N.m.r. studies of the flexibility of the glycosyl ring in thymidine and uridine nucleosides.
1H-N.m.r. spectroscopy at various temperatures has been used to investigate the flexibility of the glycosyl ring and to calculate the percentage of N- and S-character in the most favoured conformations in solution adopted by various pyrimidine deoxyribonucleosides. The position and orientation of substituents have a definite and predictable influence on the conformation of the deoxyribose ring in these nucleosides. The deoxyribose rings in the nucleosides studied were, in general, flexible except for those of 3'-deoxy-3'-fluoro- and 3'-azido-3'-deoxy-thymidine and 2'-deoxy-2'-fluoro-5-methyl-arabinosyluracil.
Hicks
N
N
Chemistry Department, Warwick University, Great Britain.
Howarth
O W
OW
Hutchinson
D W
DW
D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010430:Pentosyltransferases / Q000378:metabolism; D013816:Thermodynamics; D013936:Thymidine / Q000737:chemistry* / Q000378:metabolism; D014529:Uridine / Q000737:chemistry* / Q000378:metabolism
D010430:Pentosyltransferases; C021888:nucleoside deoxyribosyltransferase; D013936:Thymidine; D014529:Uridine