Chemical synthesis and structural study of lincomycin sulfoxides and a sulfone.
Oxidation of lincomycin with dimethyldioxirane resulted in the sulfoxide-glycosides 3a and 3b, whose treatment with osmium tetraoxide and N-methylmorpholine-N-oxide afforded the same sulfone; 4. According to FAB-MS and CD investigations, the absolute configuration of the sulfur atom in 3a and 3b is R and S, respectively. The new, unsaturated antibiotic analog (6) derived from clindamycin exists in the 4C1 conformation. The antibiotic activities of the synthesized compounds were also studied.
Sztaricskai
F
F
Research Group of Antibiotics, Hungarian Academy of Sciences, L. Kossuth University, Debrecen, Hungary.
Dinya
Z
Z
Batta
G
G
Mocsári
A
A
Hollósi
M
M
Majer
Z
Z
Masuma
R
R
Omura
S
S
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D002981:Clindamycin / Q000737:chemistry; D008034:Lincomycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013450:Sulfones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013454:Sulfoxides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D013450:Sulfones; D013454:Sulfoxides; C109714:lincomycin sulfone; C109713:lincomycin sulfoxide; D002981:Clindamycin; D008034:Lincomycin