Synthesis of the liposidomycin diazepanone nucleoside.
[structure: see text] The synthesis of the liposidomycin degradation product 4 from D-glucose establishes its stereochemistry as 5'S,6'S and, by incorporation of the earlier diazepanone relative stereochemical assignment, establishes the absolute stereochemistry of the liposidomycins 1 and 2 as 5'S,6'S,2'''S,3'''S.
Knapp
Spencer
S
Department of Chemistry & Chemical Biology, Rutgers The State University of New Jersey, Piscataway, New Jersey 08854-8087, USA.
Morriello
Gregori J
GJ
Doss
George A
GA
D001381:Azepines / Q000138:chemical synthesis*; D003500:Cyclization; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D010458:Peptidyl Transferases / Q000037:antagonists & inhibitors*; D014498:Uracil / Q000031:analogs & derivatives / Q000138:chemical synthesis*
C451485:6'-(5-carboxy-1,4-dimethyl-3-oxo-2H,3H-1,4-diazepin-2-yl)uracil; D001381:Azepines; D004791:Enzyme Inhibitors; D014498:Uracil; D010458:Peptidyl Transferases