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Nucleosides. Part L. . Structure of lumazine N 1 ‐(2′‐deoxy‐ D ‐ribonucleosides) ( = 1‐(2′‐deoxy‐ D ‐ribofuranosyl)pteridine‐2,4(1 H ,3 H )‐diones): A revision of the anomeric configuration
Author(s) -
Cao Xiaodong,
Pfleiderer Wolfgang,
Rosemeyer Helmut,
Seela Frank,
Bannwarth Willi,
Schönholzer Peter
Publication year - 1992
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19920750427
Subject(s) - chemistry , anomer , deoxyribonucleosides , stereochemistry , glycosidic bond , nuclear magnetic resonance spectroscopy , geminal , organic chemistry , enzyme
The anomeric configuration of the glycosidic bond in lumazine N 1 ‐(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.