NUCLEOSIDES .50. STRUCTURE OF LUMAZINE N1-(2'-DEOXY-D-RIBONUCLEOSIDES) (= 1-(2'-DEOXY-D-RIBOFURANOSYL)PTERIDINE-2,4(1H,3H)-DIONES) - A REVISION OF THE ANOMERIC CONFIGURATION

Autor(en): CAO, XD
PFLEIDERER, W
ROSEMEYER, H 
SEELA, F
BANNWARTH, W
SCHONHOLZER, P
Stichwörter: Chemistry; Chemistry, Multidisciplinary; GENERAL SYNTHESIS; N-GLYCOSIDES
Erscheinungsdatum: 1992
Herausgeber: NEW SWISS CHEMICAL SOC
Journal: HELVETICA CHIMICA ACTA
Volumen: 75
Ausgabe: 4
Startseite: 1267
Seitenende: 1273
Zusammenfassung: 
The anomeric configuration of the glycosidic bond in lumazine N1-(2'-deoxy-D-ribonucleosides) 1-6 was investigated by NOE difference spectroscopy. The former configurational assignment of the alpha- and beta-D-anomers 1 and 2, 3 and 4, and 5 and 6, respectively, has to be reversed to be in agreement with the physical data. Additional proof is presented by X-ray analysis of 3 and 6. Chemical interconversions of 1-(2'-deoxy-beta-D-ribofuranosyl)-6,7-diphenyllumazine (6) into 2,3'-anhydrolumazine 2'-deoxyribonucleosides 16 and 17 are also in agreement with the revised anomeric configuration.
ISSN: 0018019X
DOI: 10.1002/hlca.19920750427

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