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Biosynthetic studies of the notoamides: isotopic synthesis of stephacidin A and incorporation into notoamide B and sclerotiamide.

ABSTRACT: The advanced natural product stephacidin A is proposed as a biosynthetic precursor to notoamide B in various Aspergillus species. Doubly (13)C-labeled racemic stephacidin A was synthesized and fed to cultures of the terrestrial-derived fungus, Aspergillus versicolor NRRL 35600, and the marine-derived fungus, Aspergillus sp. MF297-2. Analysis of the metabolites revealed enantiospecific incorporation of intact (-)-stephacidin A into (+)-notoamide B in Aspergillus versicolor and (+)-stephacidin A into (-)-notoamide B in Aspergillus sp. MF297-2. (13)C-Labeled sclerotiamide was also isolated from both fungal cultures.

SUBMITTER: Finefield JM

PROVIDER: S-EPMC3146567 | biostudies-literature | 2011 Aug

REPOSITORIES: biostudies-literature

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Biosynthetic studies of the notoamides: isotopic synthesis of stephacidin A and incorporation into notoamide B and sclerotiamide.

Finefield Jennifer M JM Kato Hikaru H Greshock Thomas J TJ Sherman David H DH Tsukamoto Sachiko S Williams Robert M RM

Organic letters 20110630 15

The advanced natural product stephacidin A is proposed as a biosynthetic precursor to notoamide B in various Aspergillus species. Doubly (13)C-labeled racemic stephacidin A was synthesized and fed to cultures of the terrestrial-derived fungus, Aspergillus versicolor NRRL 35600, and the marine-derived fungus, Aspergillus sp. MF297-2. Analysis of the metabolites revealed enantiospecific incorporation of intact (-)-stephacidin A into (+)-notoamide B in Aspergillus versicolor and (+)-stephacidin A i ...[more]

PMID: 21714564

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