Pyrrolidine nucleotides conformationally constrained via hydrogen bonding

0429051 - ÚOCHB 2015 CZ eng C - Konferenční příspěvek (zahraniční konf.)
Pohl, Radek - Poštová Slavětínská, Lenka - Rejman, Dominik
Pyrrolidine nucleotides conformationally constrained via hydrogen bonding.
Chemistry of Nucleic Acid Components. 16th Symposium. Praha: Institute of Organic Chemistry and Biochemistry AS CR, v. v. i, 2014 - (Hocek, M.), s. 352-353. Collection Symposium Series, 14. ISBN 978-80-86241-50-0.
[Symposium on Chemistry of Nucleic Acid Components /16./. Český Krumlov (CZ), 08.06.2014-13.06.2014]
Grant CEP: GA ČR GA13-24880S
Institucionální podpora: RVO:61388963
Klíčová slova: pyrrolidine nucleotides * PMEA * hydrogen bond
Kód oboru RIV: CC - Organická chemie

Conformation of pyrroPME nucleotide analogues was studied by means of NMR at different pD values in D2O solutions. Surprisingly, two stable conformers were found at pD > 9 for both cis and trans configurations and their ratio depended on the acid-base properties of nucleobase attached to pyrrolidine ring. The results of conformational analysis suggest that the conformation of the pyrrolidine ring is locked via intramolecular hydrogen bond between negatively charged phosphonate oxygen atom and protonized pyrrolidine nitrogen.
Trvalý link: http://hdl.handle.net/11104/0234443