Unknown

Dataset Information

0

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.

SUBMITTER: Tyler AR 

PROVIDER: S-EPMC6544507 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature

altmetric image

Publications

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

Tyler Andrew R AR   Mosaei Hamed H   Morton Stephanie S   Waddell Paul G PG   Wills Corinne C   McFarlane William W   Gray Joe J   Goodfellow Michael M   Errington Jeff J   Allenby Nick N   Zenkin Nikolay N   Hall Michael J MJ  

Journal of natural products 20170411 5


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 madurasta  ...[more]

Similar Datasets

| S-EPMC2824046 | biostudies-literature
| S-EPMC2504520 | biostudies-literature
| S-EPMC2496922 | biostudies-other
| S-EPMC6491662 | biostudies-literature
| S-EPMC4571416 | biostudies-literature
| S-EPMC5628338 | biostudies-literature
| S-EPMC3165044 | biostudies-literature
| S-EPMC3850515 | biostudies-literature
| S-EPMC8145716 | biostudies-literature
| S-EPMC3352666 | biostudies-literature