title: Resonance assignments of diastereotopic CH(2)  protons in the anomeric side chain of selenoglycosides by means of (2) J(Se,H) spin-spin coupling constants.
abstract: Unambiguous resonance assignments of diastereotopic CH(2) protons in the anomeric side chain of nine alkyl- and aralkylselenoglycosides have been carried out on the basis of experimental CPMG-HSQMBC measurements and theoretical second order polarization propagator approach (SOPPA) calculations of geminal (77) Se-(1) H spin-spin coupling constants involving diastereotopic pro-R and pro-S protons. Theoretical conformational analyses have been performed at the MP2/6-311G** level. The conformational space of each of the selenoglycosides under study could be adequately described as a mixture of six interconverting conformers with the molar fractions depending on the nature of the side chain substituent at the selenium atom. The good agreement observed between measured and the weighted conformational averaged values of the calculated coupling constants provides a basis for reliable diastereotopic assignments in this type of carbohydrate structures.
authors.affiliation: A.E. Favorsky Irkutsk Institute of Chemistry, Russian Academy of Sciences, Irkutsk, Russia.
authors.forename: Yury Yu
authors.initials: YY
authors.lastname: Rusakov
authors.forename: Leonid B
authors.initials: LB
authors.lastname: Krivdin
authors.forename: Ambati Ashok
authors.initials: AA
authors.lastname: Kumar
authors.forename: László
authors.initials: L
authors.lastname: Szilágyi
authors.forename: Katalin E
authors.initials: KE
authors.lastname: Kövér
mesh_terms: D002236:Carbohydrate Conformation; D009682:Magnetic Resonance Spectroscopy / Q000379:methods* / Q000592:standards; D016566:Organoselenium Compounds / Q000737:chemistry*; D011522:Protons; D011789:Quantum Theory; D012015:Reference Standards; D013237:Stereoisomerism
chemical_list: D016566:Organoselenium Compounds; D011522:Protons