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JM47, a cyclic tetrapeptide HC-toxin analogue from a marine Fusarium species

Lookup NU author(s): Professor Grant Burgess

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Abstract

The known metabolite, enniatin B, and a cyclic tetrapeptide, JM47, which is a new natural product, were extracted from brown rice cultures of a marine fungus, identified as a Fusarium species, isolated from the marine alga Codium fragile. NMR studies, including 15N HMQC and 15N HMBC, established the structure of JM47 as cyclo(Ala-Ala-Aoh-Pro), where Aoh is the amino acid, (2S,9S)-2-amino-8-oxo-9-hydroxydecanoic acid. The absolute stereochemistry of the Aoh side chain carbinol centre was determined using Mosher ester methodology. Analysis of NOESY data assisted by molecular modelling revealed an alternating L-, D-, L-, D-configuration for the tetrapeptide core. The absolute stereochemistry of the core was determined by acidic hydrolysis and chiral TLC analysis of the proline residue. JM47 belongs to the HC-toxin family of cyclic tetrapeptides which possess a 2-amino-8-oxo-9,10-epoxydecanoic acid residue in place of the Aoh unit. This is the first report of an analogue of HC-toxin from a marine Fusarium species.


Publication metadata

Author(s): Burgess JG; Jiang Z; Barret MO; Boyd KG; Adams DR; Boyd ASF

Publication type: Article

Publication status: Published

Journal: Phytochemistry

Year: 2002

Volume: 60

Issue: 1

Pages: 33-38

ISSN (print): 0031-9422

ISSN (electronic): 1873-3700

Publisher: Pergamon

URL: http://dx.doi.org/10.1016/S0031-9422(02)00061-4

DOI: 10.1016/S0031-9422(02)00061-4

PubMed id: 11985849


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