Recueil des Travaux Chimiques des Pays-Bas p. 343 - 346 (1988)
Update date:2022-08-02
Topics:
Koole, L. H.
Moody, H. M.
Buck, H. M.
Grouiller, A.
Essadiq, H.
et al.
The preparation and high-resolution 1H NMR conformational analysis of the two novel nucleoside analogues, 1-(3'-C-methyl-2'-deoxy-β-D-xylofuranosyl)uracil (compound 1) and 9-(3'-C-methyl-2'-deoxy-β-D-xylofuranosyl)adenine (compound 2), are described.Compounds 1 and 2show a pronounced preference for the north conformation of the sugar ring.The north conformation corresponds with a sterically favoured equatorial location of the methyl group.The C4'-C5' conformation in 1 and 2 is predominantly γt (trans orientation of O5' and C3').The configuration at C3' in 1 and 2 was corroborated via a one-dimensional NOE experiment.The structure of compound 1 (originally assigned as having the C3'-methyl group on the β-face of the furanosyl moiety) is revised on the basis of these data.
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Doi:10.1016/S0040-4039(00)82029-8
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