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Biosynthesis of the sesquiterpene antibiotic albaflavenone in Streptomyces coelicolor A3(2)

B Zhao, X Lin, L Lei, L Lei, DC Lamb, Steven Kelly Orcid Logo, MR Waterman, DE Cane

Journal of Biological Chemistry, Volume: 203, Issue: 12, Pages: 8183 - 9

Swansea University Author: Steven Kelly Orcid Logo

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DOI (Published version): 10.1074/jbc.M710421200

Abstract

Cytochrome P450 170A1 (CYP170A1) is encoded by the sco5223 gene of the Gram-positive, soil-dwelling bacterium Streptomyces coelicolor A3(2) as part of a two-gene cluster with the sco5222 gene. The SCO5222 protein is a sesquiterpene synthase that catalyzes the cyclization of farnesyl diphosphate to t...

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Published in: Journal of Biological Chemistry
Published: 9650 ROCKVILLE PIKE, BETHESDA, MD 20814-3996 USA AMER SOC BIOCHEMISTRY MOLECULAR BIOLOGY INC 2008
URI: https://cronfa.swan.ac.uk/Record/cronfa10337
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spelling 2021-10-26T17:05:53.7026401 v2 10337 2012-03-21 Biosynthesis of the sesquiterpene antibiotic albaflavenone in Streptomyces coelicolor A3(2) b17cebaf09b4d737b9378a3581e3de93 0000-0001-7991-5040 Steven Kelly Steven Kelly true false 2012-03-21 BMS Cytochrome P450 170A1 (CYP170A1) is encoded by the sco5223 gene of the Gram-positive, soil-dwelling bacterium Streptomyces coelicolor A3(2) as part of a two-gene cluster with the sco5222 gene. The SCO5222 protein is a sesquiterpene synthase that catalyzes the cyclization of farnesyl diphosphate to the novel tricyclic hydrocarbon, epi-isozizaene (Lin, X., Hopson, R., and Cane, D. E. (2006) J. Am. Chem. Soc. 128, 6022 - 6023). The presence of CYP170A1 (sco5223) suggested that epiisozizaene might be further oxidized by the transcriptionally coupled P450. We have now established that purified CYP170A1 carries out two sequential allylic oxidations to convert epi-isozizaene to an epimeric mixture of albaflavenols and thence to the sesquiterpene antibiotic albaflavenone. Gas chromatography/ mass spectrometry analysis of S. coelicolor culture extracts established the presence of albaflavenone in the wildtype strain, along with its precursors epi-isozizaene and the albaflavenols. Disruption of the CYP170A1 gene abolished biosynthesis of both albaflavenone and the albaflavenols, but not epi-isozizaene. The combined results establish for the first time the presence of albaflavenone in S. coelicolor and clearly demonstrate that the biosynthesis of this antibiotic involves the coupled action of epi-isozizaene synthase and CYP170A1. Journal Article Journal of Biological Chemistry 203 12 8183 9 AMER SOC BIOCHEMISTRY MOLECULAR BIOLOGY INC 9650 ROCKVILLE PIKE, BETHESDA, MD 20814-3996 USA CYTOCHROME-P450 COMPLEMENT CYPOME; COMPLETE GENOME SEQUENCE; MOLECULAR-CLONING; AVERMITILIS; ACID; HYDROXYLATIONS; METABOLITES; MECHANISM; PATHWAY; BINDING 31 3 2008 2008-03-31 10.1074/jbc.M710421200 COLLEGE NANME Biomedical Sciences COLLEGE CODE BMS Swansea University 2021-10-26T17:05:53.7026401 2012-03-21T16:17:29.0000000 Faculty of Medicine, Health and Life Sciences Swansea University Medical School - Medicine B Zhao 1 X Lin 2 L Lei 3 L Lei 4 DC Lamb 5 Steven Kelly 0000-0001-7991-5040 6 MR Waterman 7 DE Cane 8
title Biosynthesis of the sesquiterpene antibiotic albaflavenone in Streptomyces coelicolor A3(2)
spellingShingle Biosynthesis of the sesquiterpene antibiotic albaflavenone in Streptomyces coelicolor A3(2)
Steven Kelly
title_short Biosynthesis of the sesquiterpene antibiotic albaflavenone in Streptomyces coelicolor A3(2)
title_full Biosynthesis of the sesquiterpene antibiotic albaflavenone in Streptomyces coelicolor A3(2)
title_fullStr Biosynthesis of the sesquiterpene antibiotic albaflavenone in Streptomyces coelicolor A3(2)
title_full_unstemmed Biosynthesis of the sesquiterpene antibiotic albaflavenone in Streptomyces coelicolor A3(2)
title_sort Biosynthesis of the sesquiterpene antibiotic albaflavenone in Streptomyces coelicolor A3(2)
author_id_str_mv b17cebaf09b4d737b9378a3581e3de93
author_id_fullname_str_mv b17cebaf09b4d737b9378a3581e3de93_***_Steven Kelly
author Steven Kelly
author2 B Zhao
X Lin
L Lei
L Lei
DC Lamb
Steven Kelly
MR Waterman
DE Cane
format Journal article
container_title Journal of Biological Chemistry
container_volume 203
container_issue 12
container_start_page 8183
publishDate 2008
institution Swansea University
doi_str_mv 10.1074/jbc.M710421200
publisher AMER SOC BIOCHEMISTRY MOLECULAR BIOLOGY INC
college_str Faculty of Medicine, Health and Life Sciences
hierarchytype
hierarchy_top_id facultyofmedicinehealthandlifesciences
hierarchy_top_title Faculty of Medicine, Health and Life Sciences
hierarchy_parent_id facultyofmedicinehealthandlifesciences
hierarchy_parent_title Faculty of Medicine, Health and Life Sciences
department_str Swansea University Medical School - Medicine{{{_:::_}}}Faculty of Medicine, Health and Life Sciences{{{_:::_}}}Swansea University Medical School - Medicine
document_store_str 0
active_str 0
description Cytochrome P450 170A1 (CYP170A1) is encoded by the sco5223 gene of the Gram-positive, soil-dwelling bacterium Streptomyces coelicolor A3(2) as part of a two-gene cluster with the sco5222 gene. The SCO5222 protein is a sesquiterpene synthase that catalyzes the cyclization of farnesyl diphosphate to the novel tricyclic hydrocarbon, epi-isozizaene (Lin, X., Hopson, R., and Cane, D. E. (2006) J. Am. Chem. Soc. 128, 6022 - 6023). The presence of CYP170A1 (sco5223) suggested that epiisozizaene might be further oxidized by the transcriptionally coupled P450. We have now established that purified CYP170A1 carries out two sequential allylic oxidations to convert epi-isozizaene to an epimeric mixture of albaflavenols and thence to the sesquiterpene antibiotic albaflavenone. Gas chromatography/ mass spectrometry analysis of S. coelicolor culture extracts established the presence of albaflavenone in the wildtype strain, along with its precursors epi-isozizaene and the albaflavenols. Disruption of the CYP170A1 gene abolished biosynthesis of both albaflavenone and the albaflavenols, but not epi-isozizaene. The combined results establish for the first time the presence of albaflavenone in S. coelicolor and clearly demonstrate that the biosynthesis of this antibiotic involves the coupled action of epi-isozizaene synthase and CYP170A1.
published_date 2008-03-31T03:11:41Z
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score 11.013731

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