CAS: 3608-58-0; 2-Amino-9-((2R,3R,5S)-3-Hydroxy-5-(Hydroxymethyl)Tetrahydrofuran-2-yl)-1H-Purin-6(9H)-One

该化合物是核酸结构中具有关键作用的核糖,由配在脱氧核糖的纯碱基瓜宁组成,缺乏三度位置的氢氧基甘油组,使其与普通guanosine不同.这种修改使3'-deoxyguanosine成为DNA合成的重要建筑块,特别是在某些抗病毒和抗癌疗法方面.复合物在表面上一般为白色,在水中可溶于白,便于其在生物化学应用中使用.其分子式为C10H13N5O3,分子式反映碳,氢,氮和氧原子组成的分子重量.3'deoxyguanosine 也参与了各种生物化学途径,包括DNA的复制和修复,并且可以磷化成3'deoxyguanosine rimatis 3'-deguano dicroital,这是DNA聚合性研究的一个必要主题.其独特的结构特征和生物意义是生物生物学.

结构式图片

上下游产品

CAS号3608-57-9 (2R,3R,5S)-2-(2... | CAS号118-00-3 鸟苷 | CAS号1055407-32-3 N2-[(dimethylam... | CAS号1053251-34-5 O-((2R,3R,4R,5R... | CAS号7057-33-2 3'-脱氧胞苷 | CAS号1904-98-9 2,6-二氨基嘌呤 | CAS号34097-37-5 N,N-1H-嘌呤-2,6-二双乙酰胺 | CAS号112233-74-6 n2-acetyl-o6-(d... | CAS号90580-88-4 β-D-erythro-Pen... | CAS号157025-66-6 N-[9-[(2R,3R,5S... | CAS号869355-04-4 n2-(dimethylami...

合成工艺路线路线简述

  • 合成目标产物 3'-Deoxyguanosine 主要起始原料 2,6-Diaminopurine
  • (文献来源)合成步骤主要原料 2,6-Diaminopurine
鸟苷置于吡啶,咪唑,Ammonium Hydroxide,偶氮二异丁腈,四丁基氟化铵,三正丁基氢锡,溶剂黄146体系中,用 四氢呋喃,甲醇,N,N-二甲基甲酰胺,甲苯 作为反应溶剂,化学反应 262.5H,反应生成 3-脱氧鸟苷
参考文献:Preparation Of 2'-O-(.Beta.-Cyanoethyl Phosphoramidites) Of 3'-Deoxycytidine And 3'-Deoxyguanosine And Their Use For Solid-Phase Synthesis Of Oligodeoxynucleotides Containing 2',5'-Phosphodiester Linkages
标题:Preparation Of 2'-O-(.Beta.-Cyanoethyl Phosphoramidites) Of 3'-Deoxycytidine And 3'-Deoxyguanosine And Their Use For Solid-Phase Synthesis Of Oligodeoxynucleotides Containing 2',5'-Phosphodiester Linkages
摘要:Convenient,Preparative Scale Synthetic Routes To 2'-O-(Beta-Cyanoethyl N,N-Diisopropylphosphoramidites) Of 3'-Deoxycytidine (1) And 3'-Deoxyguanosine (2) Are Described. The 3'-Deoxycytidine Nucleoside 5 Was Constructed By A Modified Hilbert-Johnson Reaction In Which N-(4-Isobutyryl)-Cytosine (4) Was Ribosylated With Anomeric Acetate 3. Nucleoside 5 Was Converted To 5'-O(Dimethoxytrityl)-4-N-Isobutyryl-3'-Deoxycytidine (7) And Phosphitylated To Provide Phosphoramidite 1. Access To Derivatives Of 3'-Deoxyguanosine Was Provided By Selective Removal Of The 3'-Hydroxyl Of Guanosine (10). Thus,The 3'-O-Thiocarbamate Of 5'-O-(Dimethoxytrityl)-2-N-(Dimethylformamidyl)-2'-O-(Triisopropylsilyl)Guanosine (12) Was Reduced With Tributyltin Hydride And Converted To Phosphoramidite 2. In Results To Be Reported Elsewhere,Phosphoramidites 1 And 2 Were Used To Prepare Oligodeoxynucleotides Containing Novel 2',5'-Phosphodiester Linkages Using Automated Solid-Phase Dna Synthesis Methods With Average Stepwise Coupling Yields Of >97%.
DOI:10.1021/jo00103A014

海关参考信息

专利信息


专利号:US-11858953-B2
优先权日:2018-04-04
标 题:Compositions and methods for synthesis of phosphorylated molecules
发明人:CHAPUT JOHN; LIAO JEN-YU; BALA SAIKAT
权利人:UNIV CALIFORNIA
摘要:The invention provides compositions and methods for synthesis of phosphorylated organic compounds, including nucleoside triphosphates.

专利号:US-2007065922-A1
优先权日:2005-09-21
标题 :Biocatalytic synthesis of aminodeoxy purine N9-beta-D-nucleosides containing 3-amino-3-deoxy-beta-D-ribofuranose, 3-amino-2,3-dideoxy-beta-D-ribofuranose, and 2-amino-2-deoxy-beta-D-ribofuranose as sugar moieties
发明人:BARAI VLADIMIR N; EROSHEVSKAYA LUDMILLA A; MIKHAILOPULO IGOR A; AZHAYEV ALEX V; LAPINJOKI SEPPO P
权利人:METKINEN OY
摘要:Purine N 9 -β-D-nucleosides containing 3-amino-3-deoxy-β-D-ribofaranose, 3-amino-2,3-dideoxy-β-D-ribofuranose, and 2-amino-2-deoxy-β-D-ribofuranose as sugar moieties are synthesized by biocatalytic transglycosylation of purine bases and the respective 3′-amino-3′-deoxyuridine, 3′-amino-3′-deoxythymidine and 2′-amino-2′-deoxyuridine as donors of the carbohydrate moiety, and the cells of Escherichia coli as a biocatalyst or glutaraldehyde (GA) treated cells of Escherichia coli as a biocatalyst or a mixture of thymidine (uridine) phosphorylase and purine nucleoside phosphorylase.

专利号:US-8614312-B2
优先权日:2008-02-21
标 题 :Method for preparing nucleotides and related analogues by synthesis on soluble substrate, and biological tools thus prepared
发明人:PEYROTTES SUZANNE; PERIGAUD CHRISTIAN; CRAUSTE CELINE
权利人:PEYROTTES SUZANNE; PERIGAUD CHRISTIAN; CRAUSTE CELINE; CENTRE NAT RECH SCIENT; UNIV MONTPELLIER II
摘要:The invention concerns a method for preparing monomer nucleotides or nucleotide analogues comprising the steps of: (1) coupling a soluble polyethylene glycol support provided with at least one diacid or ether-acid linker and a monomer nucleoside or nucleoside analogue to an amine group or hydroxyl group of the nucleoside with the aid of a coupling agent; (2) at least one step for phosphorylation of said nucleoside or nucleoside analogue coupled to said support with a phosphorylation agent; (3) cleavage of said support and recovery of at least one monomer nucleotide or nucleotide analogue. The nucleotides prepared are biological tools.

专利号:US-2004181078-A1
优先权日:1997-10-10
标 题 :Tetraphosphonate bicyclic trisanhydrides
发明人:PANKIEWICZ KRZYSZTOF W; LESIAK KRYSTYNA; WATANABE KYOICHI A
权利人:PHARMASSET LTD
摘要:Disclosed are novel bicyclic tris(anhydride)s useful as intermediates in the synthesis of biologically active compounds, and the compounds which may be synthesized from such intermediates.

专利号:US-2020239500-A1
优先权日:2018-04-04
标 题 :Compositions and Methods for Synthesis of Phosphorylated Molecules

专利号:US-2024002331-A1
优先权日:2022-06-08
标 题 :Ionizable cationic lipids and lipid nanoparticles, and methods of synthesis and use thereof
发明人:ALI MIR; BOESCH AUSTIN WAYNE; DRUMMOND DARYL CLARK; KUHLMAN WILLIAM; NIELSEN ULRIK
权利人:TIDAL THERAPEUTICS INC
摘要:Provided are ionizable cationic lipids and lipid nanoparticles for the delivery of nucleic acids to cells (e.g., immune cells), and methods of making and using such lipids and targeted lipid nanoparticles.
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合成参考文献


参考文献:10.1016/0166-3542(86)90030-6
摘要:Widell A, Hansson BG, Oberg B, Nordenfelt E. Influence of twenty potentially antiviral substances on in vitro multiplication of hepatitis A virus. Antiviral Res. 1986 Mar;6(2):103–12. doi: 10.1016/0166-3542(86)90030-6.
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