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核苷酸类似物的聚合反应I:核苷5'-磷酰咪唑与2'-氨基-2'-脱氧尿苷的反应

Polymerization of nucleotide analogues I: reaction of nucleoside 5'-phosphorimidazolides with 2'-amino-2'-deoxyuridine.

作者信息

Lohrmann R, Orgel L E

出版信息

J Mol Evol. 1976 May 26;7(4):253-67. doi: 10.1007/BF01743625.

DOI:10.1007/BF01743625
PMID:933177
Abstract

2'-Amino-2'-deoxyuridine reacts efficiently with nucleoside 5'-phosphorimidazolides in aqueous solution. The dinucleoside monophosphate analogues were obtained in yields exceeding 80% under conditions in which little reaction occurs with the natural nucleosides. In a similar way, the 5'-phosphorimidazolide of 2'-amino-2'-deoxyuridine undergoes self-condensation in aqueous solution to give a complex mixture of oligomers. The phosphoramidate bond in the dinucleoside monophosphate analogues is stable for several days at room temperature and pH 7. The mechanisms of their hydrolysis under acidic and alkaline conditions are described.

摘要

2'-氨基-2'-脱氧尿苷在水溶液中能与核苷5'-磷酰咪唑发生高效反应。在与天然核苷几乎不发生反应的条件下,可获得产率超过80%的二核苷单磷酸类似物。同样,2'-氨基-2'-脱氧尿苷的5'-磷酰咪唑在水溶液中会发生自缩合反应,生成复杂的低聚物混合物。二核苷单磷酸类似物中的磷酰胺键在室温及pH 7条件下可稳定存在数天。文中描述了它们在酸性和碱性条件下的水解机制。

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1
Polymerization of nucleotide analogues I: reaction of nucleoside 5'-phosphorimidazolides with 2'-amino-2'-deoxyuridine.核苷酸类似物的聚合反应I:核苷5'-磷酰咪唑与2'-氨基-2'-脱氧尿苷的反应
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2
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Efficient and rapid template-directed nucleic acid copying using 2'-amino-2',3'-dideoxyribonucleoside-5'-phosphorimidazolide monomers.

本文引用的文献

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Studies on some interactions and reactions of oligonucleotides in aqueous solution.寡核苷酸在水溶液中的一些相互作用和反应的研究。
Biochemistry. 1966 Aug;5(8):2722-8. doi: 10.1021/bi00872a032.
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Improved separation of transfer RNA's on polychlorotrifuoroethylene-supported reversed-phase chromatography columns.在聚氯三氟乙烯支持的反相色谱柱上改进转运RNA的分离。
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Oligomerization of activated derivatives of 3'-amino-3'-deoxyguanosine on poly(C) and poly(dC) templates.3'-氨基-3'-脱氧鸟苷的活化衍生物在聚(C)和聚(dC)模板上的寡聚化。
Nucleic Acids Res. 1985 Apr 11;13(7):2469-84. doi: 10.1093/nar/13.7.2469.
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Heteropolynucleotides as templates for non-enzymatic polymerizations.作为非酶促聚合反应模板的杂多核苷酸。
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Formation of nucleoside 5'-phosphoramidates under potentially prebiological conditions.
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Template-directed reactions of aminonucleosides.氨基核苷的模板导向反应。
J Mol Evol. 1977 Aug 5;9(4):323-8. doi: 10.1007/BF01796094.
9
Studies of oligoadenylate formation on a poly (U) template.在聚(U)模板上形成寡腺苷酸的研究。
J Mol Evol. 1979 Mar 15;12(3):237-57. doi: 10.1007/BF01732341.
J Org Chem. 1971 Jan 29;36(2):250-4. doi: 10.1021/jo00801a002.
4
Phosphoramidate analogs of oligonucleotides.寡核苷酸的磷酰胺酯类似物。
J Org Chem. 1970 Nov;35(11):3800-3. doi: 10.1021/jo00836a048.