CAS: 838-07-3; 4-Amino-1-((2R,4S,5R)-4-Hydroxy-5-(Hydroxymethyl)Tetrahydrofuran-2-yl)-5-Methylpyrimidin-2(1H)-One

该化合物是一种经过修改的核核素,在将细胞素基置入2'脱氧细胞碘的5个位置时引入了一种甲基组,这种修改在遗传调节中发挥着关键作用,特别是在DNA甲基化过程中,它影响到基因表达和细胞分化.该化合物广泛用于分子生物学研究,包括关于DNA复制,修复和甲基化动态的研究.它的高度纯度和稳定性使它适合于将酶融入寡核素,支持合成生物学和肾学的应用.此外,5-甲基-2'-脱氧细胞碘是HPLC和质量光谱测定等分析技术的宝贵参考标准.

结构式图片

相似化合物

69075-47-4 951-77-9 4449-40-5

欧盟法规

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合成工艺路线路线简述

  • 合成目标产物 5-Methyl-2'-Deoxycytidine 主要起始原料 Thymidine
  • 50-89-5 = 838-07-3
    反应条件:1.1 Reagents: 1,8-Diazabicyclo[5.4.0]Undec-7-Ene,Phosphorus(1+),[3-(Hydroxy-Ko)-3H-1,2,3-Triazolo[4,5-B]Pyridinato]Tri-1-Pyrroli... Solvents: Dimethylformamide; 1 Min,Rt1.2 Reagents: Ammonium Hydroxide Solvents: Dimethylformamide; 2 H,Rt
    标题:An Efficient Pyaop-Based C4-Amination Method For Direct Access Of Oxidized 5-Methyl-2'-Deoxycytidine Derivatives
    作者:Zheng,Xiu-An; Et Al
    参考文献:Tetrahedron 日期:2018 卷标:74(49) 页码:7095-7101]

    = 838-07-3
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol
    标题:Novel Synthetic Route To 1-Substituted Cytosines
    作者:Ciszewski,Krzysztof; Et Al
    参考文献:Synthesis 日期:1995 卷标:(7) 页码:777-9]

    = 838-07-3
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Water
    标题:Development Of New Amination Reaction At 4-Position Of Pyrimidine Nucleosides
    作者:Tsuchiya,Katsutoshi; Et Al
    参考文献:Nucleic Acids Research Supplement 日期:2002 卷标:2 页码:135-136]

    554-01-8 + 951-78-0 = 838-07-3
    反应条件:1.1 Catalysts: Nucleoside Deoxyribosyltransferase Solvents: Water; 2 H,Ph 6.5,40 °C
    标题:Enzymatic Synthesis Of Nucleoside Analogues Using Immobilized 2'-Deoxyribosyltransferase From Lactobacillus Reuteri
    作者:Fernandez-Lucas,Jesus; Et Al
    参考文献:Applied Microbiology And Biotechnology 日期:2011 卷标:91(2) 页码:317-327]

    68-94-0 + 50-89-5 = 838-07-3
    反应条件:1.1 Catalysts: Nucleoside Deoxyribosyltransferase Solvents: Water; 2 H,Ph 6.5,40 °C2.1 Catalysts: Nucleoside Deoxyribosyltransferase Solvents: Water; 2 H,Ph 6.5,40 °C3.1 Catalysts: Nucleoside Deoxyribosyltransferase Solvents: Water; 2 H,Ph 6.5,40 °C
    标题:Enzymatic Synthesis Of Nucleoside Analogues Using Immobilized 2'-Deoxyribosyltransferase From Lactobacillus Reuteri
    作者:Fernandez-Lucas,Jesus; Et Al
    参考文献:Applied Microbiology And Biotechnology 日期:2011 卷标:91(2) 页码:317-327]

    68-94-0 + 958-09-8 = 838-07-3
    反应条件:1.1 Catalysts: Nucleoside Deoxyribosyltransferase Solvents: Water; 2 H,Ph 6.5,40 °C2.1 Catalysts: Nucleoside Deoxyribosyltransferase Solvents: Water; 2 H,Ph 6.5,40 °C3.1 Catalysts: Nucleoside Deoxyribosyltransferase Solvents: Water; 2 H,Ph 6.5,40 °C
    标题:Enzymatic Synthesis Of Nucleoside Analogues Using Immobilized 2'-Deoxyribosyltransferase From Lactobacillus Reuteri
    作者:Fernandez-Lucas,Jesus; Et Al
    参考文献:Applied Microbiology And Biotechnology 日期:2011 卷标:91(2) 页码:317-327]

    890-38-0 + 73-24-5 = 838-07-3
    反应条件:1.1 Catalysts: Nucleoside Deoxyribosyltransferase Solvents: Water; 2 H,Ph 6.5,40 °C2.1 Catalysts: Nucleoside Deoxyribosyltransferase Solvents: Water; 2 H,Ph 6.5,40 °C3.1 Catalysts: Nucleoside Deoxyribosyltransferase Solvents: Water; 2 H,Ph 6.5,40 °C
    标题:Enzymatic Synthesis Of Nucleoside Analogues Using Immobilized 2'-Deoxyribosyltransferase From Lactobacillus Reuteri
    作者:Fernandez-Lucas,Jesus; Et Al
    参考文献:Applied Microbiology And Biotechnology 日期:2011 卷标:91(2) 页码:317-327]

    = 838-07-3 + 50-89-5
    反应条件:1.1 Catalysts: Alkaline Phosphatase,Phosphodiesterase Solvents: Water
    标题:Design Of Highly Efficient And Selective Transfer Reaction Of Nitrosyl Group To Dc And Dmc Resulting In Specific Deamination
    作者:Ali,Monsur; Et Al
    参考文献:Nucleosides 日期:2005 卷标:24(5-7) 页码:721-724]

    20188-74-3 = 838-07-3
    反应条件:1.1 Reagents: Ammonia,Dimethyldioxirane Solvents: Acetone,Dichloromethane1.2 Reagents: Ammonia Solvents: Methanol
    标题:A New And Efficient Synthesis Of Cytidine And Adenosine Derivatives By Dimethyldioxirane Oxidation Of Thiopyrimidine And Thiopurine Nucleosides
    作者:Saladino,Raffaele; Et Al
    参考文献:Journal Of The Chemical Society 日期:1994 卷标:(21) 页码:3053-4]

    50-89-5 = 838-07-3
    反应条件:1.1 Reagents: Acetyl Chloride Solvents: Acetic Acid1.2 Reagents: Phosphorus Sulfide (P2S5) Solvents: Pyridine2.1 Reagents: Ammonia,Dimethyldioxirane Solvents: Acetone,Dichloromethane2.2 Reagents: Ammonia Solvents: Methanol
    标题:A New And Efficient Synthesis Of Cytidine And Adenosine Derivatives By Dimethyldioxirane Oxidation Of Thiopyrimidine And Thiopurine Nucleosides
    作者:Saladino,Raffaele; Et Al
    参考文献:Journal Of The Chemical Society 日期:1994 卷标:(21) 页码:3053-4]

    = 838-07-3
    反应条件:1.1 Reagents: Phosphorus Oxychloride,Sodium Azide Solvents: Acetonitrile2.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol
    标题:Novel Synthetic Route To 1-Substituted Cytosines
    作者:Ciszewski,Krzysztof; Et Al
    参考文献:Synthesis 日期:1995 卷标:(7) 页码:777-9]

    4449-32-5 = 838-07-3
    反应条件:1.1 Reagents: Tosyl Chloride,1-Methylpyrrolidine,Triethylamine1.2 Reagents: Ammonia Solvents: Water2.1 Reagents: Sodium Hydroxide Solvents: Water
    标题:Development Of New Amination Reaction At 4-Position Of Pyrimidine Nucleosides
    作者:Tsuchiya,Katsutoshi; Et Al
    参考文献:Nucleic Acids Research Supplement 日期:2002 卷标:2 页码:135-136]

    66-22-8 + 50-89-5 = 838-07-3
    反应条件:1.1 Catalysts: Nucleoside Deoxyribosyltransferase Solvents: Water; 2 H,Ph 6.5,40 °C2.1 Catalysts: Nucleoside Deoxyribosyltransferase Solvents: Water; 2 H,Ph 6.5,40 °C
    标题:Enzymatic Synthesis Of Nucleoside Analogues Using Immobilized 2'-Deoxyribosyltransferase From Lactobacillus Reuteri
    作者:Fernandez-Lucas,Jesus; Et Al
    参考文献:Applied Microbiology And Biotechnology 日期:2011 卷标:91(2) 页码:317-327]

    890-38-0 + 66-22-8 = 838-07-3
    反应条件:1.1 Catalysts: Nucleoside Deoxyribosyltransferase Solvents: Water; 2 H,Ph 6.5,40 °C2.1 Catalysts: Nucleoside Deoxyribosyltransferase Solvents: Water; 2 H,Ph 6.5,40 °C
    标题:Enzymatic Synthesis Of Nucleoside Analogues Using Immobilized 2'-Deoxyribosyltransferase From Lactobacillus Reuteri
    作者:Fernandez-Lucas,Jesus; Et Al
    参考文献:Applied Microbiology And Biotechnology 日期:2011 卷标:91(2) 页码:317-327]

    66-22-8 + 958-09-8 = 838-07-3
    反应条件:1.1 Catalysts: Nucleoside Deoxyribosyltransferase Solvents: Water; 2 H,Ph 6.5,40 °C2.1 Catalysts: Nucleoside Deoxyribosyltransferase Solvents: Water; 2 H,Ph 6.5,40 °C
    标题:Enzymatic Synthesis Of Nucleoside Analogues Using Immobilized 2'-Deoxyribosyltransferase From Lactobacillus Reuteri
    作者:Fernandez-Lucas,Jesus; Et Al
    参考文献:Applied Microbiology And Biotechnology 日期:2011 卷标:91(2) 页码:317-327]

    73-24-5 + 50-89-5 = 838-07-3
    反应条件:1.1 Catalysts: Nucleoside Deoxyribosyltransferase Solvents: Water; 2 H,Ph 6.5,40 °C2.1 Catalysts: Nucleoside Deoxyribosyltransferase Solvents: Water; 2 H,Ph 6.5,40 °C3.1 Catalysts: Nucleoside Deoxyribosyltransferase Solvents: Water; 2 H,Ph 6.5,40 °C
    标题:Enzymatic Synthesis Of Nucleoside Analogues Using Immobilized 2'-Deoxyribosyltransferase From Lactobacillus Reuteri
    作者:Fernandez-Lucas,Jesus; Et Al
    参考文献:Applied Microbiology And Biotechnology 日期:2011 卷标:91(2) 页码:317-327]

    890-38-0 + 65-71-4 = 838-07-3
    反应条件:1.1 Catalysts: Nucleoside Deoxyribosyltransferase Solvents: Water; 2 H,Ph 6.5,40 °C2.1 Catalysts: Nucleoside Deoxyribosyltransferase Solvents: Water; 2 H,Ph 6.5,40 °C3.1 Catalysts: Nucleoside Deoxyribosyltransferase Solvents: Water; 2 H,Ph 6.5,40 °C
    标题:Enzymatic Synthesis Of Nucleoside Analogues Using Immobilized 2'-Deoxyribosyltransferase From Lactobacillus Reuteri
    作者:Fernandez-Lucas,Jesus; Et Al
    参考文献:Applied Microbiology And Biotechnology 日期:2011 卷标:91(2) 页码:317-327]

    65-71-4 + 958-09-8 = 838-07-3
    反应条件:1.1 Catalysts: Nucleoside Deoxyribosyltransferase Solvents: Water; 2 H,Ph 6.5,40 °C2.1 Catalysts: Nucleoside Deoxyribosyltransferase Solvents: Water; 2 H,Ph 6.5,40 °C3.1 Catalysts: Nucleoside Deoxyribosyltransferase Solvents: Water; 2 H,Ph 6.5,40 °C
    标题:Enzymatic Synthesis Of Nucleoside Analogues Using Immobilized 2'-Deoxyribosyltransferase From Lactobacillus Reuteri
    作者:Fernandez-Lucas,Jesus; Et Al
    参考文献:Applied Microbiology And Biotechnology 日期:2011 卷标:91(2) 页码:317-327]

    6979-97-1 = 838-07-3
    反应条件:1.1 Reagents: Phosphorus Oxychloride,Sodium Azide Solvents: Acetonitrile2.1 Reagents: Phosphorus Oxychloride,Sodium Azide Solvents: Acetonitrile3.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol
    标题:Novel Synthetic Route To 1-Substituted Cytosines
    作者:Ciszewski,Krzysztof; Et Al
    参考文献:Synthesis 日期:1995 卷标:(7) 页码:777-9
Beta-胸苷置于1,8-二氮杂双环[5.4.0]十一碳-7-烯,((3H-[1,2,3]Triazolo[4,5-B]Pyridin-3-yl)Oxy)Tri(Pyrrolidin-1-yl)Phosphonium Hexafluorophosphate(V),Ammonium Hydroxide体系中,用 N,N-二甲基甲酰胺 作为反应溶剂,化学反应 2.02H,以92%的收率获得产物5-甲基-2'-脱氧胞苷
参考文献:一种基于pyaop的高效c 4胺化方法,可直接访问氧化的5Me Dc衍生物
标题:一种基于pyaop的高效c 4胺化方法,可直接访问氧化的5Me Dc衍生物
摘要:在过去的十年中,合成的氧化的5-Me Dc核苷及其衍生物已成为表观遗传学研究的重要工具.常规和新近报道的bop方法对这些特定的氧化的5-Me Du底物的c 4胺化的低效率,促使我们系统地研究基于鎓盐的偶联剂的性质如何影响嘧啶核苷的c 4胺化和使我们得出以下发现:不同的鎓偶联剂导致形成独特的活化中间体,并且在活化和氨解步骤中pyaop比bop的效力要强得多.直接胺化,无需核糖保护,超快活化,耐水性这种基于pyaop的c 4胺化方法的优点是,N-亲核试剂以及各种氧化的5Me Dc衍生物的优异收率.
DOI:10.1016/j.Tet.2018.10.046

海关参考信息

专利信息


专利号:US-9884885-B2
优先权日:2009-05-18
标题:Synthesis of labile base protected-modified deoxy and modified ribo nucleosides, corresponding phosphoramidites and supports and their use in high purity oligonucleotide synthesis
发明人:SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P
权利人:SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P; CHEMGENES CORP
摘要:This invention relates to novel method of synthesis of RNA utilizing N-2-acetyl protected guanine as nucleoside base, nucleosides, succinates, phosphoramidites, corresponding solid supports that are suitable for oligo deoxy nucleosides and RNA oligonucleotide synthesis. Our discovery using N-acetyl protected guanine as nucleoside base protecting group, which is significantly faster base labile protecting group, yet significantly more stable than commonly utilized-2-isobutyryl guanosine is a novel approach to obtain highest purity oligonucleotides. This approach is designed to lead to very high purity and very clean oligonucleotide, after efficient removal of the protecting groups, including acetyl group from guanine and to produce high purity therapeutic grade DNA oligonucleotides, RNA oligonucleotides, diagnostic DNA, diagnostic RNA for microarray platform. The deprotection of acetyl protecting groups of the natural deoxy and ribonucleosides occurs under substantially reduced time in contact with mild deprotection conditions such as mild bases, secondary amines for removal of such groups under such conditions would allows synthesis of various DNA and RNA of highest purity for diagnostics and therapeutic application. This approach is designed to lead to high purity large scale therapeutic grade oligonucleotide chimeras which consist of fluoro sugar modification in conjunction with deoxy nucleosides, ribonucleosides, modified base and modified sugar nucleosides. This approach is further designed to use acetyl guanine protecting group when other bases are sensitive nucleoside, and for use in oligo peptide synthesis and for support bound oligo nucleotides.

专利号:US-8981076-B2
优先权日:2008-11-29
标 题 :Synthesis of N-FMOC protected deoxy nucleosides, ribo nucleosides, modified deoxy and ribo nucleosides, and phosphoramidites, and their use in oligonucleotide synthesis
发明人:SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P
权利人:SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P; CHEMGENES CORP
摘要:This invention relates to synthesis of novel -N-FMOC protected nucleosides, succinates, phosphoramidites, corresponding solid supports that are suitable for oligo deoxy nucleosides and RNA oligonucleotide synthesis. Our discovery using N-FMOC as nucleoside base protecting group, which is highly base labile protecting group is a novel approach to obtain highest purity oligonucleotides. This approach is designed to lead to very high purity and very clean oligonucleotide, after efficient removal of the protecting groups and to produce high purity therapeutic grade DNA oligonucleotides, RNA oligonucleotides, diagnostic DNA, diagnostic RNA for microarray platform. The deprotection of FMOC protecting groups of the natural deoxy and ribonucleosides occurs under very mild deprotection conditions such as mild bases, secondary and tertiary amines for removal of such groups under such conditions would allows synthesis of various DNA and RNA of highest purity for diagnostics and therapeutic application. This approach is further designed to use FMOC protecting group on various base sensitive nucleoside, and for use in oligo peptide synthesis and for support bound oligo nucleotides. DNA oligonucleotides containing 3′-end dA at the 3′-terminal will be produced using the FMOC-dA-supports would lead to much reduced M−1 deletion sequences, and thereby high purity.

专利号:US-10167308-B2
优先权日:2013-09-14
标题:Highly efficient synthesis of long RNA using reverse direction approach
发明人:SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P
权利人:CHEMGENES CORP
摘要:The present invention relates to novel process of reverse 5′→3′ directed synthesis of RNA oligomers in the range of about 100-mer to about 200-mer has been developed and disclosed. Using that method demonstrated high quality RNA synthesis with coupling efficiency approaching 99%.

专利号:US-9605261-B2
优先权日:2008-09-06
标 题:RNA synthesis—phosphoramidites for synthetic RNA in the reverse direction, and application in convenient introduction of ligands, chromophores and modifications of synthetic RNA at the 3′-end
发明人:SRIVASTAVA SURESH C; PANDEY DIVYA; BAJPAI SATYA P; SRIVASTAVA NAVEEN P
权利人:CHEMGENES CORP
摘要:The present invention relates to novel phosphoramidites, A-n-bz, C-n-bz, C-n-ac, G-n-ac and U are produced with an HPLC purity of greater than 98% and 31 P NMR purity greater than 99%. A novel process of reverse 5′→3′ directed synthesis of RNA oligomers has been developed and disclosed. Using that method demonstrated high quality RNA synthesis with coupling efficiency approaching 99%.

专利号:US-7339051-B2
优先权日:2003-04-28
标题 :Compositions and methods for the treatment of severe acute respiratory syndrome (SARS)
发明人:CROOKE STANLEY T; ECKER DAVID J; SAMPATH RANGARAJAN; FREIER SUSAN M; MASSIRE CHRISTIAN; HOFSTADLER STEVEN A; LOWERY KRISTIN SANNES; SWAYZE ERIC E; BAKER BRENDA F; BENNETT C FRANK
权利人:ISIS PHARMACEUTICALS INC
摘要:The present invention provides design and synthesis of oligomeric compounds and compositions that can be administered to reduce the activity of SARS virus in vivo or in vitro, to prevent or treat SARS virus-associated disease, to detect AARS virus, and to diagnose SARS virus-associated diseases.

专利号:US-8324149-B2
优先权日:2008-11-18
标 题:Encapsidation of heterologous entities into virus-like particles
发明人:BUNDY BRADLEY C; SWARTZ JAMES R; CHAN WEI
权利人:BUNDY BRADLEY C; SWARTZ JAMES R; CHAN WEI; UNIV LELAND STANFORD JUNIOR
摘要:Methods are provided for the utilization of bacterial cell-free extracts in the synthesis of high yields of virus like particles with encapsidated cargo.
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主要参考文献


1: Giel-Pietraszuk M, Insińska-Rak M, Golczak A, Sikorski M, Barciszewska M, Barciszewski J. Quantification of 5-methyl-2'-deoxycytidine in the DNA. Acta Biochim Pol. 2015;62(2):281-6. doi: 10.18388/abp.2015_988. Epub 2015 Jun 22. 44 ( Pt 5):870-2. doi: 10.1107/s0108270188000897.
60:177-82. doi: 10.1016/j.freeradbiomed.2013.01.010. Epub 2013 Jan 30.
4: Shilkin ES, Petrova DV, Poltorachenko VA, Boldinova EO, Zharkov DO, Makarova AV. [Template Properties of 5-Methyl-2'-Deoxycytidine and 5-Hydroxymethyl-2'-Deoxycytidine in Reactions with Human Translesion and Reparative DNA Polymerases]. Mol Biol (Mosk). 2021 Mar-Apr;55(2):305-311. Russian. doi: 10.31857/S0026898421020130. 4(4):367-72. doi: 10.4155/bio.11.335. 8(12):e84620. doi: 10.1371/journal.pone.0084620.

合成参考文献


参考文献:10.18632/aging.100023
摘要:Dimauro T, David G. Chromatin modifications: the driving force of senescence and aging Aging (Albany NY). 2009 Feb 13;1(2):182–90.
参考文献:10.18632/aging.100106
摘要:Pegoraro G, Misteli T. The central role of chromatin maintenance in aging. Aging (Albany NY). 2009 Dec 09;1(12):1017–22.
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