We describe the preparation and fluorescence properties of a set of new nucleosides in which a known hydrocarbon or oligothiophene fluorophore replaces the DNA base at C(1) of the deoxyribose moiety (see 3a - f). These compounds are potentially useful as probes in the study of the structure and dynamics of nucleic acids and their complexes with proteins. In addition, they may find use as fluorescent labels for nucleic-acid-based biomedical diagnostics methods. The fluorophores conjugated to deoxyribose at C(1) in the α-d-form include terphenyl, stilbene, terthiophene, benzoterthiophene, and pyrene. Also included is a non-fluorescent spacer in which cyclohexene replaces the DNA base. The nucleosides are derived from brominated fluorophore precursors and Hoffer's 2-deoxy-3,5-di-O-(p-toluoyl)-d-ribofuranosyl chloride. The emission maxima of the free nucleosides range from 345 to 536 nm. Also described are the 5'-(dimethoxytrityl) 3'-O-phosphoramidite derivatives 5a - f, suitable for incorporation into oligonucleotides by automated synthesizers.

中文翻译：

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用荧光团取代 DNA 碱基的新型核苷类似物。


我们描述了一组新核苷的制备和荧光特性，其中已知的碳氢化合物或寡噻吩荧光团取代了脱氧核糖部分 C(1) 处的 DNA 碱基（参见 3a - f）。这些化合物可用作研究核酸及其与蛋白质复合物的结构和动力学的探针。此外，它们还可以用作基于核酸的生物医学诊断方法的荧光标记。 α-d-形式的 C(1) 处与脱氧核糖缀合的荧光团包括三联苯、二苯乙烯、三联噻吩、苯并三联噻吩和芘。还包括非荧光间隔基，其中环己烯取代了 DNA 碱基。核苷源自溴化荧光团前体和 Hoffer's 2-脱氧-3,5-二-O-(对甲苯甲酰基)-d-呋喃核糖基氯。游离核苷的发射最大值范围为 345 至 536 nm。还描述了5'-(二甲氧基三苯甲基)3'-O-亚磷酰胺衍生物5a-f，其适合通过自动合成仪掺入寡核苷酸中。