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Updated: Mar 7, 2026

Synthesis of Masarimycin, a Small Molecule Inhibitor of Gram-Positive Bacterial Growth
Published on: January 7, 2022
Mimics of pramanicin derived from pyroglutamic acid and their antibacterial activity
Song Wei Benjamin Tan1, Christina L L Chai2, Mark G Moloney3
1Department of Chemistry, Chemistry Research Laboratory, The University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK. mark.moloney@chem.ox.ac.uk and Institute of Chemical and Engineering Sciences (ICES), 8 Biomedical Grove, Neuros Building, #07-01/02/03, Singapore 138665, Singapore. phacllc@nus.edu.sg.
Abstract:
Mono and dihydroxypyrrolidinones are readily available by direct oxygenation of a pyroglutamate-derived bicyclic lactam with high diastereoselectivity, and these may be manipulated further in protected or unprotected form by Grignard addition to a pendant Weinreb amide to give acylhydroxypyrrolidinones, which are analogues of the natural product, pramanicin. Preliminary bioassay against S. aureus and E. coli indicated that some compounds exhibit selective Gram-negative antibacterial activity, and may offer promise for the development of novel systems suitable for antibacterial drug development.
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