CAS: 53-57-6; Nadph

该化合物是一种代用标记的-氮丁胺二烯酸磷酸酯(NADPH)形式,其中用取代了4个氢原子.这种同位素标签的化合物在数量质谱和核磁共振研究中广泛用作内部标准,确保代谢和酶研究的高度精确性.它与本地的NADPH的结构性相似性在提供不同的检测信号的同时尽量减少干扰. β-NADPH-d4在追踪重毒反应,研究酶动能学和研究细胞代谢途径方面特别有用. 代谢标签的代谢性标签可以增强稳定性,减少代谢的折叠,从而成为在复杂的生物基质中准确量化的可靠工具.

结构式图片

MSDS等安全信息

    上下游产品

    NADP nicotinamide adenine dinucleotide phosphate D-glucose 6-phosphate L-glutamine NADP NADPH D-sorbitol pregnanedione

    合成工艺路线路线简述

    • 合成目标产物 Nadph 主要起始原料 β-Nicotinamide Mononucleotide And Adenosine Triphosphate
    • 56-81-5 = 53-57-6 + 373-44-4
      反应条件:1.1R:I-Prnh2,S:H2O,8 H,25°C,Ph 8
      标题:Transforming Inert Cycloalkanes Into α,ω-Diamines By Designed Enzymic Cascade Catalysis
      作者:By Zhang,Zhongwei Et Al
      参考文献:Angewandte Chemie 日期:2023 卷标:62(16) 页码:E202215935]

      53-84-9 + 328-50-7 = 53-57-6 + 58-68-4 + 56-86-0
      反应条件:1.1R:Hco2- na+,R:(Nh4)2So4,C:1449222-31-4,S:H2O,1.5 H,< 40°C,Ph 7.4; 1 H,< 40°C,Ph 7.41.2R:Phncs,R:Et3N,S:Mecn,1 H,Rt
      标题:The Visible-Light-Driven Transfer Hydrogenation Of Nicotinamide Cofactors With A Robust Ruthenium Complex Photocatalyst
      作者:By Dong,Wenjin Et Al
      参考文献:Green Chemistry 日期:2020 卷标:22(7) 页码:2279-2287]

      53-59-8 = 53-57-6
      反应条件:1.1R:N(Ch2Ch2Oh)3,C:1366596-70-4 (Reaction Product With Carboxy-Functionaliz),C:121596-51-8,S:H2O,S:Dmf,150 Min,Rt,Ph 7
      标题:A Photocatalyst/enzyme Couple That Uses Solar Energy In The Asymmetric Reduction Of Acetophenones
      作者:By Choudhury,Sumit Et Al
      参考文献:Angewandte Chemie 日期:2012 卷标:51(46) 页码:11624-11628]

      53-59-8 + 50-99-7 + 136592-00-2 = 53-57-6 + 477259-60-2 + 526-95-4
      反应条件:1.1C:9028-12-0,C:9028-53-9,S:H2O,S:Dmso,4 H,30°C,Ph 7.5
      标题:Application Of Biocatalysis Towards Asymmetric Reduction And Hydrolytic Desymmetrisation In The Synthesis Of A β-3 Receptor Agonist
      作者:By Badland,Matthew Et Al
      参考文献:Green Chemistry 日期:2011 卷标:13(10) 页码:2888-2894]

      53-59-8 = 53-57-6
      反应条件:1.1R:Cleland'S Reagent,R:N(Ch2Ch2Oh)3,R:Naod,S:H2O,4 H,Rt,Ph 8.9
      标题:Cofactor Mobility Determines Reaction Outcome In The Impdh And Gmpr (β-α)8 Barrel Enzymes
      作者:By Patton,Gregory C. Et Al
      参考文献:Nature Chemical Biology 日期:2011 卷标:7(12) 页码:950-958]

      53-59-8 = 53-57-6
      反应条件:1.1R:Zn (Myoglobin Complex),R:N(Ch2Ch2Oh)3,3.5 H,Rt,Ph 9; 7 D,Rt,Ph 9
      标题:Phototriggered Chemical Reduction Of Nadp+ By Zn-Reconstituted Myoglobin And Triethanolamine As A Sacrifical Donor
      作者:By Nishiyama,Katsuhiko Et Al
      参考文献:Chemistry Letters 日期:2005 卷标:34(7) 页码:1032-1033]

      53-59-8 = 53-57-6
      反应条件:1.1R:H2,C:9027-05-8,S:H2O,2 H,40°C,5 Bar,Ph 8
      标题:Membrane Aerated Hydrogenation: Enzymatic And Chemical Homogeneous Catalysis
      作者:By Greiner,Lasse Et Al
      参考文献:Advanced Synthesis & Catalysis 日期:2003 卷标:345(6+7) 页码:679-683]

      53-59-8 = 53-57-6
      反应条件:1.1R:H2,C:9027-05-8 (Immobilized),80°C1.2S:H2O,40°C,Ph 8.5
      标题:Utilization Of Adsorption Effects For The Continuous Reduction Of Nadp+ With Molecular Hydrogen By Pyrococcus Furiosus Hydrogenase
      作者:By Greiner,L. Et Al
      参考文献:Green Chemistry 日期:2003 卷标:5(6) 页码:697-700]

      53-59-8 = 53-57-6
      反应条件:1.1
      标题:Nadph Manufacture Using Permeabilized Microorganisms
      作者:By Silhankova,Ludmila And Hajek,Petr
      参考文献:Czech. 日期:From Czech.,266763,12 Jan 1990 卷标:266763 页码:12 Jan 1990]

      53-59-8 = 53-57-6
      反应条件:1.1R:C:15086-94-9 (Reaction Products With Aminomethylpolystyr),C:2920852-50-0,S:H2O
      标题:Polystyrene-Based Eosin-Y As A Photocatalyst For Solar Light-Mediated Nadh/nadph Regeneration And Organic Transformations
      作者:By Singh,Pooja Et Al
      参考文献:Reaction Chemistry & Engineering 日期:2023 卷标:8(5) 页码:1072-1082]

      53-59-8 = 53-57-6
      反应条件:1.1C:Cds
      标题:Protein-Mediated Biosynthesis Of Semiconductor Nanocrystals For Photocatalytic Nad(P)H Regeneration And Chiral Amine Production
      作者:By Bachar,Oren Et Al
      参考文献:Angewandte Chemie 日期:2022 卷标:61(23) 页码:E202202457]

      53-59-8 = 53-57-6
      反应条件:1.1R:HCL,S:H2O,10 Min
      标题:An Implantable Ionic Wireless Power Transfer System Facilitating Electrosynthesis
      作者:By Kim,Chong-Chan Et Al
      参考文献:Acs Nano 日期:2020 卷标:14(9) 页码:11743-11752]

      53-59-8 = 53-57-6
      反应条件:1.1
      标题:Development Of An Enzymatic Process For The Synthesis Of (S)-2-Chloro-1-(2,4-Dichlorophenyl) Ethanol
      作者:By Wei,Teng-Yun Et Al
      参考文献:Organic Process Research & Development 日期:2019 卷标:23(9) 页码:1822-1828]

      53-59-8 + 50-70-4 = 53-57-6
      反应条件:1.1R:Mgcl2,R:Na2Hpo4,R:Nh4Cl,R:Nacl,R:Mgso4,R:Kh2Po4,S:H2O,37°C
      标题:Co-Production Of Hydrogen And Ethanol By Pfka-Deficient Escherichia Coli With Activated Pentose-Phosphate Pathway: Reduction Of Pyruvate Accumulation
      作者:By Sekar,Balaji Sundara Et Al
      参考文献:Biotechnology For Biofuels 日期:2016 卷标:9 页码:95/1-95/11]

      53-59-8 = 53-57-6
      反应条件:1.1R:Me2Choh,S:H2O,30 Min,40°C,Ph 9.0
      标题:Contribution To Catalysis Of Ornithine Binding Residues In Ornithine N5-Monooxygenase
      作者:By Robinson,Reeder Et Al
      参考文献:Archives Of Biochemistry And Biophysics 日期:2015 卷标:585 页码:25-31]

      53-59-8 = 53-57-6
      反应条件:1.1C:9029-33-8,S:H2O,6°C,Ph 8.0
      标题:Structural Backgrounds For The Formation Of A Catalytically Competent Complex With Nadp(H) During Hydride Transfer In Ferredoxin-Nadp+ Reductases
      作者:By Sanchez-Azqueta,Ana Et Al
      参考文献:Biochimica Et Biophysica Acta 日期:2012 卷标:1817(7) 页码:1063-1071]

      87081-58-1 + 81201-97-0 + 110187-42-3 = 53-57-6 + 57-00-1 + 110-15-6 + 58-64-0 + 1310054-16-0
      反应条件:1.1R:Cleland'S Reagent,R:Mgcl2,R:R:R:R:R:R:H2O,R:Koh,R:Nh4Cl,C:56-65-5,C:Coenzyme Ii,C:9001-51-8,C:9001-40-5,C:9073-95-4,C:9023-83-0,C:9015-83-2,C:9026-23-7,C:9012-49-1,C:9024-93-5,C:9029-03-2,C:9030-25-5,C:9024-62-8,C:37278-21-0,C:9013-02-9,C:9029-12-3,C:9001-15-4,C:1927-31-7,S:H2O
      标题:Enzymatic De Novo Pyrimidine Nucleotide Synthesis
      作者:By Schultheisz,Heather L. Et Al
      参考文献:Journal Of The American Chemical Society 日期:2011 卷标:133(2) 页码:297-304]

      53-59-8 = 53-57-6
      反应条件:1.1S:872672-50-9,S:H2O,Ph 7
      标题:Ionic Liquids As Performance Additives For Electroenzymatic Syntheses
      作者:By Kohlmann,Christina Et Al
      参考文献:Chemistry - A European Journal 日期:2009 卷标:11692-11700 页码:S11692/1-S11692/11]

      53-59-8 = 53-57-6
      反应条件:1.1C:121596-52-9,S:H2O,Ph 7
      标题:Synthesis,Characterization And Application Of New Rhodium Complexes For Indirect Electrochemical Cofactor Regeneration
      作者:By Hildebrand,Falk Et Al
      参考文献:Advanced Synthesis & Catalysis 日期:2008 卷标:350(6) 页码:909-918]

      53-59-8 = 53-57-6
      反应条件:1.1R:D-Glucose,C:9028-53-9
      标题:α-Secondary Isotope Effects As Probes Of "Tunneling-Ready" Configurations In Enzymatic H-Tunneling: Insight From Environmentally Coupled Tunneling Models
      作者:By Pudney,Christopher R. Et Al
      参考文献:Journal Of The American Chemical Society 日期:2006 卷标:128(43) 页码:14053-14058]

      53-59-8 = 53-57-6
      反应条件:1.1R:Tris Buffer,R:H2,C:9027-05-8,S:774-48-1,1 H,40°C,2.3 Bar,Ph 8
      标题:Reaction Engineering Aspects Of Enzymic Manufacture Of Nadph In An Enzyme Membrane Reactor
      作者:By Mertens,Rita Et Al
      参考文献:Chemie Ingenieur Technik 日期:2005 卷标:77(5) 页码:609-616]

      53-59-8 = 53-57-6
      反应条件:1.1C:160261-98-3,S:H2O,20-25°C,Ph 8
      标题:Indirect Electrochemical Reduction Of Nicotinamide Coenzymes
      作者:By Vuorilehto,K. Et Al
      参考文献:Bioelectrochemistry 日期:2004 卷标:65(1) 页码:1-7]

      53-59-8 = 53-57-6
      反应条件:1.1R:H2,C:142903-68-2,S:H2O,3 H,40°C,70 Psi,Ph 8.3
      标题:Transition-Metal-Catalyzed Regeneration Of Nicotinamide Coenzymes With Hydrogen
      作者:By Wagenknecht,Paul S. Et Al
      参考文献:Organometallics 日期:2003 卷标:22(6) 页码:1180-1182
    β-烟酰胺腺嘌呤二核苷酸置于2,3-吡啶二甲酸,D-半乳糖-6-磷酸,Glucose-6-Phosphate Dehydrogenase From Saccharomyces Cerevisiae,Nicotinamide Adenine Dinucleotide Kinase From Bacillus Subtilis,5'-三磷酸腺苷体系中,用 Aq. Buffer 作为反应溶剂,化学反应生成 还原型辅酶ii(Nadph)四钠盐
    参考文献:发射合成辅因子:Atp,Nad+,Nadh,Nadp+ 和 Nadph Tza 类似物的酶促相互转化
    标题:发射合成辅因子:Atp,Nad+,Nadh,Nadp+ 和 Nadph Tza 类似物的酶促相互转化
    摘要:开发了一系列基于腺苷异噻唑并[4,3-D]嘧啶类似物(Tz A)的酶促转化,产生明显发射的同功能辅因子.烟酰胺腺苷酸转移酶将烟酰胺单核苷酸和tz Atp缩合产生n Tz Ad +,其可以被nad +激酶和atp或tz Atp酶促磷酸化为相应的n Tz Adp + .后者可以参与 Nadp 特异性偶联酶促转化,包括通过葡萄糖-6-磷酸脱氢酶转化为n Tz Adph,并通过谷胱甘肽还原酶再氧化为n Tz Adp + . N Tz Adp + / N Tz Adph循环可以通过荧光光谱进行实时监测.
    DOI:10.1002/anie.201711935

    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-5824472-A
    优先权日:1986-03-24
    标 题 :Process for the synthesis of sugar nucleotides using recombinant-DNA methods
    发明人:BETLACH MICHAEL R; DOHERTY DANIEL H; VANDERSLICE REBECCA W
    权利人:MONSANTO CO
    摘要:A recombinant-DNA mediated method for the synthesis of sugar nucleotides is disclosed. This method utilizes portable DNA sequences capable of directing the microbial synthesis of various enzymes that catalyze the synthesis of sugar nucleotides, including UDP-glucose, UDP-glucuronic acid and GDP-mannose. The sugar moieties of these sugar nucleotides may subsequently be incorporated into industrially-useful polysaccharides such as xanthan gum. It has been found that vectors containing the portable DNA sequences described herein are capable both of causing sugar nucleotide production in microorganisms previously incapable of such synthesis and of causing increased sugar nucleotide production in organisms capable of synthesizing small quantities of these compounds. In particular, plasmids pAS7, pAS9 and pTS13 are disclosed. These plasmids are capable of directing sugar nucleotide synthesis in various hosts, including Xanthomonas sp. such as X. campestris and other organisms such as E. coli and various Pseudomonas sp.

    专利号:US-10865390-B2
    优先权日:2018-02-12
    标 题 :Alcohol dehydrogenase mutant and application thereof in synthesis of diaryl chiral alcohols
    发明人:NI YE; ZHOU JIEYU; XU GUOCHAO; WANG YUE
    权利人:UNIV JIANGNAN
    摘要:The present disclosure discloses an alcohol dehydrogenase mutant and application thereof in synthesis of diaryl chiral alcohols, and belongs to the technical field of bioengineering. The alcohol dehydrogenase mutant of the present disclosure has excellent catalytic activity and stereoselectivity, and may efficiently catalyze the preparation of a series of chiral diaryl alcohols in R- and S-configurations. By coupling alcohol dehydrogenase of the present disclosure to glucose dehydrogenase or formate dehydrogenase, the synthesis of chiral diaryl alcohol intermediates of various antihistamines may be achieved. Compared with the prior art, a method for preparing diaryl chiral alcohols through asymmetric catalytic reduction using the alcohol dehydrogenase of the present disclosure has the advantages of simple and convenient operation, high substrate concentration, complete reaction and high product purity, and has great industrial application prospects.

    专利号:US-2025019732-A1
    优先权日:2023-07-07
    标 题:Method for chemical-biological cascade synthesis of l-phosphinothricin and mutants therefor
    发明人:XUE YAPING; CHENG FENG; ZOU SHUPING; XU JIANMIAO; ZHENG YUGUO
    权利人:UNIV ZHEJIANG TECHNOLOGY
    摘要:A method for chemical-biological cascade synthesis of L-phosphinothricin is carried out as follows: 3-(methylethoxyphosphinyl) ethyl propionate is synthesized by addition reaction from diethoxymethylphosphine and acrylic acid, then a condensation reaction is carried out with 3-(methylethoxyphosphinyl) ethyl propionate and sodium ethoxide as reactants, then the product is subjected to a hydrolysis reaction with diethyl oxalate to synthesize 4-(hydroxymethylphosphinyl)-2-oxobutyric acid, and finally, L-phosphinothricin is catalytically synthesized by taking 4-(hydroxymethylphosphinyl)-2-oxobutyric acid as a raw material, and using highly active and stable wet cells co-expressing phsophinothricin dehydrogenase and alcohol dehydrogenase or co-expressing a phsophinothricin dehydrogenase mutant and alcohol dehydrogenase as a biocatalyst, thereby solving the problems of existing L-phosphinothricin synthesis being tedious, low asymmetric amination reduction activity and poor stability.

    专利号:US-10822593-B2
    优先权日:2018-02-12
    标 题:Alcohol dehydrogenase mutant and application thereof in synthesis of diaryl chiral alcohols
    发明人:NI YE; ZHOU JIEYU; XU GUOCHAO; WANG YUE
    权利人:UNIV JIANGNAN
    摘要:The present disclosure discloses an alcohol dehydrogenase mutant and application thereof in synthesis of diaryl chiral alcohols, and belongs to the technical field of bioengineering. The alcohol dehydrogenase mutant of the present disclosure has excellent catalytic activity and stereoselectivity, and may efficiently catalyze the preparation of a series of chiral diaryl alcohols in R- and S-configurations. By coupling alcohol dehydrogenase of the present disclosure to glucose dehydrogenase or formate dehydrogenase, the synthesis of chiral diaryl alcohol intermediates of various antihistamines may be achieved. Compared with the prior art, a method for preparing diaryl chiral alcohols through asymmetric catalytic reduction using the alcohol dehydrogenase of the present disclosure has the advantages of simple and convenient operation, high substrate concentration, complete reaction and high product purity, and has great industrial application prospects.

    专利号:US-11053227-B2
    优先权日:2017-12-20
    标 题:Process for preparing intermediates for the synthesis of optically active beta-amino alcohols by enzymatic reduction and novel synthesis intermediates
    发明人:COLLI CORRADO; BERTOLINI GIORGIO; SADA MARA; GARIS FARIS; NISIC FILIPPO; BIANCHI ALDO; BIAGGI CINZIA; DI FABIO ROMANO; RONZONI SILVANO; BERTUOLO STEFANIA; PRANDI ADOLFO; MAIORANA STEFANO
    权利人:OLON SPA
    摘要:Subject-matter of the present invention is a process for preparing intermediates for the synthesis of optically active beta-amino alcohols by enzymatic reduction of the corresponding beta-amino ketones. Subject-matter of the invention are also said novel synthesis intermediates and the use thereof in the preparation of active pharmaceutical ingredients, among which vilanterol and the salts thereof.
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    主要参考文献


    1: Sameer H, Victor G, Katalin S, Henrik A. Elucidation of ligand binding and dimerization of NADPH:protochlorophyllide (Pchlide) oxidoreductase (POR) from pea (Pisum sativum L.) by structural analysis and simulations. Proteins. 2021 May 22. doi: 10.1002/prot.26151. Epub ahead of print.
    226:107864. doi: 10.1016/j.pharmthera.2021.107864. Epub ahead of print. 14(1):100. doi: 10.1186/s13068-021-01954-6.
    7: Abdel-Hady GN, Ikeda T, Ishida T, Funabashi H, Kuroda A, Hirota R. Engineering Cofactor Specificity of a Thermostable Phosphite Dehydrogenase for a Highly Efficient and Robust NADPH Regeneration System. Front Bioeng Biotechnol. 2021 Apr 1;9:647176. doi: 10.3389/fbioe.2021.647176.

    合成参考文献


    参考文献:10.1124/dmd.104.000034
    摘要:Karanam BV, Hop CE, Liu DQ, Wallace M, Dean D, Satoh H, Komuro M, Awano K, Vincent SH. In vitro metabolism of MK-0767 [(+/-)-5-[(2,4-dioxothiazolidin-5-yl)methyl]-2-methoxy-N-[[(4-trifluoromethyl) phenyl]methyl]benzamide], a peroxisome proliferator-activated receptor alpha/gamma agonist. I. Role of cytochrome P450, methyltransferases, flavin monooxygenases, and esterases. Drug Metab Dispos. 2004 Sep;32(9):1015–22. doi: 10.1124/dmd.104.000034.
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