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己糖核苷类似物掺入寡核苷酸:合成、碱基配对特性及酶稳定性

Incorporation of hexose nucleoside analogues into oligonucleotides: synthesis, base-pairing properties and enzymatic stability.

作者信息

Augustyns K, Vandendriessche F, Van Aerschot A, Busson R, Urbanke C, Herdewijn P

机构信息

Laboratory of Pharmaceutical Chemistry, Rega Institute for Medical Research, Leuven.

出版信息

Nucleic Acids Res. 1992 Sep 25;20(18):4711-6. doi: 10.1093/nar/20.18.4711.

Abstract

Oligonucleotides containing 1-(2,4-dideoxy-beta-D-erythro-hexopyranosyl)thymine (2) and 1-(3,4-dideoxy-beta-D-erythro-hexopyranosyl)thymine (3) were synthesized on a solid support using the phosphoramidite approach. The properties of these oligonucleotides were compared with the earlier reported characteristics of oligonucleotides containing 1-(2,3-dideoxy-beta-D-erythro-hexopyranosyl) thymine (1). The order in enzymatic stability of end-substituted oligonucleotides is 3 greater than 1 much greater than 2. The hybridization properties of the modified oligonucleotides are in reverse order: 2 much greater than 1 greater than 3.

摘要

采用亚磷酰胺法在固相载体上合成了含有1-(2,4-二脱氧-β-D-赤藓糖己吡喃糖基)胸腺嘧啶(2)和1-(3,4-二脱氧-β-D-赤藓糖己吡喃糖基)胸腺嘧啶(3)的寡核苷酸。将这些寡核苷酸的性质与早期报道的含有1-(2,3-二脱氧-β-D-赤藓糖己吡喃糖基)胸腺嘧啶(1)的寡核苷酸的特征进行了比较。末端取代寡核苷酸的酶稳定性顺序为3大于1远大于2。修饰寡核苷酸的杂交性质顺序相反:2远大于1大于3。

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