title: Structural Reassignment and Absolute Stereochemistry of Madurastatin C1 (MBJ-0034) and the Related Aziridine Siderophores: Madurastatins A1, B1, and MBJ-0035.
abstract: The 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.
authors.forename: Andrew R
authors.initials: AR
authors.lastname: Tyler
authors.forename: Hamed
authors.initials: H
authors.lastname: Mosaei
authors.forename: Stephanie
authors.initials: S
authors.lastname: Morton
authors.forename: Paul G
authors.initials: PG
authors.lastname: Waddell
authors.forename: Corinne
authors.initials: C
authors.lastname: Wills
authors.forename: William
authors.initials: W
authors.lastname: McFarlane
authors.forename: Joe
authors.initials: J
authors.lastname: Gray
authors.forename: Michael
authors.initials: M
authors.lastname: Goodfellow
authors.affiliation: Demuris Limited, Newcastle Biomedicine Bio-Incubators , Framlington Place, Newcastle upon Tyne, NE2 4HH, U.K.
authors.forename: Jeff
authors.identifier: 0000-0002-6977-9388
authors.initials: J
authors.lastname: Errington
authors.affiliation: Demuris Limited, Newcastle Biomedicine Bio-Incubators , Framlington Place, Newcastle upon Tyne, NE2 4HH, U.K.
authors.forename: Nick
authors.initials: N
authors.lastname: Allenby
authors.forename: Nikolay
authors.initials: N
authors.lastname: Zenkin
authors.forename: Michael J
authors.identifier: 0000-0001-6475-9161
authors.initials: MJ
authors.lastname: Hall
mesh_terms: D001388:Aziridines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009842:Oligopeptides / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry*; D010881:Piperidones / Q000737:chemistry*; D017262:Siderophores / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001388:Aziridines; C000594031:MBJ-0034; C000594032:MBJ-0035; D009842:Oligopeptides; D010455:Peptides; D010881:Piperidones; D017262:Siderophores; C000622199:madurastatin A1; C000622200:madurastatin B1; C573847:madurastatin C1