堆积
单体
寡核苷酸
取代基
化学
结晶学
立体化学
复式(建筑)
DNA
脱氧尿苷
核糖核酸
有机化学
聚合物
生物化学
基因
作者
Pawan Kumar,Mick Hornum,Lise Junker Nielsen,Gérald Enderlin,Nicolai Krog Andersen,Christophe Len,Gwénaëlle Hervé,Guillaume Sartori,Poul Nielsen
摘要
Three 5-modified 2′-deoxyuridine nucleosides were synthesized and incorporated into oligonucleotides and compared with the previously published 5-(1-phenyl-1,2,3-triazol-4-yl)-2′-deoxyuridine monomer W. The introduction of an aminomethyl group on the phenyl group led to monomer X, which was found to thermally stabilize a 9-mer DNA:RNA duplex, presumably through the partial neutralization of the negative charge of the backbone. By also taking advantage of the stacking interactions in the major groove of two or more of the monomer X, an extremely high thermal stability was obtained. A regioisomer of the phenyltriazole substituent, that is the 5-(4-phenyl-1,2,3-triazol-1-yl)-2′-deoxyuridine monomer Y, was found to destabilize the DNA:RNA duplex significantly, but stacking in the major groove compensated for this when two to four monomers were incorporated consecutively. Finally, the 5-phenyl-2′-deoxyuridine monomer Z was incorporated for comparison, and it was found to give a more neutral influence on duplex stability indicating less efficient stacking interactions. The duplexes were investigated by CD spectroscopy and MD simulations.
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