Coupled biosynthesis of volatiles and salinosporamideA in Salinispora tropica

TitleCoupled biosynthesis of volatiles and salinosporamideA in Salinispora tropica
Publication TypeJournal Article
Year of Publication2016
AuthorsGroenhagen U., De Oliveira A.LL, Fielding E., Moore BS, Schulz S.
JournalChembiochem
Volume17
Pagination1978-1985
Date Published2016/10
Type of ArticleArticle
ISBN Number1439-4227
Accession NumberWOS:000386772300014
Keywordsactinomycetes; amino acids; bacteria; esters; genome data; geosmin; identification; marine; Marine bacteria; metabolites; natural products; natural-products; prephenate; proteasome inhibitors; spiroacetals
Abstract

Terrestrial bacteria, especially actinomycetes, are known to be prolific producers of volatile compounds. We show here that bacteria from ocean sediments can also release complex bouquets of volatiles. The actinomycete Salinispora tropica produces cyclohexenyl compounds not previously known in nature, such as methyl cyclohex-2-ene-1-carboxylate (9), methyl 2-(cyclohex-2-en-1-yl)acetate (10), methyl (E/Z)-2-(cyclohex-2-en-1-ylidene)acetate (11/12), and related alcohols 8 and 13. These compounds were identified by GC/MS and confirmed by synthesis. In addition, rare spiroacetals, aromatic compounds, short-chain acids and esters, alcohols, and various cyclic compounds were produced by the bacteria. The biosynthesis of the cyclohexenyl compounds is closely coupled to that of cyclohexenylalanine (4), a building block of salinosporamideA, a proteasome inhibitor produced by S.tropica. Analysis of S.tropica strains that harbor knockouts of the salinosporamide biosynthetic genes salX and salD, coupled with feeding experiments, revealed that 3-(cyclohex-2-en-1-yl)-2-oxopropanoic acid (60) and 3-(cyclohex-2-en-1-ylidene)-2-oxopropanoic acid (isomers 61 and 62) are important intermediates in the biosynthesis of salinosporamideA, 4, and 8-13.

DOI10.1002/cbic.201600388
Short TitleChemBioChem
Student Publication: 
No
Research Topics: 
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