(Q24618792)

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Genome mining in streptomyces. Discovery of an unprecedented P450-catalyzed oxidative rearrangement that is the final step in the biosynthesis of pentalenolactone

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scholarly article

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Genome mining in streptomyces. Discovery of an unprecedented P450-catalyzed oxidative rearrangement that is the final step in the biosynthesis of pentalenolactone (English)

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pentalenolactone F(1-)

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ChEBI release 2020-05-28

pentalenolactone F

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ChEBI release 2020-05-28

pentalenolactone

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ChEBI release 2020-05-28

pentalenolactone(1-)

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ChEBI release 2020-05-28

Streptomyces arenae

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Streptomyces exfoliatus

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Streptomyces avermitilis

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methyl (1R,4aR,6aS,9aR)-8,8-dimethyl-2-oxospiro[4a,6a,7,9-tetrahydro-4H-pentaleno[1,6a-c]pyran-1,2'-oxirane]-5-carboxylate

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object named as

Myung-Ji Seo

2

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author name string

Dongqing Zhu

1

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Haruo Ikeda

3

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David E Cane

4

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language of work or name

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publication date

1 February 2011

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16 September 2022

full work available at URL

https://europepmc.org/articles/pmc3041837?pdf=render

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19 March 2024

https://api.unpaywall.org/v2/10.1021/ja111279h?email=unpaywall_01@example.com

Journal of the American Chemical Society

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133

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7

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2128-31

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online access status

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19 March 2024

https://api.unpaywall.org/v2/10.1021/ja111279h?email=unpaywall_01@example.com

access restriction status

1 reference

based on heuristic

inferred from online access status

Genome mining in Streptomyces. Elucidation of the role of Baeyer-Villiger monooxygenases and non-heme iron-dependent dehydrogenase/oxygenases in the final steps of the biosynthesis of pentalenolactone and neopentalenolactone

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3041837

7 April 2017

Pentalenic acid is a shunt metabolite in the biosynthesis of the pentalenolactone family of metabolites: hydroxylation of 1-deoxypentalenic acid mediated by CYP105D7 (SAV_7469) of Streptomyces avermitilis

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3041837

7 April 2017

Hydrocarbon hydroxylation by cytochrome P450 enzymes

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3041837

7 April 2017

Crystal structure of the non-heme iron dioxygenase PtlH in pentalenolactone biosynthesis

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3041837

7 April 2017

Pentalenolactone biosynthesis: Molecular cloning and assignment of biochemical function to PtlF, a short-chain dehydrogenase from Streptomyces avermitilis, and identification of a new biosynthetic intermediate

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3041837

7 April 2017

Pentalenolactone biosynthesis. Molecular cloning and assignment of biochemical function to PtlI, a cytochrome P450 of Streptomyces avermitilis

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3041837

7 April 2017

Pentalenolactone biosynthesis. Molecular cloning and assignment of biochemical function to PtlH, a non-heme iron dioxygenase of Streptomyces avermitilis

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3041837

7 April 2017

Radical intermediates in the catalytic oxidation of hydrocarbons by bacterial and human cytochrome P450 enzymes

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3041837

7 April 2017

The catalytic pathway of cytochrome p450cam at atomic resolution

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3041837

7 April 2017

Crystal structure of pentalenene synthase: mechanistic insights on terpenoid cyclization reactions in biology

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3041837

7 April 2017

Pentalenene synthase. Purification, molecular cloning, sequencing, and high-level expression in Escherichia coli of a terpenoid cyclase from Streptomyces UC5319

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3041837

7 April 2017

Cytochrome P450 compound I: capture, characterization, and C-H bond activation kinetics

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3041837

27 September 2017

Genome sequence of the milbemycin-producing bacterium Streptomyces bingchenggensis

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3041837

27 September 2017

Genome mining in Streptomyces avermitilis: A biochemical Baeyer-Villiger reaction and discovery of a new branch of the pentalenolactone family tree

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3041837

27 September 2017

A gene cluster for biosynthesis of the sesquiterpenoid antibiotic pentalenolactone in Streptomyces avermitilis

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3041837

27 September 2017

Structure and chemistry of cytochrome P450.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3041837

27 September 2017

Complete genome sequence and comparative analysis of the industrial microorganism Streptomyces avermitilis

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3041837

27 September 2017

PCR-targeted Streptomyces gene replacement identifies a protein domain needed for biosynthesis of the sesquiterpene soil odor geosmin

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3041837

27 September 2017

A complex multienzyme system encoded by five polyketide synthase genes is involved in the biosynthesis of the 26-membered polyene macrolide pimaricin in Streptomyces natalensis

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3041837

27 September 2017

Radical mechanisms in adenosylmethionine- and adenosylcobalamin-dependent enzymatic reactions

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3041837

27 September 2017

Arenaemycin (pentalenolactone): a specific inhibitor of glycolysis

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3041837

27 September 2017

Characterization of a silent sesquiterpenoid biosynthetic pathway in Streptomyces avermitilis controlling epi-isozizaene albaflavenone biosynthesis and isolation of a new oxidized epi-isozizaene metabolite.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3041837

30 May 2018

Studies on biosynthesis of pentalenolactone. V isolation of deoxypentalenylglucuron.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3041837

30 May 2018

Inhibition of glyceraldehyde-3-phosphate dehydrogenase by pentalenolactone: kinetic and mechanistic studies

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3041837

30 May 2018

Inhibition of glyceraldehyde-3-phosphate dehydrogenase by pentalenolactone. 2. Identification of the site of alkylation by tetrahydropentalenolactone.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3041837

28 November 2018

The structure of pentalenolactone (PA-132)Setsuo Takeuchi

1 reference

https://pubmed.ncbi.nlm.nih.gov/21284395

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

The structure and absolute configuration of pentalenolactone (PA 132)

1 reference

https://pubmed.ncbi.nlm.nih.gov/21284395

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

[Metabolic products of microorganisms. 105. Arenacemycin E, D and C]

1 reference

https://pubmed.ncbi.nlm.nih.gov/21284395

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Studies on the biosynthesis of pentalenolactone. VII. Isolation of pentalenolactones P and O

1 reference

https://pubmed.ncbi.nlm.nih.gov/21284395

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

PA 132, a new antibiotic. I. Isolation and chemical properties

1 reference

https://pubmed.ncbi.nlm.nih.gov/21284395

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

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10.1021/JA111279H

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