Synthesis of Norfijimycin A with Activity against Mycobacterium tuberculosis

Alexander Stoye; Gayathri Nagalingam; Warwick J. Britton; Richard J. Payne

doi:10.1071/CH16559

RESEARCH ARTICLE

Previous Contents Vol 70(2)

Synthesis of Norfijimycin A with Activity against Mycobacterium tuberculosis

Alexander Stoye ^A , Gayathri Nagalingam ^B , Warwick J. Britton ^B and Richard J. Payne ^A ^C

+ Author Affiliations

- Author Affiliations

^A School of Chemistry, The University of Sydney, Sydney, NSW 2006, Australia.

^B Tuberculosis Research Program, Centenary Institute, and Sydney Medical School, The University of Sydney, Sydney, NSW 2006, Australia.

^C Corresponding author. Email: richard.payne@sydney.edu.au

Australian Journal of Chemistry 70(2) 229-232 https://doi.org/10.1071/CH16559
Submitted: 2 October 2016 Accepted: 15 November 2016 Published: 9 December 2016

Abstract

The total synthesis of norfijimycin A, a simplified analogue of the marine natural product fijimycin A, is described. Fijimycin A is a cyclic depsipeptide that has been shown to possess activity against methicillin-resistant Staphylococcus aureus. The natural product contains a rare N,β-dimethyl leucine unit with unknown stereochemistry at the β-carbon. To evaluate the importance of the β-methyl group for antimicrobial activity, we introduced N-methyl leucine into the natural product scaffold. The resulting norfijimycin A was shown to possess significant activity against Mycobacterium tuberculosis, the etiological agent of tuberculosis.

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Synthesis of Norfijimycin A with Activity against Mycobacterium tuberculosis

Abstract

References

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