7-脱氮-2'-脱氧黄苷：寡核苷酸的核碱基保护和碱基配对

7-deaza-2'-deoxyxanthosine: nucleobase protection and base pairing of oligonucleotides.

作者信息

Shaikh Khalil I, Leonard Peter, Seela Frank

机构信息

Laboratorium für Organische und Bioorganische Chemie, Institute für Chemie, Universität Osnabrück, Osnabrück, Germany.

出版信息

Nucleosides Nucleotides Nucleic Acids. 2007;26(6-7):737-41. doi: 10.1080/15257770701490837.

DOI:10.1080/15257770701490837

Abstract

Oligonucleotides containing 7-deaza-2'-deoxyxanthosine (1) and 2'-deoxyxanthosine (2) were prepared. The 2-(4-nitrophenyl)ethyl group is applicable for 7-deazaxanthine protection that is removed with DBU by beta-elimination, while the deprotection of the allyl residue with Pd (0) catalyst failed. Contrarily, the allyl group was found to be an excellent protecting group for 2'-deoxyxanthosine (2). The base pairing of nucleosides 1 and 2 with the four canonical DNA constituents as well as with 3 within the 12-mer duplexes is studied.

摘要

制备了含有7-脱氮-2'-脱氧黄苷（1）和2'-脱氧黄苷（2）的寡核苷酸。2-（4-硝基苯基）乙基可用于7-脱氮黄嘌呤的保护，该保护基可通过β-消除反应被DBU除去，而用Pd（0）催化剂对烯丙基残基进行脱保护则失败。相反，发现烯丙基是2'-脱氧黄苷（2）的优良保护基。研究了核苷1和2与四种标准DNA成分以及与12聚体双链体中的3的碱基配对。

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