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Structural Reassignment and Absolute Stereochemistry of Madurastatin C1 (MBJ-0034) and the Related Aziridine Siderophores: Madurastatins A1, B1, and MBJ-0035

Tyler, Andrew R., Mosaei, Hamed, Morton, Stephanie, Waddell, Paul G., Wills, Corinne, McFarlane, William, Gray, Joe, Goodfellow, Michael, Errington, Jeff, Allenby, Nick, Zenkin, Nikolay and Hall, Michael J. (2017) Structural Reassignment and Absolute Stereochemistry of Madurastatin C1 (MBJ-0034) and the Related Aziridine Siderophores: Madurastatins A1, B1, and MBJ-0035. Journal of Natural Products, 80 (5). pp. 1558-1562. ISSN 0163-3864

Item Type: Article

Abstract

he madurastatins are pentapeptide siderophores originally described as containing an unusual salicylate-capped N-terminal aziridine ring. Isolation of madurastatin C1 (1) (also designated MBJ-0034), from Actinomadura sp. DEM31376 (itself isolated from a deep sea sediment), prompted structural reevaluation of the madurastatin siderophores, in line with the recent work of Thorson and Shaaban. NMR spectroscopy in combination with partial synthesis allowed confirmation of the structure of madurastatin C1 (1) as containing an N-terminal 2-(2-hydroxyphenyl)oxazoline in place of the originally postulated aziridine, while absolute stereochemistry was determined via Harada’s advanced Marfey’s method. Therefore, this work further supports Thorson and Shaaban’s proposed structural revision of the madurastatin class of siderophores (madurastatins A1 (2), B1 (3), C1 (1), and MBJ-0036 (4)) as N-terminal 2-(2-hydroxyphenyl)oxazolines.

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Additional Information: ““This document is the Accepted Manuscript version of a Published Work that appeared in final form in the Journal of Natural Products, copyright © 2017 The American Chemical Society and American Society of Pharmacognosy after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.jnatprod.7b00082.”
Depositing User: Nick Allenby

Identifiers

Item ID: 17404
Identification Number: https://doi.org/10.1021/acs.jnatprod.7b00082
ISSN: 0163-3864
URI: http://sure.sunderland.ac.uk/id/eprint/17404
Official URL: http://dx.doi.org/10.1021/acs.jnatprod.7b00082

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Catalogue record

Date Deposited: 29 Feb 2024 10:31
Last Modified: 29 Feb 2024 10:31

Contributors

Author: Andrew R. Tyler
Author: Hamed Mosaei
Author: Stephanie Morton
Author: Paul G. Waddell
Author: Corinne Wills
Author: William McFarlane
Author: Joe Gray
Author: Michael Goodfellow
Author: Jeff Errington
Author: Nick Allenby
Author: Nikolay Zenkin
Author: Michael J. Hall

University Divisions

Faculty of Health Sciences and Wellbeing

Subjects

Sciences > Biomedical Sciences

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