Structure of epi-isozizaene synthase from Streptomyces coelicolor A3(2), a platform for new terpenoid cyclization templates.

PubWeight™: 1.27‹?› | Rank: Top 10%

🔗 View Article (PMC 2840623)

Published in Biochemistry on March 02, 2010

Authors

Julie A Aaron1, Xin Lin, David E Cane, David W Christianson

Author Affiliations

1: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.

Articles citing this

Terpenoid synthase structures: a so far incomplete view of complex catalysis. Nat Prod Rep (2012) 1.39

Exploration and mining of the bacterial terpenome. Acc Chem Res (2011) 1.21

Bacterial diterpene synthases: new opportunities for mechanistic enzymology and engineered biosynthesis. Curr Opin Chem Biol (2012) 1.15

Dedicated ent-kaurene and ent-atiserene synthases for platensimycin and platencin biosynthesis. Proc Natl Acad Sci U S A (2011) 1.15

Insights into diterpene cyclization from structure of bifunctional abietadiene synthase from Abies grandis. J Biol Chem (2012) 1.09

Characterization of a silent sesquiterpenoid biosynthetic pathway in Streptomyces avermitilis controlling epi-isozizaene albaflavenone biosynthesis and isolation of a new oxidized epi-isozizaene metabolite. Microb Biotechnol (2010) 1.07

Structure of isoprene synthase illuminates the chemical mechanism of teragram atmospheric carbon emission. J Mol Biol (2010) 1.05

Traversing the fungal terpenome. Nat Prod Rep (2014) 1.04

Two distinct mechanisms for TIM barrel prenyltransferases in bacteria. J Am Chem Soc (2011) 0.96

Selectivity of fungal sesquiterpene synthases: role of the active site's H-1 alpha loop in catalysis. Appl Environ Microbiol (2010) 0.90

Reprogramming the chemodiversity of terpenoid cyclization by remolding the active site contour of epi-isozizaene synthase. Biochemistry (2014) 0.88

Mechanistic insights from the binding of substrate and carbocation intermediate analogues to aristolochene synthase. Biochemistry (2013) 0.88

Head-to-head prenyl tranferases: anti-infective drug targets. J Med Chem (2012) 0.86

Emergence of terpene cyclization in Artemisia annua. Nat Commun (2015) 0.83

Protein engineering towards natural product synthesis and diversification. J Ind Microbiol Biotechnol (2011) 0.83

Unexpected reactivity of 2-fluorolinalyl diphosphate in the active site of crystalline 2-methylisoborneol synthase. Biochemistry (2013) 0.81

Predicting the functions and specificity of triterpenoid synthases: a mechanism-based multi-intermediate docking approach. PLoS Comput Biol (2014) 0.81

Probing the mechanism of 1,4-conjugate elimination reactions catalyzed by terpene synthases. J Am Chem Soc (2012) 0.80

Purification, crystallization and preliminary X-ray diffraction analysis of Omp6, a protoilludene synthase from Omphalotus olearius. Acta Crystallogr Sect F Struct Biol Cryst Commun (2013) 0.77

A Terpene Synthase Is Involved in the Synthesis of the Volatile Organic Compound Sodorifen of Serratia plymuthica 4Rx13. Front Microbiol (2016) 0.76

Structural Studies of Geosmin Synthase, a Bifunctional Sesquiterpene Synthase with αα Domain Architecture That Catalyzes a Unique Cyclization-Fragmentation Reaction Sequence. Biochemistry (2015) 0.76

Dynamic behavior of rearranging carbocations - implications for terpene biosynthesis. Beilstein J Org Chem (2016) 0.76

Identification and activation of novel biosynthetic gene clusters by genome mining in the kirromycin producer Streptomyces collinus Tü 365. J Ind Microbiol Biotechnol (2015) 0.75

Nature as organic chemist. J Antibiot (Tokyo) (2016) 0.75

Crystallization and preliminary X-ray diffraction analysis of the diterpene cyclooctatin synthase (CYC) from Streptomyces sp. LZ35. Acta Crystallogr F Struct Biol Commun (2014) 0.75

Identification of amino acid networks governing catalysis in the closed complex of class I terpene synthases. Proc Natl Acad Sci U S A (2016) 0.75

Structural Basis of Catalysis in the Bacterial Monoterpene Synthases Linalool Synthase and 1,8-Cineole Synthase. ACS Catal (2017) 0.75

Structural and Chemical Biology of Terpenoid Cyclases. Chem Rev (2017) 0.75

Articles cited by this

Coot: model-building tools for molecular graphics. Acta Crystallogr D Biol Crystallogr (2004) 227.01

Improved methods for building protein models in electron density maps and the location of errors in these models. Acta Crystallogr A (1991) 119.63

PHENIX: building new software for automated crystallographic structure determination. Acta Crystallogr D Biol Crystallogr (2002) 53.61

Likelihood-enhanced fast rotation functions. Acta Crystallogr D Biol Crystallogr (2004) 23.86

Automated structure solution with autoSHARP. Methods Mol Biol (2007) 14.67

Version 1.2 of the Crystallography and NMR system. Nat Protoc (2007) 13.01

The Cationminus signpi Interaction. Chem Rev (1997) 7.56

Structural basis for cyclic terpene biosynthesis by tobacco 5-epi-aristolochene synthase. Science (1997) 5.56

Structural biology and chemistry of the terpenoid cyclases. Chem Rev (2006) 4.90

Crystal structure of pentalenene synthase: mechanistic insights on terpenoid cyclization reactions in biology. Science (1997) 4.63

Crystal structure of recombinant farnesyl diphosphate synthase at 2.6-A resolution. Biochemistry (1994) 3.10

Designed divergent evolution of enzyme function. Nature (2006) 3.09

Bornyl diphosphate synthase: structure and strategy for carbocation manipulation by a terpenoid cyclase. Proc Natl Acad Sci U S A (2002) 2.44

Terpene synthases and the regulation, diversity and biological roles of terpene metabolism. Curr Opin Plant Biol (2006) 2.34

Structure of trichodiene synthase from Fusarium sporotrichioides provides mechanistic inferences on the terpene cyclization cascade. Proc Natl Acad Sci U S A (2001) 2.22

Unearthing the roots of the terpenome. Curr Opin Chem Biol (2008) 2.00

Quantitative exploration of the catalytic landscape separating divergent plant sesquiterpene synthases. Nat Chem Biol (2008) 1.77

Crystal structure determination of aristolochene synthase from the blue cheese mold, Penicillium roqueforti. J Biol Chem (2000) 1.66

Structure of limonene synthase, a simple model for terpenoid cyclase catalysis. Proc Natl Acad Sci U S A (2007) 1.64

Aristolochene synthase: mechanistic analysis of active site residues by site-directed mutagenesis. J Am Chem Soc (2004) 1.55

Managing and manipulating carbocations in biology: terpenoid cyclase structure and mechanism. Curr Opin Struct Biol (1998) 1.52

Pentalenene synthase. Analysis of active site residues by site-directed mutagenesis. J Am Chem Soc (2002) 1.50

X-ray crystal structure of aristolochene synthase from Aspergillus terreus and evolution of templates for the cyclization of farnesyl diphosphate. Biochemistry (2007) 1.49

Biosynthesis of the sesquiterpene antibiotic albaflavenone in Streptomyces coelicolor A3(2). J Biol Chem (2008) 1.48

Genome mining in Streptomyces coelicolor: molecular cloning and characterization of a new sesquiterpene synthase. J Am Chem Soc (2006) 1.44

Albaflavenone, a sesquiterpene ketone with a zizaene skeleton produced by a streptomycete with a new rope morphology. J Antibiot (Tokyo) (1994) 1.32

On the origin of enzymatic species. Trends Biochem Sci (1993) 1.31

Evolving biosynthetic tangos negotiate mechanistic landscapes. Nat Chem Biol (2008) 1.24

Crystal structure of (+)-delta-cadinene synthase from Gossypium arboreum and evolutionary divergence of metal binding motifs for catalysis. Biochemistry (2009) 1.19

Exploring biosynthetic diversity with trichodiene synthase. Arch Biochem Biophys (2007) 1.18

Biosynthesis of the sesquiterpene antibiotic albaflavenone in Streptomyces coelicolor. Mechanism and stereochemistry of the enzymatic formation of epi-isozizaene. J Am Chem Soc (2009) 1.11

X-ray crystallographic studies of substrate binding to aristolochene synthase suggest a metal ion binding sequence for catalysis. J Biol Chem (2008) 1.07

Consequences of conformational preorganization in sesquiterpene biosynthesis: theoretical studies on the formation of the bisabolene, curcumene, acoradiene, zizaene, cedrene, duprezianene, and sesquithuriferol sesquiterpenes. J Am Chem Soc (2009) 1.01

Retention index calculation without n-alkanes--the virtual carbon number. J Chromatogr A (2003) 0.87

Articles by these authors

The E3 ligase TRAF6 regulates Akt ubiquitination and activation. Science (2009) 4.63

The adaptor protein CARD9 is required for innate immune responses to intracellular pathogens. Nat Immunol (2006) 3.76

A requirement for CARMA1 in TCR-induced NF-kappa B activation. Nat Immunol (2002) 3.38

Phosphorylation of CARMA1 plays a critical role in T Cell receptor-mediated NF-kappaB activation. Immunity (2005) 3.14

HDAC8 mutations in Cornelia de Lange syndrome affect the cohesin acetylation cycle. Nature (2012) 3.08

Endothelial arginase II: a novel target for the treatment of atherosclerosis. Circ Res (2008) 2.70

Structure and mechanism of the 6-deoxyerythronolide B synthase. Annu Rev Biochem (2007) 2.65

The 2.7-Angstrom crystal structure of a 194-kDa homodimeric fragment of the 6-deoxyerythronolide B synthase. Proc Natl Acad Sci U S A (2006) 2.63

Inducible NO synthase dependent S-nitrosylation and activation of arginase1 contribute to age-related endothelial dysfunction. Circ Res (2007) 2.62

Bornyl diphosphate synthase: structure and strategy for carbocation manipulation by a terpenoid cyclase. Proc Natl Acad Sci U S A (2002) 2.44

Ubiquitination of RIP is required for tumor necrosis factor alpha-induced NF-kappaB activation. J Biol Chem (2006) 2.32

Genome-minimized Streptomyces host for the heterologous expression of secondary metabolism. Proc Natl Acad Sci U S A (2010) 2.29

Differential use of CARD9 by dectin-1 in macrophages and dendritic cells. J Immunol (2009) 2.23

Evaluation of terrestrial carbon cycle models for their response to climate variability and to CO2 trends. Glob Chang Biol (2013) 2.13

Structural and mechanistic analysis of protein interactions in module 3 of the 6-deoxyerythronolide B synthase. Chem Biol (2007) 2.02

The effect of combined antihypertensive treatment (felodipine with either irbesartan or metoprolol) on erectile function: a randomized controlled trial. Cardiology (2013) 2.02

CD3/CD28 costimulation-induced NF-kappaB activation is mediated by recruitment of protein kinase C-theta, Bcl10, and IkappaB kinase beta to the immunological synapse through CARMA1. Mol Cell Biol (2004) 1.96

Constitutively active type I insulin-like growth factor receptor causes transformation and xenograft growth of immortalized mammary epithelial cells and is accompanied by an epithelial-to-mesenchymal transition mediated by NF-kappaB and snail. Mol Cell Biol (2007) 1.89

Crucial role for nuclear factor of activated T cells in T cell receptor-mediated regulation of human interleukin-17. J Biol Chem (2004) 1.77

Arginase inhibition restores NOS coupling and reverses endothelial dysfunction and vascular stiffness in old rats. J Appl Physiol (1985) (2009) 1.76

Solution structure and proposed domain domain recognition interface of an acyl carrier protein domain from a modular polyketide synthase. Protein Sci (2007) 1.68

Interaction between P-TEFb and the C-terminal domain of RNA polymerase II activates transcriptional elongation from sites upstream or downstream of target genes. Mol Cell Biol (2002) 1.68

Structural studies of human histone deacetylase 8 and its site-specific variants complexed with substrate and inhibitors. Biochemistry (2008) 1.68

A gene cluster for biosynthesis of the sesquiterpenoid antibiotic pentalenolactone in Streptomyces avermitilis. Biochemistry (2006) 1.67

Proinflammatory protein CARD9 is essential for infiltration of monocytic fibroblast precursors and cardiac fibrosis caused by Angiotensin II infusion. Am J Hypertens (2011) 1.67

Arginase I suppresses IL-12/IL-23p40-driven intestinal inflammation during acute schistosomiasis. J Immunol (2010) 1.67

Quantitative analysis of the relative contributions of donor acyl carrier proteins, acceptor ketosynthases, and linker regions to intermodular transfer of intermediates in hybrid polyketide synthases. Biochemistry (2002) 1.66

Extender unit and acyl carrier protein specificity of ketosynthase domains of the 6-deoxyerythronolide B synthase. J Am Chem Soc (2006) 1.63

Structure of human epoxide hydrolase reveals mechanistic inferences on bifunctional catalysis in epoxide and phosphate ester hydrolysis. Biochemistry (2004) 1.59

Evidence of recombination and genetic diversity in human rhinoviruses in children with acute respiratory infection. PLoS One (2009) 1.58

NF-κB signaling pathways regulated by CARMA family of scaffold proteins. Cell Res (2010) 1.58

Stereospecificity of ketoreductase domains of the 6-deoxyerythronolide B synthase. J Am Chem Soc (2007) 1.56

Aristolochene synthase: mechanistic analysis of active site residues by site-directed mutagenesis. J Am Chem Soc (2004) 1.55

Genome-wide search for type 2 diabetes/impaired glucose homeostasis susceptibility genes in the Chinese: significant linkage to chromosome 6q21-q23 and chromosome 1q21-q24. Diabetes (2004) 1.54

Phosphorylation and ubiquitination of the IkappaB kinase complex by two distinct signaling pathways. EMBO J (2007) 1.54

Biosynthesis of the earthy odorant geosmin by a bifunctional Streptomyces coelicolor enzyme. Nat Chem Biol (2007) 1.53

Crystal structure of LpxC, a zinc-dependent deacetylase essential for endotoxin biosynthesis. Proc Natl Acad Sci U S A (2003) 1.52

Positive and negative signaling components involved in TNFalpha-induced NF-kappaB activation. Cytokine (2008) 1.50

Pentalenene synthase. Analysis of active site residues by site-directed mutagenesis. J Am Chem Soc (2002) 1.50

Geosmin biosynthesis. Streptomyces coelicolor germacradienol/germacrene D synthase converts farnesyl diphosphate to geosmin. J Am Chem Soc (2006) 1.49

X-ray crystal structure of aristolochene synthase from Aspergillus terreus and evolution of templates for the cyclization of farnesyl diphosphate. Biochemistry (2007) 1.49

Taxadiene synthase structure and evolution of modular architecture in terpene biosynthesis. Nature (2010) 1.49

Biosynthesis of the sesquiterpene antibiotic albaflavenone in Streptomyces coelicolor A3(2). J Biol Chem (2008) 1.48

Effect of felodipine with irbesartan or metoprolol on sexual function and oxidative stress in women with essential hypertension. J Hypertens (2012) 1.47

Reconstituting modular activity from separated domains of 6-deoxyerythronolide B synthase. Biochemistry (2004) 1.47

C-type lectin receptors Dectin-3 and Dectin-2 form a heterodimeric pattern-recognition receptor for host defense against fungal infection. Immunity (2013) 1.46

Crystal structure of human arginase I at 1.29-A resolution and exploration of inhibition in the immune response. Proc Natl Acad Sci U S A (2005) 1.46

Stat3 activation of NF-{kappa}B p100 processing involves CBP/p300-mediated acetylation. Proc Natl Acad Sci U S A (2006) 1.46

Structure-based dissociation of a type I polyketide synthase module. Chem Biol (2007) 1.46

Insights into channel architecture and substrate specificity from crystal structures of two macrocycle-forming thioesterases of modular polyketide synthases. Biochemistry (2002) 1.45

Tracing conidial fate and measuring host cell antifungal activity using a reporter of microbial viability in the lung. Cell Rep (2012) 1.45

CARMA3 deficiency abrogates G protein-coupled receptor-induced NF-{kappa}B activation. Genes Dev (2007) 1.45

CARMA1-mediated NF-kappaB and JNK activation in lymphocytes. Immunol Rev (2009) 1.44

Bcl10 plays a critical role in NF-kappaB activation induced by G protein-coupled receptors. Proc Natl Acad Sci U S A (2006) 1.44

Genome mining in Streptomyces coelicolor: molecular cloning and characterization of a new sesquiterpene synthase. J Am Chem Soc (2006) 1.44

The CARMA1-Bcl10 signaling complex selectively regulates JNK2 kinase in the T cell receptor-signaling pathway. Immunity (2006) 1.40

Engineered Streptomyces avermitilis host for heterologous expression of biosynthetic gene cluster for secondary metabolites. ACS Synth Biol (2013) 1.40

The biochemical basis for stereochemical control in polyketide biosynthesis. J Am Chem Soc (2009) 1.39

Declining snow cover may affect spring phenological trend on the Tibetan Plateau. Proc Natl Acad Sci U S A (2013) 1.38

MALT1/paracaspase is a signaling component downstream of CARMA1 and mediates T cell receptor-induced NF-kappaB activation. J Biol Chem (2004) 1.38

Design of amino acid sulfonamides as transition-state analogue inhibitors of arginase. J Am Chem Soc (2003) 1.37

Trinuclear Metal Clusters in Catalysis by Terpenoid Synthases. Pure Appl Chem (2010) 1.35

Structure, mechanism, and inhibition of histone deacetylases and related metalloenzymes. Curr Opin Struct Biol (2011) 1.35

Early airway pressure release ventilation prevents ARDS-a novel preventive approach to lung injury. Shock (2013) 1.35

Crystal structure of human liver Delta4-3-ketosteroid 5beta-reductase (AKR1D1) and implications for substrate binding and catalysis. J Biol Chem (2008) 1.34

Polyketide double bond biosynthesis. Mechanistic analysis of the dehydratase-containing module 2 of the picromycin/methymycin polyketide synthase. J Am Chem Soc (2005) 1.33

Structure and mechanism of the diterpene cyclase ent-copalyl diphosphate synthase. Nat Chem Biol (2011) 1.33

Arginase and vascular aging. J Appl Physiol (1985) (2008) 1.33

UDP-3-O-((R)-3-hydroxymyristoyl)-N-acetylglucosamine deacetylase functions through a general acid-base catalyst pair mechanism. J Biol Chem (2005) 1.32

Human soluble epoxide hydrolase: structural basis of inhibition by 4-(3-cyclohexylureido)-carboxylic acids. Protein Sci (2005) 1.32

X-ray crystal structures of D100E trichodiene synthase and its pyrophosphate complex reveal the basis for terpene product diversity. Biochemistry (2002) 1.31

The E3 ubiquitin ligase GRAIL regulates T cell tolerance and regulatory T cell function by mediating T cell receptor-CD3 degradation. Immunity (2010) 1.31

Human arginase II: crystal structure and physiological role in male and female sexual arousal. Biochemistry (2003) 1.30

Revisiting the modularity of modular polyketide synthases. Curr Opin Chem Biol (2009) 1.30

TAK1 is recruited to the tumor necrosis factor-alpha (TNF-alpha) receptor 1 complex in a receptor-interacting protein (RIP)-dependent manner and cooperates with MEKK3 leading to NF-kappaB activation. J Biol Chem (2005) 1.28

High-order interactions among genetic variants in DNA base excision repair pathway genes and smoking in bladder cancer susceptibility. Cancer Epidemiol Biomarkers Prev (2007) 1.27

Molecular recognition between ketosynthase and acyl carrier protein domains of the 6-deoxyerythronolide B synthase. Proc Natl Acad Sci U S A (2010) 1.27

Structural basis of the antiproliferative activity of largazole, a depsipeptide inhibitor of the histone deacetylases. J Am Chem Soc (2011) 1.26

CARD9 facilitates microbe-elicited production of reactive oxygen species by regulating the LyGDI-Rac1 complex. Nat Immunol (2009) 1.26

Mechanistic inferences from the binding of ligands to LpxC, a metal-dependent deacetylase. Biochemistry (2006) 1.25

Loss-of-function HDAC8 mutations cause a phenotypic spectrum of Cornelia de Lange syndrome-like features, ocular hypertelorism, large fontanelle and X-linked inheritance. Hum Mol Genet (2014) 1.25

Mechanistic analysis of acyl transferase domain exchange in polyketide synthase modules. J Am Chem Soc (2003) 1.24

RGD-modified apoferritin nanoparticles for efficient drug delivery to tumors. ACS Nano (2013) 1.23

Thioredoxin-like 2 regulates human cancer cell growth and metastasis via redox homeostasis and NF-κB signaling. J Clin Invest (2010) 1.22

Stereospecificity of ketoreductase domains 1 and 2 of the tylactone modular polyketide synthase. J Am Chem Soc (2008) 1.22

Mechanism and stereochemistry of the germacradienol/germacrene D synthase of Streptomyces coelicolor A3(2). J Am Chem Soc (2004) 1.21

NF-kappaB2/p52 enhances androgen-independent growth of human LNCaP cells via protection from apoptotic cell death and cell cycle arrest induced by androgen-deprivation. Prostate (2008) 1.21

Molecular recognition of the substrate diphosphate group governs product diversity in trichodiene synthase mutants. Biochemistry (2005) 1.20

Cell signalling through thromboxane A2 receptors. Cell Signal (2004) 1.20

Beta-arrestin 2 is required for lysophosphatidic acid-induced NF-kappaB activation. Proc Natl Acad Sci U S A (2008) 1.20

Sesquiterpene synthase from the botrydial biosynthetic gene cluster of the phytopathogen Botrytis cinerea. ACS Chem Biol (2008) 1.19

Crystal structure of (+)-delta-cadinene synthase from Gossypium arboreum and evolutionary divergence of metal binding motifs for catalysis. Biochemistry (2009) 1.19

Reprogramming a module of the 6-deoxyerythronolide B synthase for iterative chain elongation. Proc Natl Acad Sci U S A (2012) 1.19

Structure and mechanism of the trans-acting acyltransferase from the disorazole synthase. Biochemistry (2011) 1.18

Exploring biosynthetic diversity with trichodiene synthase. Arch Biochem Biophys (2007) 1.18