CAS: 87-81-0; (3S,4S,5R)-1,3,4,5,6-Pentahydroxyhexan-2-One

化学文摘社编号为87-81-0, 用于化学数据库的识别. 被监管机构普遍认为该物质是安全的(GRAS), 有助于其作为糖的替代品的吸引力.

结构式图片

相似化合物

7776-48-9 551-68-8 17598-82-2

上下游产品

CAS号2595-98-4 D-(+)-塔洛糖 | CAS号59-23-4 半乳糖 | CAS号67-47-0 5-羟甲基糠醛 | CAS号643-03-8 D-塔罗糖醇 | CAS号608-66-2 卫矛醇 | CAS号87-79-6 L-山梨糖 | CAS号57-48-7 果糖

合成工艺路线路线简述

  • 合成目标产物 D-Tagatose 主要起始原料 D-Galactose
  • 59-23-4 = 87-81-0
    反应条件:1.1 Reagents: 5′-Atp,Manganese(2+),Magnesium(2+) Catalysts: Hexokinase,L-Arabinose Isomerase Solvents: Water; 12 - 36 H,Ph 7.5,37 °C1.2 Reagents: Sodium Chloride,Silver Nitrate Solvents: Water; Ph 5.5,37 °C
    标题:Facile Enzymatic Synthesis Of Ketoses
    作者:Wen,Liuqing; Et Al
    参考文献:Angewandte Chemie 日期:2015 卷标:54(43) 页码:12654-12658]

    608-66-2 = 87-81-0
    反应条件:1.1 Reagents: Oxygen Catalysts: D-Iditol Dehydrogenase Solvents: Water
    标题:Bioconversion Of Sugars And Polyols Into Chiral Building Blocks For Chemical Synthesis
    作者:Huwig,A.; Et Al
    参考文献:Mededelingen - Faculteit Landbouwkundige En Toegepaste Biologische Wetenschappen (Universiteit Gent) 日期:1994 卷标:59 页码:2393-401]

    608-66-2 = 87-81-0
    反应条件:1.1 Solvents: Water
    标题:Conversion Of L-Rhamnose Into Ten Of The Sixteen 1- And 6-Deoxyketohexoses In Water With Three Reagents: D-Tagatose-3-Epimerase Equilibrates C3 Epimers Of Deoxyketoses
    作者:Gullapalli,Pushpakiran; Et Al
    参考文献:Tetrahedron Letters 日期:2010 卷标:51(6) 页码:895-898]

    63-42-3 = 87-81-0
    反应条件:1.1 Catalysts: Manganese,L-Arabinose Isomerase,β-Galactosidase; Ph 7,50 °C
    标题:Enzymatic Synthesis Of D-Tagatose From Lactose With The Combination Of β-Galactosidase And L-Arabinose Isomerase
    作者:Zhang,Liu-Quan; Et Al
    参考文献:Gongye Weishengwu 日期:2012 卷标:42(4) 页码:48-53]

    26566-61-0 = 87-81-0 + 3615-39-2
    反应条件:1.1 240 Min,Ph 12,70 °C
    标题:Recycling Preparation Of High-Purity Tagatose From Galactose Using One-Pot Boronate Affinity Adsorbent-Based Adsorption-Assisted Isomerization And Simultaneous Purification
    作者:Wang,Zihao; Et Al
    参考文献:Chemical Engineering Journal (Amsterdam 日期:2022 卷标:446]

    2595-98-4 = 87-81-0
    反应条件:1.1 Catalysts: Ribose Phosphate Isomerase Solvents: Water; 5 - 30 Min,Ph 7.5,65 °C1.2 Reagents: Hydrochloric Acid Solvents: Water
    标题:Novel Substrates Of A Ribose-5-Phosphate Isomerase From Clostridium Thermocellum
    作者:Yoon,Ran-Young; Et Al
    参考文献:Journal Of Biotechnology 日期:2009 卷标:139(1) 页码:26-32]

    63323-90-0 = 87-81-0
    反应条件:1.1 Reagents: Sodium Chloride,Silver Nitrate Solvents: Water; Ph 5.5,37 °C
    标题:Facile Enzymatic Synthesis Of Ketoses
    作者:Wen,Liuqing; Et Al
    参考文献:Angewandte Chemie 日期:2015 卷标:54(43) 页码:12654-12658]

    63-42-3 = 87-81-0
    反应条件:1.1 Reagents: Manganese Dichloride Catalysts: L-Arabinose Isomerase,β-Glycosidase Solvents: Water; 24 H,Ph 7.9,65 °C
    标题:Enzymatic Conversion Of D-Galactose To D-Tagatose: Heterologous Expression And Characterisation Of A Thermostable L-Arabinose Isomerase From Thermoanaerobacter Mathranii
    作者:Jorgensen,F.; Et Al
    参考文献:Applied Microbiology And Biotechnology 日期:2004 卷标:64(6) 页码:816-822]

    64044-51-5 = 87-81-0
    反应条件:1.1 Catalysts: Amberlyst 15,Hydrotalcite-2H2 (Mg6(Co3)[al(Oh)6]2(Oh)4.4H2O) Solvents: Dimethylformamide; 3 H,383 K2.1 Catalysts: Hydrotalcite-2H2 (Mg6(Co3)[al(Oh)6]2(Oh)4.4H2O) Solvents: Dimethylformamide; 3 H,373 K
    标题:One-Pot Synthesis Of Furans From Various Saccharides Using A Combination Of Solid Acid And Base Catalysts
    作者:Tuteja,Jaya; Et Al
    参考文献:Bulletin Of The Chemical Society Of Japan 日期:2012 卷标:85(3) 页码:275-281]

    59-23-4 = 87-81-0
    反应条件:1.1 Reagents: Sodium Hydroxide Catalysts: 3-[[[(2-Carboxypropyl)Oxidogermyl]Oxy]Oxidogermyl]-2-Methylpropanoic Acid,Poly[oxy[(2-Carboxypropyl)Hydroxygermylene]] (Hydrolyzed) Solvents: Water
    标题:Method For Isomerization Of Aldose To Ketose Using Organogermanium Compound As Promoter
    参考文献:Japan]

    608-66-2 = 87-81-0
    反应条件:1.1 Reagents: Nad,Oxygen Catalysts: Nadh Oxidase,Polyol Dehydrogenase (Nad(P)) Solvents: Water; 15 H,Ph 8,30 °C
    标题:D-Tagatose Manufacture Through Bio-Oxidation Of Galactitol Derived From Waste Xylose Mother Liquor
    作者:Sha,Feng; Et Al
    参考文献:Green Chemistry 日期:2018 卷标:20(10) 页码:2382-2391
Methyl 3,4-O-Isopropylidene-β-D-Tagatopyranoside置于溶剂黄146体系中,化学反应 0.17H,以100%的收率获得产物d-塔格糖
参考文献:由d-半乳糖衍生物合成d-塔格糖和1,5-脱水-D-塔格糖.
标题:由d-半乳糖衍生物合成d-塔格糖和1,5-脱水-D-塔格糖.
摘要:通过3,4,6-保护的d-吡喃半乳糖苷的氧化反应制得的3,4-O-异亚丙基-D-Lyxo-己吡喃糖苷-2-Ulose衍生物可以阴离子2,6-吡喃糖形式烷基化反应生成双-含2,5-二氧杂双环[2.2.2]辛烷环系统的糖苷.1-苄基-2-甲基双糖苷4B在进行催化氢解后,反应生成甲基d-Lyxo-己吡喃并-2-Uloside 10,以1:5-吡喃糖异构体9:8的混合物形式存在.计算并提供了NMR证据,以支持主要端基异构体具有α构型的假设.用nabh4还原9/10可得到甲基3,4-O-异亚丙基-β-D-塔格吡喃糖苷,可以水解为d-塔格糖.还介绍了从1,5-脱水d-半乳糖醇开始的1,5-脱水d-塔格糖的简单合成.
DOI:10.1016/0008-6215(95)00125-D

海关参考信息

专利信息


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-2019315790-A1
优先权日:2016-11-11
标题:Synthesis of d-allulose
发明人:KOCH TIMO JOHANNES; KIPPING FLORIAN; BUTZ STEFFEN; LESCH MARCEL; HÄSSLER THOMAS
权利人:PFEIFER & LANGEN GMBH & CO KG
摘要:The invention relates to a process for the synthesis of a product saccharide, preferably of D-allulose from an educt saccharide, preferably from D-fructose under heterogeneous or homogeneous catalysis which includes chemical and/or enzymatic catalysis. The synthesis is performed in at least two reactors that are arranged in series and the reaction product exiting the first reactor is subjected to chromatographic separation before it enters the second reactor. Preferably, the chromatographic separation is integrated in a simulated moving bed.

专利号:US-10005807-B2
优先权日:2013-04-12
标题 :Synthesis of sialylated/fucosylated human milk oligosaccharides
发明人:CHASSAGNE PIERRE; KHANZHIN NIKOLAY; HEDEROS MARKUS JONDELIUS; CHAMPION ELISE; MATWIEJUK MARTIN; DEKANY GYULA
权利人:GLYCOM AS
摘要:An achemo-enzymatic synthesis of oligosaccharides of formula 1 is presented wherein R is selected from —OH, —N 3 and —OR 6 wherein R 6 is selected from allyl optionally substituted by one or more methyl, propargyl optionally substituted by one or more methyl, 2-trimethylsilyl-ethyl, —(CH 2) n —NH 2 and —(CH 2) n —N 3 wherein integer n is to 10, preferably 2 or 3, R is selected from sialyl moiety, —SO 3 H and —CH(R)—COOH wherein R is selected from H, alkyl and benzyl, R 2 is selected from H and fucosyl, R 3 is selected from H and sialyl, R 4 is selected from H and fucosyl, provided that at least one of R 3 and R 4 is H, and A is a divalent carbohydrate linker, having important biological activities and significant commercial value for the pharmaceutical and food industry.

专利号:WO-9516049-A1
优先权日:1993-12-08
标题 :Catalytic chemo-enzymatic asymmetric synthesis of carbohydrates
发明人:WONG CHI-HUEY; SHARPLESS BARRY K
权利人:SCRIPPS RESEARCH INST; WONG CHI HUEY; SHARPLESS BARRY K
摘要:A stereoselective synthesis of carbohydrates employs two key stereoselective steps, viz. an osmium-catalyzed asymmetric dihydroxylation (AD) of an alkene to form an aldol intermediate and an aldolase-catalyzed aldol addition reaction wherein the aldol intermediate is elongated by the addition of a ketone. Moreover, ketoses having four new stereocenters can be synthesized without the use of chiral starting materials. The stereoselectivity of the asymmetric dihydroxylation (AD) reaction is determined by the cis or trans (Z or E) stereoisomeric configuration of the alkene and by the choice of AD-mix, i.e., an AD-mix-α or AD-mix-β. The stereoselectivity of the aldolase-catalyzed addition reaction is determined by the choice of aldolase and by the stereochemistry of the aldol intermediate. Four aldolases with broad substrate specificity are sufficient to produce all possible enantiomeric combinations of the two hydroxymethylene stereocenters formed during the aldol addition reaction. Accordingly, a synthetic scheme combining an osmium-catalyzed asymmetric dihydroxylation (AD) reaction and an aldolase-catalyzed aldol addition reaction enables direct access to a wide range of carbohydrate derivatives containing up to four new hydroxymethylene stereocenters.

专利号:WO-2014167537-A1
优先权日:2013-04-12
标题:Synthesis of sialylated/fucosylated oligosaccharides
发明人:KHANZHIN NIKOLAY; CHASSAGNE PIERRE; HEDEROS MARKUS; CHAMPION ELISE; MATWIEJUK MARTIN; DEKANY GYULA
权利人:GLYCOM AS
摘要:This invention relates to a chemo-enzymatic synthesis of oligosaccharidesof formula 1 wherein R is selected from -OH, -N 3 and -OR 6 wherein R 6 is selected from allyl optionally substituted by one or more methyl, propargyl optionally substituted by one or more methyl, 2-trimethylsilyl-ethyl, -(CH 2 ) n -NH 2 and -(CH 2 ) n -N 3 wherein integer n is to 10, preferably 2 or 3, R 1 is selected from sialyl moiety, -SO 3 H and -CH(R 5 )-COOH wherein R 5 is selected from H, alkyl and benzyl, R 2 is selected from H and fucosyl, R 3 is selected from H and sialyl, R 4 is selected from H and fucosyl, provided that one but only one of R 3 and R 4 is H, and A is selected from a bond and a divalent carbohydrate linker, having important biological activities and significant commercial value for the pharmaceutical and food industry.

专利号:EP-3835306-A1
优先权日:2019-12-13
标题:Microwave-assisted method for synthesis of oligo- and polysaccharides on solid phase
权利人:MAX PLANCK GESELLSCHAFT
摘要:The present invention relates to a method for synthesizing oligo- and polysaccharides using microwave radiation, in particular to a method and a device for automated synthesis of oligo- and polysaccharides.
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📌 第三方产品分析报告

✅ COA系统入驻 | 共享模式

主要参考文献

[参考文献]: Jeong Dw, Et Al. Trienzymatic Complex System For Isomerization Of Agar-Derived D-Galactose Into D-Tagatose As A Low-Calorie Sweetener. J Agric Food Chem. 2020;68(10):3195-3202.
[参考文献]: Daniel J Wichelecki, Et Al. Atp-Binding Cassette (Abc) Transport System Solute-Binding Protein-Guided Identification Of Novel D-Altritol And Galactitol Catabolic Pathways In Agrobacterium Tumefaciens C58. J Biol Chem. 2015 Nov 27;290(48):28963-76.
[参考文献]: Edwige Van Der Heiden, Et Al. Synthesis And Physicochemical Characterization Of D-Tagatose-1-Phosphate: The Substrate Of The Tagatose-1-Phosphate Kinase In The Phosphotransferase System-Mediated D-Tagatose Catabolic Pathway Of Bacillus Licheniformis. J Mol Microbiol Biotechnol. 2015;25(2-3):106-19.
[参考文献]: Moez Rhimi, Et Al. Production Of D-Tagatose, A Low Caloric Sweetener During Milk Fermentation Using L-Arabinose Isomerase. Bioresour Technol. 2011 Feb;102(3):3309-15.
[参考文献]: Moez Rhimi, Et Al. The Acid-Tolerant L-Arabinose Isomerase From The Mesophilic Shewanella Sp. Ana-3 Is Highly Active At Low Temperatures. Microb Cell Fact. 2011 Nov 10:10:96.

合成参考文献


摘要:Ewing, T. A.; Fraaije, M. W.; van Berkel, W. J. H., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 3, 173.
参考文献:10.1007/bf02231375
摘要:Kogan E, Schapira A, Janowitz H, Adlersberg D. Management of patients with massive resection of the small intestine with special reference to the use of steroid hormones. Digestive Diseases and Sciences. 1958 Nov;3(11):844–56. doi: 10.1007/bf02231375.
参考文献:10.1007/s00253-004-1578-6
摘要:Jrgensen F, Hansen OC, Stougaard P. Enzymatic conversion of d-galactose to d-tagatose: heterologous expression and characterisation of a thermostable l-arabinose isomerase from Thermoanaerobacter mathranii. Applied Microbiology and Biotechnology. 2004 Jun 01;64(6):816–22. doi: 10.1007/s00253-004-1578-6.
参考文献:10.1016/j.jmb.2006.04.040
摘要:Manjasetty BA, Chance MR. Crystal structure of Escherichia coli L-arabinose isomerase (ECAI), the putative target of biological tagatose production. J Mol Biol. 2006 Jul 07;360(2):297–309. doi: 10.1016/j.jmb.2006.04.040.
参考文献:10.1007/s00253-014-5827-z
摘要:Kim BJ, Hong SH, Shin KC, Jo YS, Oh DK. Characterization of a F280N variant of L-arabinose isomerase from Geobacillus thermodenitrificans identified as a D-galactose isomerase. Appl Microbiol Biotechnol. 2014 Nov;98(22):9271–81. doi: 10.1007/s00253-014-5827-z.
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