Nucleophilic N1-->N3 rearrangement of 5'-O-trityl-O2,3'-cycloanhydrothymidine

X B Yang; K Misiura; W J Stec; M J Potrzebowski; S Kaźmierski; M Wieczorek; W R Majzner; G D Bujacz

doi:10.1080/15257770008045451

Nucleophilic N1-->N3 rearrangement of 5'-O-trityl-O2,3'-cycloanhydrothymidine

Nucleosides Nucleotides Nucleic Acids. 2000 Oct-Dec;19(10-12):1657-73. doi: 10.1080/15257770008045451.

Authors

X B Yang¹, K Misiura, W J Stec, M J Potrzebowski, S Kaźmierski, M Wieczorek, W R Majzner, G D Bujacz

Affiliation

¹ Polish Academy of Sciences, Centre of Molecular and Macromolecular Studies, Lódź.

PMID: 11200264
DOI: 10.1080/15257770008045451

Abstract

5'-O-Trityl-O2,3'-cycloanhydrothymidine (1) heated at 150 degrees C in the presence of O,O-diethyl phosphate or O,O-diethyl phosphorothioate anions undergoes rearrangement into N3-isomer (2); its structure was established by both advanced NMR methods and X-ray crystallographic studies. The most probable mechanism of 1-->2 rearrangement relies upon reversibility of glycosidic bond cleavage process.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Crystallography, X-Ray
Magnetic Resonance Spectroscopy
Nucleic Acid Conformation
Thymidine / analogs & derivatives
Thymidine / chemistry*

Substances

5'-O-trityl-O(2),3'-cycloanhydrothymidine
Thymidine