Biosynthesis of the sesquiterpene antibiotic albaflavenone in Streptomyces coelicolor. Mechanism and stereochemistry of the enzymatic formation of epi-isozizaene

scientific article published in May 2009

Biosynthesis of the sesquiterpene antibiotic albaflavenone in Streptomyces coelicolor. Mechanism and stereochemistry of the enzymatic formation of epi-isozizaene is …
instance of (P31):
scholarly articleQ13442814

External links are
P356DOI10.1021/JA901313V
P953full work available at URLhttps://europepmc.org/articles/pmc2690639?pdf=render
P932PMC publication ID2690639
P698PubMed publication ID19385616
P5875ResearchGate publication ID24348945

P7228access restriction statusopen accessQ232932
P2093author name stringXin Lin
David E Cane
P2860cites workRetention index calculation without n-alkanes—the virtual carbon numberQ73364927
Biosynthesis of the sesquiterpene antibiotic albaflavenone in Streptomyces coelicolor A3(2)Q24648509
X-ray crystal structures of D100E trichodiene synthase and its pyrophosphate complex reveal the basis for terpene product diversityQ27637618
Pentalenene synthase. Analysis of active site residues by site-directed mutagenesisQ27639254
Exploring biosynthetic diversity with trichodiene synthaseQ27646952
Stereochemistry and deuterium isotope effects associated with the cyclization-rearrangements catalyzed by tobacco epiaristolochene and hyoscyamus premnaspirodiene synthases, and the chimeric CH4 hybrid cyclaseQ33904011
Genome mining in Streptomyces coelicolor: molecular cloning and characterization of a new sesquiterpene synthaseQ34521000
Structural biology and chemistry of the terpenoid cyclasesQ34555232
Volatile metabolites from actinomycetesQ43962448
Aristolochene synthase: mechanistic analysis of active site residues by site-directed mutagenesisQ44928346
Molecular recognition of the substrate diphosphate group governs product diversity in trichodiene synthase mutants.Q46441880
Albaflavenone, a sesquiterpene ketone with a zizaene skeleton produced by a streptomycete with a new rope morphologyQ72465130
P433issue18
P407language of work or nameEnglishQ1860
P921main subjectantibioticQ12187
farnesyl pyrophosphateQ2699676
Streptomyces coelicolorQ2355919
beta-SesquiphellandreneQ104253613
KhuseneQ104386375
(1R,2S)-2,6,7,7-tetramethyltricyclo[6.2.1.01,5]undec-5-eneQ104972396
(5R)-1alpha-Isopropenyl-4alpha,8-dimethylspiro[4.5]deca-7-eneQ104989811
SesquisabineneQ104991594
(1R,2S)-2,6,7,7-tetramethyltricyclo[6.2.1.01,5]undec-5-en-4-oneQ105253220
(1S,5R)-1,8-dimethyl-4-propan-2-ylspiro[4.5]dec-8-eneQ115949455
phosphono [(4R,7E)-2,4,12-trimethyltrideca-2,7,11-trien-4-yl] hydrogen phosphateQ115949500
(1S,2R)-2,6,6,8-tetramethyltricyclo[5.3.1.01,5]undec-8-eneQ115949537
Streptomyces albidoflavusQ22286833
(6E)-β-farneseneQ27108631
albaflavenoneQ27122616
P6954online access statusopen accessQ232932
P304page(s)6332-6333
P577publication date2009-04-22
P1433published inJournal of the American Chemical SocietyQ898902
P1476titleBiosynthesis of the sesquiterpene antibiotic albaflavenone in Streptomyces coelicolor. Mechanism and stereochemistry of the enzymatic formation of epi-isozizaene
P478volume131

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cites work (P2860)
Q57865551Albaflavenoid, a new tricyclic sesquiterpenoid from Streptomyces violascens
Q52586153Antartin, a Cytotoxic Zizaane-Type Sesquiterpenoid from a Streptomyces sp. Isolated from an Antarctic Marine Sediment.
Q91993694Bacterial terpene biosynthesis: challenges and opportunities for pathway engineering
Q38632052Bacterial terpene cyclases
Q42198206Characterization of a silent sesquiterpenoid biosynthetic pathway in Streptomyces avermitilis controlling epi-isozizaene albaflavenone biosynthesis and isolation of a new oxidized epi-isozizaene metabolite.
Q39189530Cold-water marine natural products, 2006 to 2016.
Q92906413Comparative Genomic Insights into Secondary Metabolism Biosynthetic Gene Cluster Distributions of Marine Streptomyces
Q93167652Complete genome sequence of high-yield strain S. lincolnensis B48 and identification of crucial mutations contributing to lincomycin overproduction
Q26747304Dynamic behavior of rearranging carbocations - implications for terpene biosynthesis
Q37951089Exploration and mining of the bacterial terpenome
Q38132682Genome mining of the Streptomyces avermitilis genome and development of genome-minimized hosts for heterologous expression of biosynthetic gene clusters
Q34711979Genomic basis for natural product biosynthetic diversity in the actinomycetes
Q42322628Identification by Genome Mining of a Type I Polyketide Gene Cluster from Streptomyces argillaceus Involved in the Biosynthesis of Pyridine and Piperidine Alkaloids Argimycins P.
Q34239126Investigating conservation of the albaflavenone biosynthetic pathway and CYP170 bifunctionality in streptomycetes
Q37943241Isoprenoids in three-dimensional space: the stereochemistry of terpene biosynthesis
Q36792146Mechanism of Germacradien-4-ol Synthase-Controlled Water Capture.
Q48187055Mechanistic Characterization of Two Chimeric Sesterterpene Synthases from Penicillium
Q47103620Modulation of inherent dynamical tendencies of the bisabolyl cation via preorganization in epi-isozizaene synthase
Q34096062Natural products version 2.0: connecting genes to molecules.
Q88006908Nature as organic chemist
Q47806618Nucleophilic Water Capture or Proton Loss: Single Amino Acid Switch Converts δ-Cadinene Synthase into Germacradien-4-ol Synthase.
Q27681677Reprogramming the Chemodiversity of Terpenoid Cyclization by Remolding the Active Site Contour of epi -Isozizaene Synthase
Q33862680Sesquiterpene synthases Cop4 and Cop6 from Coprinus cinereus: catalytic promiscuity and cyclization of farnesyl pyrophosphate geometric isomers.
Q34231014Sesquiterpene synthases: passive catalysts or active players?
Q27659994Structural Elucidation of Cisoid and Transoid Cyclization Pathways of a Sesquiterpene Synthase Using 2-Fluorofarnesyl Diphosphates
Q41069472Structural Revision and Elucidation of the Biosynthesis of Hypodoratoxide by (13) C,(13) C COSY NMR Spectroscopy
Q41036841Structural and Chemical Biology of Terpenoid Cyclases.
Q27659507Structure of Epi-Isozizaene Synthase from Streptomyces coelicolor A3(2), a Platform for New Terpenoid Cyclization Templates ,
Q47716925Substitution of Aromatic Residues with Polar Residues in the Active Site Pocket of epi-Isozizaene Synthase Leads to the Generation of New Cyclic Sesquiterpenes.
Q92013312The Chemistry, Pharmacology and Therapeutic Potential of the Edible Mushroom Dictyophora indusiata (Vent ex. Pers.) Fischer (Synn. Phallus indusiatus)
Q51277521The T296V Mutant of Amorpha-4,11-diene Synthase Is Defective in Allylic Diphosphate Isomerization but Retains the Ability To Cyclize the Intermediate (3R)-Nerolidyl Diphosphate to Amorpha-4,11-diene.
Q27690683The first structure of a bacterial diterpene cyclase: CotB2
Q42729229Trinuclear Metal Clusters in Catalysis by Terpenoid Synthases
Q35045304Volatile terpenes from actinomycetes: a biosynthetic study correlating chemical analyses to genome data

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