active site, in the wild-type enzyme, with one of these amino acids being replaced by a different amino acid.

    专利号:US-5716812-A
    优先权日:1995-12-12
    标 题:Methods and compositions for synthesis of oligosaccharides, and the products formed thereby
    发明人:WITHERS STEPHEN G; MACKENZIE LLOYD; WANG QINGPING
    权利人:UNIV BRITISH COLUMBIA
    摘要:Mutant glycosidase enzymes are formed in which the normal nucleophilic amino acid within the active site has been changed to a non-nucleophilic amino acid. These enzymes cannot hydrolyze disaccharide products, but can still form them. Using this enzyme, oligosaccharides are synthesized by preparing a mixture of an alpha -glycosyl fluoride and a glycoside acceptor molecule; enzymatically coupling the alpha -glycosyl fluoride to the glycoside acceptor molecule to form a glycosyl glycoside product using the mutant glycosidase enzyme; and recovering the glycosyl glycoside product. Particular enzymes include a mutant form of Agrobacterium beta -Glucosidase in which the normal glutamic acid residue at position 358 is replaced with an alanine residue.

    专利号:US-2003100749-A1
    优先权日:1995-12-12
    标题:Methods and compositions for synthesis of oligosaccharides using mutant glycosidase enzymes

    专利号:CN-115916995-A
    优先权日:2020-05-13
    标题:Efficient synthesis of omega-glycosides and alkyl glycosides
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    ✅ COA系统入驻 | 共享模式

    主要参考文献

    [参考文献]: H Arakawa, Et Al. Chemiluminescent Assay Of Various Enzymes Using Indoxyl Derivatives As Substrate And Its Applications To Enzyme Immunoassay And Dna Probe Assay. Anal Biochem. 1991 Dec;199(2):238-42.
    [参考文献]: J P Horwitz, Et Al. Substrates For Cytochemical Demonstration Of Enzyme Activity. I. Some Substituted 3-Indolyl-Beta-D-Glycopyranosides. J Med Chem. 1964 Jul:7:574-5.
    [参考文献]: R Gossrau, Et Al. Histochemical Detection Of Alpha-D-Glucosidases And Their Molecular Forms With 5-Br-4-Cl-3-Indoxyl-Alpha-D-Glucoside. Histochemistry. 1987;86(4):397-404.
    [参考文献]: W D Watkins, Et Al. Novel Compound For Identifying Escherichia Coli. Appl Environ Microbiol. 1988 Jul;54(7):1874-5.

    合成参考文献


    参考文献:10.1007/s12010-008-8146-y
    摘要:Bhiri F, Chaabouni SE, Limam F, Ghrir R, Marzouki N. Purification and biochemical characterization of extracellular beta-glucosidases from the hypercellulolytic Pol6 mutant of Penicillium occitanis. Appl Biochem Biotechnol. 2008 May;149(2):169–82. doi: 10.1007/s12010-008-8146-y.
    参考文献:10.1007/978-1-62703-221-6_12
    摘要:Audenaert D, De Rybel B, Nguyen L, Beeckman T. Small-molecule screens to study lateral root development. Methods Mol Biol. 2013;959():189–95. doi: 10.1007/978-1-62703-221-6_12.
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