« Previous AbstractEngineering resistance to virus transmission    Next AbstractIsolation of a functional vesicular intermediate that mediates ER to Golgi transport in yeast »

Chembiochem

Title:		Coupled Biosynthesis of Volatiles and Salinosporamide A in Salinispora tropica
Author(s):		Groenhagen U; Leandrini De Oliveira AL; Fielding E; Moore BS; Schulz S;
Address:		"Institute of Organic Chemistry, Technische Universitat Braunschweig, Hagenring 30, 38106, Braunschweig, Germany. Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California San Diego, 9500 Gilman Drive, La Jolla, CA, 92093, USA. Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego, 9500 Gilman Drive, La Jolla, CA, 92093, USA. Institute of Organic Chemistry, Technische Universitat Braunschweig, Hagenring 30, 38106, Braunschweig, Germany. stefan.schulz@tu-bs.de"
Journal Title:		Chembiochem
Year:		2016
Volume:		20160906
Issue:		20
Page Number:		1978 - 1985
DOI:		10.1002/cbic.201600388
ISSN/ISBN:		1439-7633 (Electronic) 1439-4227 (Print) 1439-4227 (Linking)
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 salinosporamide A, 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 salinosporamide A, 4, and 8-13"
Keywords:		Actinobacteria/*metabolism Lactones/chemistry/*metabolism Molecular Structure Pyrroles/chemistry/*metabolism Volatile Organic Compounds/chemistry/*metabolism actinomycetes amino acids marine bacteria natural products spiroacetals;
Notes:		"MedlineGroenhagen, Ulrike Leandrini De Oliveira, Ana Ligia Fielding, Elisha Moore, Bradley S Schulz, Stefan eng R01 CA127622/CA/NCI NIH HHS/ Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't Germany 2016/10/21 Chembiochem. 2016 Oct 17; 17(20):1978-1985. doi: 10.1002/cbic.201600388. Epub 2016 Sep 6"