Novel sulfur-containing microbial metabolite of primaquine.

Antimicrobial Agents and Chemotherapy
C D HuffordA M Clark

Abstract

Microbial metabolism studies of the antimalarial drug primaquine, using Streptomyces roseochromogenus (ATCC 13400) have produced an N-acetylated metabolite and a methylene-linked dimeric product, both of which have been previously reported, and a novel sulfur-containing microbial metabolite. The structure of the metabolite as a sulfur-linked dimer was proposed on the basis of spectral and chemical data. The molecular formula C34H44N6O4S was established from field-desorption mass spectroscopy and analytical data. The 1H- and 13C-nuclear magnetic resonance spectral data firmly established that the novel metabolite was a symmetrically substituted dimer of primaquine N-acetate with a sulfur atom linking the two units at C-5. The metabolite has been shown to be a mixture of stereoisomers which can equilibrate in solution. This observation was confirmed by microbial synthesis of the metabolite from optically active primaquine.

References

Mar 1, 1984·Applied and Environmental Microbiology·A M ClarkJ D McChesney
Mar 1, 1984·Applied and Environmental Microbiology·A M ClarkJ D McChesney
Feb 1, 1981·Antimicrobial Agents and Chemotherapy·A M ClarkJ D McChesney
Jan 1, 1983·Journal of Pharmaceutical Sciences·C D HuffordJ D McChesney
May 16, 1983·Biochemical and Biophysical Research Communications·A J Varghese

❮ Previous
Next ❯

Citations

Aug 21, 2013·Parasitology·Alice S ButterworthKatharine R Trenholme
Sep 1, 1991·Medicinal Research Reviews·A M Clark, C D Hufford

❮ Previous
Next ❯

Related Concepts

Related Feeds

CRISPR Screens in Drug Resistance

CRISPR-Cas system enables the editing of genes to create or correct mutations. This feed focuses on the application of CRISPR-Cas system in high-throughput genome-wide screens to identify genes that may confer drug resistance.

Antimalarial Agents (ASM)

Antimalarial agents, also known as antimalarials, are designed to prevent or cure malaria. Discover the latest research on antimalarial agents here.

Antimalarial Agents

Antimalarial agents, also known as antimalarials, are designed to prevent or cure malaria. Discover the latest research on antimalarial agents here.

Related Papers

Transactions of the Royal Society of Tropical Medicine and Hygiene
D Morley
Tropical Medicine & International Health : TM & IH
P Chavalitshewinkoon-PetmitrP Wilairat
© 2021 Meta ULC. All rights reserved