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Acyclic purine nucleoside analogues : computational and NMR studies of conformational behaviour

The conformational space of N-7 and N-9-(2-hydroxypropyl)-6-(N-pyrrolyl)purine as well as of N-7 and N-9-(2,3-dihydroxypropyl)-6-(N-pyrrolyl)purine has been studied by molecular mechanics (MMX force field) and semiempirical (PM3) calculations. Eight local minima were obtained for the N-7-(2-hydroxypropyl) regioisomer by the MMX force field and reoptimised by the PM3 method to locate the global minimum. The conformation of the N-7-(2,3-dihydroxypropyl) regioisomer is locked by intramolecular H-bonding and therefore more rigid. The results of theoretical calculations are in agreement with 1H and 13C NMR analysis of substituent chemical shifts, C-H and H-H coupling constants and connectivities in 2D homo- and heteronuclear correlation spectra

acyclic purine nucleoside analogues; conformation; MMX; PM3; 1H and 13C NMR spectroscopy

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