Molecular recognition of pyrimidine nucleobases by triplex DNA receptors

Bioorganic & Medicinal Chemistry Letters
Zixing ZhuangHaidong Huang

Abstract

Triplex DNA receptors are known for their strong and specific binding of a variety of purine ligands. However, not many studies have been reported on their binding of pyrimidine ligands. Here we used fluorophore-labeled DNA receptors to study these binding interactions. The results suggest that in general, cytosine binds more strongly than thymine and uracil, although the selectivity between two pyrimidine ligands can be tuned by changing the surrounding nucleobases of the DNA receptor. In contrast, binding of pyrimidine nucleosides is much weaker, possibly due to lack of the N1 hydrogen bonding donor.

References

Aug 30, 1990·Nature·A D Ellington, J W Szostak
Jan 17, 1995·Biochemistry·D E Huizenga, J W Szostak
Apr 6, 2006·Nucleic Acids Research·Angel A MartíNicholas J Turro
Jan 25, 2012·Chembiochem : a European Journal of Chemical Biology·Yuanfeng PangNorio Teramae
Mar 31, 2015·Chemical Communications : Chem Comm·Jianping Huang, Hengquan Yang

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