Emergence of bacterial resistance has eroded the effectiveness of many life saving antibiotics leading to an urgent need for new chemical classes of antibacterial agents. We have applied a Staphylococcus aureus fitness test strategy to natural products screening to meet this challenge. In this paper we report the discovery of kibdelomycin A, a demethylated congener of kibdelomycin, the representative of a novel class of antibiotics produced by a new strain of Kibdelosporangium. Kibdelomycin A is a potent inhibitor of DNA gyrase and topoisomerase IV, inhibits DNA synthesis and shows whole cell antibiotic activity, albeit, less potently than kibdelomycin. Kibdelomycin C-33 acetate and tetrahydro-bisdechloro derivatives of kibdelomycin were prepared which helped define a basic SAR of the family.
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http://dx.doi.org/10.1016/j.bmcl.2012.09.071 | DOI Listing |
Angew Chem Int Ed Engl
September 2024
National Institute of Biological Sciences, Beijing, 7 Science Park Road ZGC Life Science Park, Beijing, 102206, P.R. China.
Kibdelomycin (KBD) and amycolamicin (AMM) are potent natural antibiotics effective against antibiotic-resistant Gram-positive pathogens, including vancomycin-intermediate Staphylococcus aureus (S. aureus, VISA), methicillin-resistant S. aureus (MRSA), and quinolone-resistant S.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
October 2024
Institut für Pharmazeutische Wissenschaften, Albert-Ludwigs-Universität Freiburg, Albertstrasse 25, 79104, Freiburg, Germany.
Many bacterial natural products contain C-branched sugars, including components from the outer cell wall or antibiotically active metabolites. The enzymatic C-branching of keto sugars leading to longer side chains (≥C) is catalyzed by thiamine diphosphate (ThDP)-dependent enzymes. Chiral tertiary α-hydroxy ketones are formed in this process.
View Article and Find Full Text PDFChem Sci
March 2023
Organic chemistry laboratory, University of Bayreuth Universitaetsstr. 30 95447 Bayreuth Germany
A convergent total synthesis of bacterial gyrase B/topoisomerase IV inhibitor kibdelomycin (a.k.a.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
August 2022
Department of Chemistry, Scripps Research, 10550N. Torrey Pines Road, La Jolla, CA 92122, USA.
A modular total synthesis of kibdelomycin is disclosed that should enable structure-activity relationship (SAR) studies of this interesting class of antibiotics. The route uses simple building blocks and addresses lingering questions about its structural assignment and relationship to amycolamicin, a recently described natural product reported to have a similar structure. Initial antibacterial assays reveal that both C-22 epimers (the N-glycosidic linkage) of the natural product have similar activity while structurally truncated analogs lose activity.
View Article and Find Full Text PDFBiotechnol Rep (Amst)
June 2022
Institution of Excellence, Vijnana Bhavan, University of Mysore, Manasagangotri, Mysore 570006, India.
The microorganisms that have developed resistance to available therapeutic agents are threatening the globe and multidrug resistance among the bacterial pathogens is becoming a major concern of public health worldwide. Bacteria develop protective mechanisms to counteract the deleterious effects of antibiotics, which may eventually result in loss of growth-inhibitory potential of antibiotics. ESKAPE ( and spp.
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