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...

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Published inJournal of antibiotics Vol. 50; no. 10; pp. 866 - 873
Main Authors SZTARICSKAI, FERENC, DINYA, ZOLTÁN, BATTA, GYULA, MOCSÁRI, ANIKÓ, HOLLÓSI, MIKLÓS, MAJER, ZSUZSA, MASUMA, ROKURO, OMURA, SATOSHI
Format Journal Article
LanguageEnglish
Published TOKYO JAPAN ANTIBIOTICS RESEARCH ASSOCIATION 1997
Japan Antibiotics Research Assoc
Japan Antibiotics Research Association
Subjects
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Bacteria - drug effects
Biological and medical sciences
Biotechnology & Applied Microbiology
Clindamycin - chemistry
Immunology
Life Sciences & Biomedicine
Lincomycin - analogs & derivatives
Lincomycin - chemical synthesis
Lincomycin - chemistry
Lincomycin - pharmacology
Magnetic Resonance Spectroscopy
Medical sciences
Microbial Sensitivity Tests
Microbiology
Molecular Structure
Oxidation-Reduction
Pharmacology & Pharmacy
Pharmacology. Drug treatments
Science & Technology
Sulfones - chemical synthesis
Sulfones - chemistry
Sulfones - pharmacology
Sulfoxides - chemical synthesis
Sulfoxides - chemistry
Sulfoxides - pharmacology
OLIGOSACCHARIDE
Sulfone
Clindamycin
FAB mass spectrum
In vitro
Modeling
Biological activity
Chemical modification
Lincomycin
Aminoglycoside
Analog
Sulfoxide
Ethylene oxide
Oxidation
Antibacterial agent
Chemical synthesis
Physicochemical properties
Structural analysis
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Summary: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.
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ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.50.866