Chemical synthesis and structural study of lincomycin sulfoxides and a sulfone

F. Sztaricskai, Z. Dinya, G. Batta, Anikó Mocsári, M. Hollósi, Zs. Majer, Rokuro Masuma, Satoshi Omura

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)866-873
Number of pages8
JournalJournal of Antibiotics
Volume50
Issue number10
Publication statusPublished - Oct 1997

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Sulfones
sulfoxide
Anti-Bacterial Agents
Lincomycin
Osmium
Clindamycin
Glycosides
Sulfur
lincomycin sulfoxide
4-methylmorpholine N-oxide
dimethyldioxirane

ASJC Scopus subject areas

  • Pharmacology
  • Molecular Medicine

Cite this

Chemical synthesis and structural study of lincomycin sulfoxides and a sulfone. / Sztaricskai, F.; Dinya, Z.; Batta, G.; Mocsári, Anikó; Hollósi, M.; Majer, Zs.; Masuma, Rokuro; Omura, Satoshi.

In: Journal of Antibiotics, Vol. 50, No. 10, 10.1997, p. 866-873.

Research output: Contribution to journalArticle

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AU - Hollósi, M.

AU - Majer, Zs.

AU - Masuma, Rokuro

AU - Omura, Satoshi

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