What are the consequences of freezing the anomeric effect in nucleosides?
The consequences of freezing the orientation of the oxygen's lone pair orbitals--which determines whether the anomeric effect is operative or not--were studied theoretically and experimentally in two oxobicyclo-[3.1.0]hexane nucleosides (1 and 2). The results showed significant differences in the properties of these molecules, which correlated with the magnitude of the n2 --> sigma * delocalization.
Marquez
Victor E
VE
Laboratory of Medicinal Chemistry, Center for Cancer Research, National Cancer Institute at Frederick, National Institutes of Health, Frederick, Maryland 21702, USA. marquezv@mail.nih.gov
Sun
Guangyu
G
Siddiqui
Maqbool A
MA
Lee
Yi-Chien
YC
Barchi
Joseph J
JJ
Filippov
Igor V
IV
Landsman
Nicklaus A
NA
Kelley
James A
JA
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D007700:Kinetics; D009705:Nucleosides / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; D009705:Nucleosides; D010100:Oxygen