CAS: 2002-35-9; (2R,3S,5R)-2-(Hydroxymethyl)-5-(6-(Methylamino)-9H-Purin-9-yl)Tetrahydrofuran-3-Ol

该化合物是一种经修改的核糖衍生物,其中肋骨糖在2'位置上缺乏一个氢氧基,基在异环氨基氨基组中被甲基化,这种结构改变增强了其稳定性,防止酶降解与未经改良的核糖化物相比,使其对生物化学和药理学研究具有价值.腺素能在N6位置的甲基化影响基底覆盖相互作用,为核酸研究和抗宣讲寡核酸设计提供了潜在应用.它的独特特性也使它成为核糖酸模拟合成的有用中间体,用于研究酶机制或开发治疗剂,适合于在分子生物学和药用化学领域有节制的实验用途.

结构式图片

上下游产品

N-1-methyl-2'-deoxyribofuranosiladenine iodide trimethylsulphonium hydroxide 2'-deoxy-D-adenosine trimethylselenonium hydroxydeN-methyladenine 6-methyladenosine-3'-O-yl>(methoxy)morpholinophosphine2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N6-methyladenosine-3'-O-yl(methoxy)morpholinophosphine Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-methylamino-purin-9-yl)-tetrahydro-furan-3-yl ester methyl ester 2'-deoxy-D-adenosine

合成工艺路线路线简述

    2'-脱氧腺苷置于sodium Hydroxide体系中,用 N,N-二甲基甲酰胺 用作溶剂,化学反应 21.0H,反应生成N6-甲基-2'-脱氧腺苷
    参考文献:定量lc-Ms无法提供小鼠胚胎干细胞和组织基因组中m6 Da或m4 Dc的证据.
    标题:定量lc-Ms无法提供小鼠胚胎干细胞和组织基因组中m6 Da或m4 Dc的证据.
    摘要:直到最近,人们相信,高等生物的基因组除了包含四个典型的dna碱基外,还仅包含5-甲基-Dc(m 5 Dc)作为控制表观遗传过程的修饰碱基.近年来,随着在干细胞和脑组织的dna中发现5-羟甲基-Dc(hmdc),5-甲酰基-Dc(fdc)和5-羧基-Dc(cadc),这种观点发生了巨大变化.N 6-甲基脱氧腺苷(m 6 Da)是据报道存在于各种真核生物基因组中的最新碱基.该碱与n 4-甲基脱氧胞苷(m 4Dc),首先被报道是细菌基因组的组成部分.在这项工作中,我们通过使用新型超灵敏uHPLC-Ms方法研究了这些潜在表观遗传相关的dna碱基的水平和分布.我们进一步报告了m 5 Dc,Hmdc,Fdc和cadc的定量数据,但我们无法检测到从小鼠胚胎干细胞或脑和肝组织分离的dna中的m 4 Dc或m 6 Da.表观遗传相关性.
    Doi:10.1002/anie.201700424

    海关参考信息

    专利信息


    专利号:US-2023295608-A1
    优先权日:2022-03-17
    标 题:Methods for Characterization of Viral Genome Using Base Modifications
    发明人:DAVIS STEVEN; RICHARDSON JARED
    权利人:REGENERON PHARMA
    摘要:Methods for assaying a sample of viral particles comprising a single-stranded DNA genome for strand-specificity are disclosed. In embodiments, the methods include synthesis of a synthetic DNA strand complementary to the single-stranded DNA genome by incorporating a modified base to yield a labeled double-stranded DNA product, purification of the labeled double-stranded DNA product, sequencing of the purified double-stranded DNA product on a sequencer, and determining the specificity of the viral single-stranded DNA genome based on the detection of the modified base of the synthetic DNA strand.

    专利号:US-11505815-B2
    优先权日:2017-11-14
    标题 :Compositions and methods related to non-templated enzymatic nucleic acid synthesis
    发明人:CHEN MICHAEL C; MCINROY GORDON R
    权利人:NUCLERA NUCLEICS LTD
    摘要:The invention relates to the use of an amine masked moiety in a method of enzymatic nucleic acid synthesis. The invention also relates to said amine masked moieties per se and a process for preparing nucleotide triphosphates comprising said amine masked moieties.

    专利号:EP-1112281-B1
    优先权日:1998-09-08
    标 题:Pteridine nucleotide analogs
    发明人:HAWKINS MARY E; PFLEIDERER WOLFGANG; BALIS FRANK
    权利人:US GOV HEALTH & HUMAN SERV
    摘要:The invention provides pteridine nucleotides of formula (I) which are highly fluorescent and which can be used in the chemical synthesis of fluorescent oligonucleotide. The invention further provides for fluorescent oligonucleotide comprising one or more pteridine nucleotides. In addition the invention provides for pteridine nucleotide triphosphates which may be used as the constituent monomers in DNA amplification procedures. The pteridine nucleotides are more stable and possess higher quantum yields than structurally similar pteridine nucleotides.

    专利号:US-6716971-B1
    优先权日:1998-09-08
    标题:Pteridine nucleotide analogs
    发明人:HAWKINS MARY E; PFLEIDERER WOLFGANG; BALIS FRANK
    权利人:US HEALTH
    摘要:The invention provides pteridine nucleotides of formula (I) which are highly fluorescent and which can be used in the chemical synthesis of fluorescent oligonucleotide. The invention further provides for fluorescent oligonucleotide comprising one or more pteridine nucleotides. In addition the invention provides for pteridine nucleotide triphosphates which may be used as the constituent monomers in DNA amplification procedures. The pteridine nucleotides are more stable and possess higher quantum yields than structurally similar pteridine nucleotides.

    专利号:WO-2009138985-A2
    优先权日:2008-05-15
    标 题:Coupling agents for the synthesis of polypeptides and polynucleotides

    专利号:US-5612468-A
    优先权日:1994-05-18
    标题:Pteridine nucletide analogs as fluorescent DNA probes
    发明人:HAWKINS MARY E; PFLEIDERER WOLFGANG; DAVIS MICHAEL D; BALIS FRANK
    权利人:US HEALTH
    摘要:The invention provides novel pteridine nucleotides which are highly fluorescent under physiological conditions and which may be used in the chemical synthesis of fluorescent oligonucleotides. The invention further provides for fluorescent oligonucleotides comprising one or more pteridine nucleotides. In addition the invention provides for pteridine nucleotide triphosphates which may be used as the constituent monomers in DNA amplification procedures.
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    合成参考文献


    参考文献:10.1038/sj.bjp.0704674
    摘要:King BF. 2‐Chloro‐N6‐methyl‐(N)‐methanocarba‐2′‐deoxyadenosine‐3′,5′‐bisphosphate is a selective high affinity P2Y1 receptor antagonist: Commentary on Boyer et al. British J Pharmacology. 2002 Apr;135(8):1839–40. doi: 10.1038/sj.bjp.0704674.
    参考文献:10.1038/sj.bjp.0704673
    摘要:Boyer JL, Adams M, Ravi RG, Jacobson KA, Harden TK. 2‐Chloro N6‐methyl‐(N)‐methanocarba‐2′‐deoxyadenosine‐3′,5′‐bisphosphate is a selective high affinity P2Y1 receptor antagonist. British J Pharmacology. 2002 Apr;135(8):2004–10. doi: 10.1038/sj.bjp.0704673.
    参考文献:10.1016/j.pain.2011.04.016
    摘要:Yousuf A, Klinger F, Schicker K, Boehm S. Nucleotides control the excitability of sensory neurons via two P2Y receptors and a bifurcated signaling cascade. Pain. 2011 Aug;152(8):1899–908.
    参考文献:10.1038/sj.bjp.0704789
    摘要:Buvinic S, Briones R, Huidobro‐Toro JP. P2Y1 and P2Y2 receptors are coupled to the NO/cGMP pathway to vasodilate the rat arterial mesenteric bed. British J Pharmacology. 2002 Jul;136(6):847–56. doi: 10.1038/sj.bjp.0704789.
    参考文献:10.1016/j.bbrc.2003.12.132
    摘要:Charles M, Ravanat J, Adamski D, D’Orazi G, Cadet J, Favier A, Berger F, Wion D. N6-Methyldeoxyadenosine, a nucleoside commonly found in prokaryotes, induces C2C12 myogenic differentiation. Biochemical and Biophysical Research Communications. 2004 Feb;314(2):476–82. doi: 10.1016/j.bbrc.2003.12.132.
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