CAS: 60966-26-9; 2'-Amino-2'-Deoxyguanosine

该化合物是guanosine的核核素类比,其特点是在脱氧核糖的2欧元位置上存在一个氨基组,这种改变会影响其生物活动和与核酸的相互作用,该化合物通常显示一种纯基结构,这是其在核酸合成和功能中的作用所必不可少的,在生理条件下水和表现出稳定性,使之与生物化学应用有关.氨基组可以参与氢结扎,这可能影响其与补充核糖核酸的结合. 2欧元-氨-2欧元-脱氧基氨基苯对与分子生物学有关的研究感兴趣,特别是涉及DNA合成,修复机制以及针对核酸过程的治疗剂研制的研究,其结构上的修改还可能使人们深入了解新药的设计或医学化学领域的探针.

结构式图片

相似化合物

118-00-3 38819-10-2 26578-09-6

上下游产品

9-(2-amino-2-deoxy-β-D-ribofuranosyl)-2-chlorohypoxanthine 2-amino-6-hydroxypurine 1-(2-amino-2-deoxy-β-D-ribofuranosyl)uracil 2-Chloro-6-hydroxypurine

合成工艺路线路线简述

  • 合成目标产物 2'-Amino-2'-Deoxyguanosine 主要起始原料 2'-Amino-2'-Deoxy-5'-O-(4,4'-Dimethoxytrityl)Uridine
  • (文献来源)合成步骤主要原料 2'-Amino-2'-Deoxy-5'-O-(4,4'-Dimethoxytrityl)Uridine
5'-O-Dimethoxytrityl-2'-Amino-2'-Deoxyuridine置于n,O-双三甲硅基乙酰胺,正丁胺,三氯乙酸体系中,用 四氢呋喃,乙醇,乙腈 作为反应溶剂,化学反应 5.5H,反应生成 2'-氨基-2'-脱氧鸟苷
参考文献:改进了2'-氨基-2'-脱氧鸟苷及其亚磷酰胺的合成.
标题:改进了2'-氨基-2'-脱氧鸟苷及其亚磷酰胺的合成.
摘要:2'-氨基-2'-脱氧核苷和包含它们的寡核苷酸已被证明对一系列生化应用非常有效.鸟苷类似物及其亚磷酰胺衍生物先前已经通过转糖基化从2'-氨基-2'-脱氧尿苷中获得,但是总体效率和便利性有限.使用已知反应类型的简单修饰,我们已经开发了有用的方案,与以前报道的相比,具有更大的便利性,更少的步骤和更高的产率来获得2'-氨基-2'-脱氧鸟苷及其两个亚磷酰胺衍生物.这些亚磷酰胺为将2'-氨基-2'-脱氧鸟苷掺入寡核苷酸中提供了有效的合成子.
DOI:10.1016/j.Bmc.2005.08.050

海关参考信息

专利信息


专利号:US-4849513-A
优先权日:1983-12-20
标 题 :Deoxyribonucleoside phosphoramidites in which an aliphatic amino group is attached to the sugar ring and their use for the preparation of oligonucleotides containing aliphatic amino groups
发明人:SMITH LLOYD M; FUNG STEVEN; KAISER ROBERT J
权利人:CALIFORNIA INST OF TECHN
摘要:The invention consists of compounds and methods for the synthesis of oligonucleotides which contain one or more free aliphatic amino groups attached to the sugar moieties of the nucleoside subunits. The synthetic method is versatile and general, permitting amino groups to be selectively placed at any position on oligonucleotides of any composition or length which is attainable by current DNA synthetic methods. Fluorescent dyes or other detectable moieties may be covalently attached to the amino groups to yield the corresponding modified oligonucleotide.

专利号:US-5118802-A
优先权日:1983-12-20
标 题:DNA-reporter conjugates linked via the 2' or 5'-primary amino group of the 5'-terminal nucleoside
发明人:SMITH LLOYD M; FUNG STEVEN; KAISER JR ROBERT J
权利人:CALIFORNIA INST OF TECHN
摘要:The invention consists of compounds and methods for the synthesis of oligonucleotides which contain one or more free aliphatic amino groups attached to the sugar moieties of the nucleoside subunits. The synthetic method is versatile and general, permitting amino groups to be selectively placed at any position on oligonucleotides of any composition or length which is attainable by current DNA synthetic methods. Fluorescent dyes or other detectable moieties may be covalently attached to the amino groups to yield the corresponding modified oligonucleotide.

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-5118800-A
优先权日:1983-12-20
标 题 :Oligonucleotides possessing a primary amino group in the terminal nucleotide
发明人:SMITH LLOYD M; FUNG STEVEN; KAISER JR ROBERT J
权利人:CALIFORNIA INST OF TECHN
摘要:The invention consists of compounds and methods for the synthesis of oligonucleotides which contain one or more free aliphatic amino groups attached to the sugar moieties of the nucleoside subunits. The synthetic method is versatile and general, permitting amino groups to be selectively placed at any position on oligonucleotides of any composition or length which is attainable by current DNA synthetic methods. Fluorescent dyes or other detectable moieties may be covalently attached to the amino groups to yield the corresponding modified oligonucleotide.

专利号:US-5015733-A
优先权日:1983-12-20
标题 :Nucleosides possessing blocked aliphatic amino groups
发明人:SMITH LLOYD M; FUND STEVEN; KAISER JR ROBERT J
权利人:CALIFORNIA INST OF TECHN
摘要:The invention consists of compounds and methods for the synthesis of oligonucleotides which contain one or more free aliphatic amino groups attached to the sugar moieties of the nucleoside subunits. The synthetic method is versatile and general, permitting amino groups to be selectively placed at any position on oligonucleotides of any composition or length which is attainable by current DNA synthetic methods. Fluorescent dyes or other detectable moieites may be covalently attached to the amino groups to yield the corresponding modified oligonucleotide.

专利号:US-2005059817-A1
优先权日:2000-09-01
标题 :Methods for synthesizing nucleosides, nucleoside derivatives and non-nucleoside derivatives
发明人:BEIGELMAN LEONID; KARPEISKY ALEXANDER; SEREBRYANY VLADMIR; HAEBERLI PETER; SWEEDLER DAVID
权利人:SIRNA THERAPEUTICS INC
摘要:The present invention provides methods for the chemical synthesis of nucleosides and derivatives thereof, including 2′-amino, 2′-N-phthaloyl, 2′-O-methyl, 2′-0-silyl, 2′-O-triisopropylsilyloxymethyl, 2′-OH nucleosides, C-nucleosides, nucleoside phosphoramidites, C-nucleoside phosphoramidites, and non-nucleoside derivatives.
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合成参考文献


参考文献:10.1093/nar/25.3.648
摘要:Sjögren AS, Pettersson E, Sjöberg BM, Strömberg R. Metal ion interaction with cosubstrate in self-splicing of group I introns. Nucleic Acids Res. 1997 Feb 01;25(3):648–53.
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