反向寡核苷酸的合成与杂交特性

Synthesis and hybridization properties of inverse oligonucleotides.

作者信息

Marangoni M, Van Aerschot A, Augustyns P, Rozenski J, Herdewijn P

机构信息

Laboratory of Medicinal Chemistry, Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, B-3000 Leuven, Belgium.

出版信息

Nucleic Acids Res. 1997 Aug 1;25(15):3034-41. doi: 10.1093/nar/25.15.3034.

DOI:10.1093/nar/25.15.3034

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC146838/

Abstract

The synthesis of adenine and thymine cyclopentylethyl nucleosides is presented. This novel constrained monomeric building block is very difficult to incorporate into oligonucleotides. It was introduced in 13mer oligodeoxynucleotide sequences at a single position using H-phosphonate chemistry. Phosphoramidite chemistry completely failed in this particular case. The H-phosphonate building blocks were obtained starting from the corresponding phosphoramidites. Stability of duplexes with RNA and DNA is significantly reduced.

摘要

本文介绍了腺嘌呤和胸腺嘧啶环戊基乙基核苷的合成。这种新型的受限单体结构单元很难掺入寡核苷酸中。利用H-膦酸酯化学方法，将其引入到13聚体寡脱氧核苷酸序列中的单个位置。在这种特殊情况下，亚磷酰胺化学方法完全失败。H-膦酸酯结构单元是从相应的亚磷酰胺开始获得的。与RNA和DNA形成的双链体的稳定性显著降低。

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本文引用的文献

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5-Nitroindole as an universal base analogue.5-硝基吲哚作为一种通用的碱基类似物。

Nucleic Acids Res. 1994 Oct 11;22(20):4039-43. doi: 10.1093/nar/22.20.4039.

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Hybridization specificity, enzymatic activity and biological (Ha-ras) activity of oligonucleotides containing 2,4-dideoxy-beta-D-erythro-hexopyranosyl nucleosides.含有2,4-二脱氧-β-D-赤式-己吡喃糖基核苷的寡核苷酸的杂交特异性、酶活性及生物学（Ha-ras）活性

Nucleic Acids Res. 1993 Oct 11;21(20):4670-6. doi: 10.1093/nar/21.20.4670.

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Free energy of imperfect nucleic acid helices. 3. Small internal loops resulting from mismatches.不完全核酸螺旋的自由能。3. 错配导致的小内部环。

J Mol Biol. 1973 Aug 5;78(2):301-19. doi: 10.1016/0022-2836(73)90118-6.

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5-Fluorodeoxyuridine as an alternative to the synthesis of mixed hybridization probes for the detection of specific gene sequences.5-氟脱氧尿苷作为合成用于检测特定基因序列的混合杂交探针的替代物。

Proc Natl Acad Sci U S A. 1988 Mar;85(6):1735-9. doi: 10.1073/pnas.85.6.1735.

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