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4-三唑并嘧啶酮核苷酸的合成及其在含5-甲基胞嘧啶的寡脱氧核糖核苷酸合成中的应用。

Synthesis of 4-triazolopyrimidinone nucleotide and its application in synthesis of 5-methylcytosine-containing oligodeoxyribonucleotides.

作者信息

Sung W L

出版信息

Nucleic Acids Res. 1981 Nov 25;9(22):6139-51. doi: 10.1093/nar/9.22.6139.

DOI:10.1093/nar/9.22.6139
PMID:7312633
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC327590/
Abstract

5'-0-Dimethoxytritylthymidine (2) was phosphorylated and base-modified simultaneously to yield the 4-triazolopyrimidinone nucleotide (3). Coupling between (3) and other common deoxyribonucleotides gave a fully protected nonamer (4). Deblocking under different conditions yielded the nonamer as phosphodiester with concomitant conversion of 4-triazolopyrimidinone to 5-methylcytosine (aqueous ammonia) or thymine (N1,N1,N3,N3-tetramethyl-guanidinium syn-4-nitrobenzaldoximate solution).

摘要

5'-O-二甲氧基三苯甲基胸苷（2）同时进行磷酸化和碱基修饰，生成4-三唑并嘧啶酮核苷酸（3）。（3）与其他常见脱氧核糖核苷酸之间的偶联反应得到了一个完全保护的九聚体（4）。在不同条件下脱保护，得到了作为磷酸二酯的九聚体，同时4-三唑并嘧啶酮转化为5-甲基胞嘧啶（氨水）或胸腺嘧啶（N1,N1,N3,N3-四甲基胍基顺式-4-硝基苯甲醛肟溶液）。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0834/327590/4f1e53af588a/nar00415-0295-a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0834/327590/4f1e53af588a/nar00415-0295-a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0834/327590/4f1e53af588a/nar00415-0295-a.jpg

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1
Synthesis of 4-triazolopyrimidinone nucleotide and its application in synthesis of 5-methylcytosine-containing oligodeoxyribonucleotides.4-三唑并嘧啶酮核苷酸的合成及其在含5-甲基胞嘧啶的寡脱氧核糖核苷酸合成中的应用。
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