Nucleosides. Part L.. 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 |
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| Authors: | Xiaodong Cao Wolfgang Pfleiderer Helmut Rosemeyer Frank Seela Willi Bannwarth Peter Schnholzer |
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| Institution: | Xiaodong Cao,Wolfgang Pfleiderer,Helmut Rosemeyer,Frank Seela,Willi Bannwarth,Peter Schönholzer |
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| Abstract: | 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 α - and β -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-β-D -ribofuranosyl)-6,7-diphenyllumazine ( 6 ) into 2,3′ -anhydrolumazine 2′-deoxyribonucleosides 16 and 17 are also in agreement with the revised anomeric configuration. |
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