CAS: 10257-28-0; (3R,4S,5R,6R)-6-(Hydroxymethyl)Tetrahydro-2H-Pyran-2,3,4,5-Tetraol

该化合物是一种六碳单色细胞,具体地说是一种异丙二醇,是D-甘甘蓝的缩微胶,是一种循环型的甘蓝,主要以阳性成形形式存在,有六人环状结构.糖的特征是白色晶体外观,在水中可溶解,便于生物过程使用.D-甘二醇在各种代谢途径中发挥着关键作用,是乳糖,牛奶中发现的糖的成分.它也参与合成甘蓝蛋白和甘蓝,有助于细胞识别和信号.分子有多种氢氧(-OH)组,有助于其反应和形成氢结合的能力,影响其溶解性以及与其他生物分子的相互作用.D-甘二甲酚在营养和生物化学中都很重要,其衍生物被用于各种工业应用,包括食品和药品.

结构式图片

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合成工艺路线路线简述

    📜乳糖置于bacillus Circulans β-Galactosidase,水体系中,用 叔丁醇 用作溶剂,化学反应生成D-吡喃葡萄糖
    参考文献:Bacillus Circulans β-Galactosidase Catalyses The Synthesis Of N-Acetyl-Lactosamine In A Hydro-Organic Medium Via A Steady-State Ordered Bi Bi Reaction Mechanism
    标题:Bacillus Circulans β-Galactosidase Catalyses The Synthesis Of N-Acetyl-Lactosamine In A Hydro-Organic Medium Via A Steady-State Ordered Bi Bi Reaction Mechanism
    摘要:Starting From A Galactosyl Donor,The Beta-Galactosidase From Bacillus Circulans (Lactoles (R) L3; Bc Beta Gal) Catalyses The Transgalactosylation Of N-Acetyl-D-Glucosamine (Glcnac) In Hydro-Organic Media,Leading To The Synthesis Of N-Acetyl-Lactosamine (Lacnac). The Aim Of This Study Was To Determine The Kinetic Properties Of Lacnac Synthesis And Sought To Highlight The Effect Of The Organic Solvent On The Enzyme Kinetic Parameters. Analyses Of Enzyme Kinetics Were Performed In Aqueous Solutions And Water/tert-Butanol Mixtures. A Steady-State Ordered Bi Bi Mechanism Was Characterised For The Transgalactosylation Of Glcnac Catalysed By Bc Beta Gal In Water/tert-Butanol (70:30,V/v) Mixtures,Starting From O-Nitrophenyl-Beta-D-Galactopyranoside (Onpg) As A Galactosyl Donor. Moreover,Tert-Butanol Was Shown To Have Various Effects On The Kinetic Parameters Of The Total Transformation Of Onpg And Lactose Catalysed By Bc Beta Gal,Which Led Us To Liken This Solvent To A Noncompetitive Inhibitor Towards The Former And A Competitive Inhibitor Towards The Latter. (C) 2011 Elsevier B.V. All Rights Reserved.
    Doi:10.1016/j.Molcatb.2011.11.023

    海关参考信息

    专利信息


    专利号:WO-8800592-A1
    优先权日:1986-07-18
    标题:DIASTEROSELECTIVE STRECKER SYNTHESIS OF alpha-AMINOACIDS FROM GLYCOSYLAMINE DERIVATES
    发明人:KUNZ HORST; SAGER WILFRIED; PFRENGE WALDEMAR; DECKER MATHIAS
    权利人:CELAMERCK GMBH & CO KG
    摘要:O-acyl-protected glycosylamines, in particular 2,3,4,6-tetra-O-pivaloyl-beta-D-galactopyranosylamine (1), their preparation and their use for the diastereoselective synthesis of alpha-aminoacids. With compounds such as (1), one can obtain by Strecker synthesis high yields and high diastereomer surplus. The direction of the asymmetric induction can be determined by the selection of the solvent. This type of synthesis is particularly effective when carried with Lewis acid catalysts. One obtains also high yields and high diastereoselectivity during Ugi four component synthesis facilitated by Lewis acids by using amines such as (1).

    专利号:US-12188072-B2
    优先权日:2018-03-19
    标题 :Compositions and methods for rapid in vitro synthesis of bioconjugate vaccines in vitro via production and N-glycosylation of protein carriers in detoxified prokaryotic cell lysates
    发明人:JEWETT MICHAEL CHRISTOPHER; STARK JESSICA CAROL; DELISA MATTHEW P; JAROENTOMEECHAI THAPAKORN
    权利人:UNIV NORTHWESTERN; UNIV CORNELL
    摘要:Disclosed are methods, systems, components, and compositions for cell-free synthesis of glycosylated carrier proteins. The glycosylated carrier proteins may be utilized in vaccines, including anti-bacterial vaccines. The glycosylated carrier proteins may include a bacterial polysaccharide conjugated to a carrier, which may be utilized to generate an immune response in an immunized host against the polysaccharide conjugated to the carrier. The glycosylated carrier proteins may be synthesized in cell-free glycoprotein synthesis (CFGpS) systems using prokaryote cell lysates that are enriched in components for glycoprotein synthesis such as oligosaccharyltransferases (OSTs) and lipid-linked oligosaccharides (LLOs) including OSTs and LLOs associated with synthesis of bacterial O antigens.

    专利号:WO-0142264-A1
    优先权日:1999-12-10
    标 题 :Method for the synthesis of sialylated oligosaccharide donors
    发明人:MEHTA SEEMA; GILBERT MICHEL; WAKARCHUK WARREN W; WHITFIELD DENNIS M
    权利人:CA NAT RESEARCH COUNCIL; MEHTA SEEMA; GILBERT MICHEL; WAKARCHUK WARREN W; WHITFIELD DENNIS M
    摘要:A method for the synthesis of aryl thioglycosides comprising a sialylated residue of β-D-galactose is disclosed. The method consists of preparing by a chemical synthesis a non-sialylated aryl thioglycoside, and enzymatically sialylating the latter with a sialic acid in the presence of a suitable sialyltransferase. The sialylated aryl thioglycoside is then chemically derivatized by standard procedures, to provide a derivative suitable for use as a donor in chemical syntheses of sialylated oligosaccharides. The derivatized sialylated aryl thioglycosides are prepared in high yields, due to reduced number of chemical and purification steps involved in the process. Derivatized aryl thioglycosides useful as building blocks for the synthesis of biologically active sialylated oligosaccharides are also disclosed.

    专利号:US-2022395800-A1
    优先权日:2019-11-04
    标题:Device for automated synthesis of oligo- and polysaccharides
    发明人:SEEBERGER PETER H; DANGLAD FLORES JOSE; LE MAI HOANG KIM; PARDO VARGAS ALONSO; SLETTEN ERIC; SALWICZEK MARIO
    权利人:MAX PLANCK GESELLSCHAT ZU RFERDERUNG DER WSS E V; GlycoUniverse GmbH & Co KG&A
    摘要:The present invention generally relates to automated synthesis technology, and more particularly, to a device and method for automated synthesis of oligo- and polysaccharides on a solid support. In particular the present invention relates to a device for automated synthesis of oligo- and polysaccharides on a solid support comprising a reaction vessel, a reagent storing component, a reagent delivery system, a cooling device for cooling reaction vessel, and a pre-cooling device for pre-cooling the reagents to be supplied.

    专利号:US-2004058888-A1
    优先权日:2000-01-13
    标题:Methods for synthesis of alpha-d-gal (1~>3) gal-containing oligosaccharides
    发明人:BORNAGHI LAURENT; DEKANY GYULA; DRINNAN NICHOLAS BARRY; PAPAGEORGIOU JOHN; WEST MICHAEL LEO
    摘要:This invention relates to reagents and methods for synthesis of biologically active di- and tri-saccharides comprising α-D-Gal(1→3)-D-Gal. In particular the invention provides novel reagents, intermediates and processes for the solution or solid phase synthesis of α-D-galactopyranosyl-(1→3)-D-galactose, and derivatives thereof. In one preferred embodiments the invention provides a protected monosaccharide building block of general formula (II): in which R 3 is methoxy or methyl; R 1 is H, benzoyl, pivaloyl, 4-chlorobenzoyl, acetyl, chloroacetyl, levulinoyl, 4-methylbenzoyl, benzyl, 3,4-methylenedioxybenzyl, 4-methoxybenzyl, 4-chlorobenzyl, 4-acetamidobenzyl, or 4-azidobenzyl; and R 2 is H, Fmoc, benzoyl, pivaloyl, 4-chlorobenzoyl, acetyl, chloroacetyl, levulinoyl, 4-methylbenzoyl, benzyl, 3,4-methylenedioxybenzyl, 4-methoxybenzyl, 4 -chlorobenzyl, 4-acetamidobenzyl, or 4-azidobenzyl.

    专利号:US-10751419-B2
    优先权日:2014-05-01
    标题:Method for synthesis of reactive conjugate clusters
    发明人:MIGAWA MICHAEL T; YU JINGHUA; WAN W BRAD; PATEL SAYTEN P; VASQUEZ GUILLERMO; KINBERGER GARTH A; PRAKASH THAZHA P; SETH PUNIT P; SWAYZE ERIC E
    权利人:IONIS PHARMACEUTICALS INC
    摘要:Provided herein are improved methods for the synthesis of reactive conjugate clusters and intermediates used in such methods. In particular, improvements are provided that enhance the synthesis of reactive conjugate clusters by reducing the number of synthetic steps required. The reactive conjugate clusters prepared using the improved methods don't include any transacylation impurities that are formed using existing methods. The improved methods also provide an increase in overall yield and a cost benefit over existing methods.

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    合成参考文献


    参考文献:10.1111/j.1469-0691.2009.03065.x
    摘要:Castagnola E, Furfaro E, Caviglia I, Licciardello M, Faraci M, Fioredda F, Tomà P, Bandettini R, Machetti M, Viscoli C. Performance of the galactomannan antigen detection test in the diagnosis of invasive aspergillosis in children with cancer or undergoing haemopoietic stem cell transplantation. Clin Microbiol Infect. 2010 Aug;16(8):1197–203. doi: 10.1111/j.1469-0691.2009.03065.x.
    参考文献:10.1021/jf9040047
    摘要:Spadiut O, Nguyen TT, Haltrich D. Thermostable variants of pyranose 2-oxidase showing altered substrate selectivity for glucose and galactose. J Agric Food Chem. 2010 Mar 24;58(6):3465–71. doi: 10.1021/jf9040047.
    参考文献:10.3390/md9060952
    摘要:Costa LS, Fidelis GP, Telles CBS, Dantas-Santos N, Camara RBG, Cordeiro SL, Costa MSSP, Almeida-Lima J, Melo-Silveira RF, Oliveira RM, Albuquerque IRL, Andrade GPV, Rocha HAO. Antioxidant and antiproliferative activities of heterofucans from the seaweed Sargassum filipendula. Mar Drugs. 2011;9(6):952–66.
    参考文献:10.1128/jb.103.1.153-158.1970
    摘要:Dunn JH, Wolk CP. Composition of the Cellular Envelopes of Anabaena cylindrica. J Bacteriol. 1970 Jul;103(1):153–8. doi: 10.1128/jb.103.1.153-158.1970.
    参考文献:10.1371/journal.pone.0021784
    摘要:Saha R, Suthers PF, Maranas CD. Zea mays iRS1563: A Comprehensive Genome-Scale Metabolic Reconstruction of Maize Metabolism. PLoS ONE. 2011 Jul 06;6(7):e21784. doi: 10.1371/journal.pone.0021784.
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