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在预定位点合成含有2'-脱氧-6-硫代鸟苷的寡核苷酸。

Synthesis of oligonucleotides containing 2'-deoxy-6-thioguanosine at a predetermined site.

作者信息

Christopherson M S, Broom A D

机构信息

Department of Medicinal Chemistry, College of Pharmacy, University of Utah, Salt Lake City 84112.

出版信息

Nucleic Acids Res. 1991 Oct 25;19(20):5719-24. doi: 10.1093/nar/19.20.5719.

DOI:10.1093/nar/19.20.5719
PMID:1945849
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC328981/
Abstract

A new approach has been devised for the synthesis of oligonucleotides containing 2'-deoxy-6-thioguanosine [d(s6G)]. The synthesis of oligonucleotides containing d(s6G) requires special protection and deprotection strategies to prevent the thione functionality from undergoing oxidation and hydrolysis. Previous attempted syntheses have neglected to address this problem. By using the cyanoethyl protecting group for the thione and phenoxyacetyl for the exocyclic amino group, it was possible to deprotect oligonucleotides with a mixture of sodium hydroxide and sodium hydrogen sulfide without any significant conversion of d(s6G) to deoxyguanosine. Application of this strategy will allow investigation of the structural as well as biological activity of d(s6G)-containing oligonucleotides.

摘要

一种用于合成含2'-脱氧-6-硫代鸟苷[d(s6G)]的寡核苷酸的新方法已经设计出来。含d(s6G)的寡核苷酸的合成需要特殊的保护和脱保护策略，以防止硫酮官能团发生氧化和水解。以前的合成尝试都没有解决这个问题。通过使用氰基乙基保护硫酮基团，苯氧乙酰保护环外氨基，可以用氢氧化钠和硫化氢的混合物对寡核苷酸进行脱保护，而不会使d(s6G)显著转化为脱氧鸟苷。应用该策略将有助于研究含d(s6G)的寡核苷酸的结构和生物活性。

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Further studies on the mechanism of action of 6-thioguanine.6-硫鸟嘌呤作用机制的进一步研究。
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Double-stranded polydeoxyribonucleotides containing 6-thiodeoxyguanosine and 6-thiodeoxyinosine. Poly(d(A-C)-d(T-s 6 G)),poly(d(A-s 6 G)-d(T-C)) and poly(d(A-C)-d(T-s 6 I)).含有6-硫代脱氧鸟苷和6-硫代脱氧肌苷的双链聚脱氧核糖核苷酸。聚（d（A-C）-d（T-s6G））、聚（d（A-s6G）-d（T-C））和聚（d（A-C）-d（T-s6I））
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