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Biosynthesis of the Antibiotic Echinosporin by a Novel Branch of the Shikimate Pathway
Author(s) -
Dübeler Anke,
Krastel Philipp,
Floss Heinz G.,
Zeeck Axel
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200203)2002:6<983::aid-ejoc983>3.0.co;2-m
Subject(s) - shikimate pathway , chemistry , shikimic acid , biosynthesis , stereochemistry , aromatic amino acids , metabolite , streptomyces , amino acid , biochemistry , bacteria , enzyme , biology , genetics
Echinosporin ( 1 ), a known antibiotic with a unique tricyclic acetal‐lactone structure, is produced by Streptomyces erythraeus (strain Tü 4015), together with the novel 7‐deoxyechinosporin ( 2 ) as minor compound, which was fully characterized. The biosynthesis of 1 was established by feeding experiments with 13 C‐labelled precursors. The results revealed that 1 was formed by the shikimate pathway, with chorismate as a biosynthetic intermediate. The proposed mechanism for the conversion of chorismate into 1 represents a new branch of the shikimate pathway, producing a nonaromatic metabolite. In addition, the influence of aromatic amino acids and of glyphosate, an inhibitor in the shikimate pathway of plants, was investigated. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)