title: What are the consequences of freezing the anomeric effect in nucleosides?
abstract: 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.
authors.affiliation: 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
authors.forename: Victor E
authors.initials: VE
authors.lastname: Marquez
authors.forename: Guangyu
authors.initials: G
authors.lastname: Sun
authors.forename: Maqbool A
authors.initials: MA
authors.lastname: Siddiqui
authors.forename: Yi-Chien
authors.initials: YC
authors.lastname: Lee
authors.forename: Joseph J
authors.initials: JJ
authors.lastname: Barchi
authors.forename: Igor V
authors.initials: IV
authors.lastname: Filippov
authors.forename: Nicklaus A
authors.initials: NA
authors.lastname: Landsman
authors.forename: James A
authors.initials: JA
authors.lastname: Kelley
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D007700:Kinetics; D009705:Nucleosides / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D009705:Nucleosides; D010100:Oxygen