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Publication Abstract from PubMed

Oligonucleotides modified with 2'- O,4'- C-spirocyclopropylene-bridged nucleic acid (scpBNA) exhibit excellent duplex-forming ability with their complementary single-stranded RNA (ssRNA). Here, we demonstrate that scpBNA bearing a 2-thiothymine (scpBNA-S(2)T) or 2-selenothymine (scpBNA-Se(2)T) nucleobase provides robust mismatch discrimination capabilities to oligonucleotides without compromising their high binding affinities toward the full complementary ssRNA. X-ray crystallographic analysis of a self-assembling oligonucleotide featuring 2',4'-BNA/LNA-2-thiothymine (2',4'-BNA/LNA-S(2)T, where 2',4'-BNA and LNA stand for "2'- O,4'- C-methylene-bridged nucleic acid" and "locked nucleic acid", respectively), a prototype of scpBNA-S(2)T, revealed that the 2-thiocarbonyl moiety plays a crucial role in the destabilization of thymine-guanine mismatched wobble base pairs.

Hybridization and Mismatch Discrimination Abilities of 2',4'-Bridged Nucleic Acids Bearing 2-Thiothymine or 2-Selenothymine Nucleobase.,Habuchi T, Yamaguchi T, Aoyama H, Horiba M, Ito KR, Obika S J Org Chem. 2019 Feb 1;84(3):1430-1439. doi: 10.1021/acs.joc.8b02863. Epub 2019, Jan 24. PMID:30632750^[1]

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.