Effect of an N-substituent in sulfonamide-bridged nucleic acid (SuNA) on hybridization ability and duplex structure

A sulfonamide-bridged nucleic acid without an N-substituent (SuNA[NH]) was successfully synthesized. A comparison of the SuNA[NMe]- and SuNA[NH]-modified oligonucleotides revealed that the duplex-forming abilities of the SuNA[NMe]-modified oligonucleotides with complementary DNA and RNA were higher...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2016-01, Vol.14 (27), p.6531-6538
Main Authors: Mitsuoka, Yasunori, Aoyama, Hiroshi, Kugimiya, Akira, Fujimura, Yuko, Yamamoto, Tsuyoshi, Waki, Reiko, Wada, Fumito, Tahara, Saori, Sawamura, Motoki, Noda, Mio, Hari, Yoshiyuki, Obika, Satoshi
Format: Article
Language:English
Subjects:
Base Sequence
DNA - chemistry
DNA - genetics
Models, Molecular
Nitrogen - chemistry
Nucleic Acid Conformation
Nucleic Acid Hybridization
RNA - chemistry
RNA - genetics
Sulfonamides - chemistry
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Summary:A sulfonamide-bridged nucleic acid without an N-substituent (SuNA[NH]) was successfully synthesized. A comparison of the SuNA[NMe]- and SuNA[NH]-modified oligonucleotides revealed that the duplex-forming abilities of the SuNA[NMe]-modified oligonucleotides with complementary DNA and RNA were higher than those of the SuNA[NH]-modified oligonucleotides. The crystal structures of DNA duplexes containing a SuNA[NR] revealed that the helical structures of the two duplexes and hydration patterns around the bridge moiety were different. These results provide insights into hydration patterns and rationale for the high RNA affinity of SuNA-modified oligonucleotides.
ISSN:1477-0520
1477-0539
DOI:10.1039/c6ob01051b