Thiazole and oxazole peptides: biosynthesis and molecular machinery.

PubWeight™: 1.63‹?› | Rank: Top 4%

🔗 View Article (PMID 10331285)

Published in Nat Prod Rep on April 01, 1999

Authors

R S Roy1, A M Gehring, J C Milne, P J Belshaw, C T Walsh

Author Affiliations

1: Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, Boston, MA 02115, USA.

Articles citing this

Plasmid-mediated quinolone resistance: a multifaceted threat. Clin Microbiol Rev (2009) 4.43

Discovery of a widely distributed toxin biosynthetic gene cluster. Proc Natl Acad Sci U S A (2008) 3.20

Ribosomal peptide natural products: bridging the ribosomal and nonribosomal worlds. Nat Prod Rep (2009) 2.32

Manipulation of thiocillin variants by prepeptide gene replacement: structure, conformation, and activity of heterocycle substitution mutants. J Am Chem Soc (2010) 1.51

Structural and functional dissection of the heterocyclic peptide cytotoxin streptolysin S. J Biol Chem (2009) 1.50

Marine molecular machines: heterocyclization in cyanobactin biosynthesis. Chembiochem (2010) 1.50

Expansion of ribosomally produced natural products: a nitrile hydratase- and Nif11-related precursor family. BMC Biol (2010) 1.49

Plantazolicin, a novel microcin B17/streptolysin S-like natural product from Bacillus amyloliquefaciens FZB42. J Bacteriol (2010) 1.47

Thiazolyl peptide antibiotic biosynthesis: a cascade of post-translational modifications on ribosomal nascent proteins. J Biol Chem (2010) 1.41

Identification and localization of the gene cluster encoding biosynthesis of the antitumor macrolactam leinamycin in Streptomyces atroolivaceus S-140. J Bacteriol (2002) 1.38

Flavoenzymes: versatile catalysts in biosynthetic pathways. Nat Prod Rep (2013) 1.23

In vitro characterization of DNA gyrase inhibition by microcin B17 analogs with altered bisheterocyclic sites. Proc Natl Acad Sci U S A (2001) 1.23

NMR, mass spectrometry and chemical evidence reveal a different chemical structure for methanobactin that contains oxazolone rings. J Am Chem Soc (2008) 1.19

How nature morphs peptide scaffolds into antibiotics. Chembiochem (2009) 1.14

Chemistry and biology of the copper chelator methanobactin. ACS Chem Biol (2011) 1.13

Three ring posttranslational circuses: insertion of oxazoles, thiazoles, and pyridines into protein-derived frameworks. ACS Chem Biol (2012) 1.11

Identification and analysis of the biosynthetic gene cluster encoding the thiopeptide antibiotic cyclothiazomycin in Streptomyces hygroscopicus 10-22. Appl Environ Microbiol (2010) 1.08

Isolation and characterization of the gene cluster for biosynthesis of the thiopeptide antibiotic TP-1161. Appl Environ Microbiol (2010) 1.03

Mollamides B and C, Cyclic hexapeptides from the indonesian tunicate Didemnum molle. J Nat Prod (2008) 0.95

Total synthesis of the marine cyanobacterial cyclodepsipeptide apratoxin A. Proc Natl Acad Sci U S A (2004) 0.84

Genetic analysis of polyketide synthase and peptide synthetase genes in cyanobacteria as a mining tool for secondary metabolites. J Ind Microbiol Biotechnol (2007) 0.84

Marine natural products with P-glycoprotein inhibitor properties. Mar Drugs (2014) 0.82

Iterative Mechanism of Macrodiolide Formation in the Anticancer Compound Conglobatin. Chem Biol (2015) 0.80

YcaO-Dependent Posttranslational Amide Activation: Biosynthesis, Structure, and Function. Chem Rev (2017) 0.79

Polyketide-nonribosomal peptide epothilone antitumor agents: the EpoA, B, C subunits. J Ind Microbiol Biotechnol (2003) 0.79

Biomimetic Synthesis of Cbz-(S)-Dolaphenine. Tetrahedron Lett (2012) 0.79

Mechanisms of cyanobactin biosynthesis. Curr Opin Chem Biol (2016) 0.76

3-bromohomofascaplysin A, a fascaplysin analogue from a Fijian Didemnum sp. ascidian. Bioorg Med Chem (2011) 0.75

Intracellular Targeting Mechanisms by Antimicrobial Peptides. Antimicrob Agents Chemother (2017) 0.75

Didemnaketals f and g, new bioactive spiroketals from a red sea ascidian didemnum species. Mar Drugs (2014) 0.75

Structural and mutational analysis of the nonribosomal peptide synthetase heterocyclization domain provides insight into catalysis. Proc Natl Acad Sci U S A (2016) 0.75

Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides. Beilstein J Org Chem (2016) 0.75

Cysteine isocyanide in multicomponent reaction: Synthesis of peptido-mimetic 1,3-azoles. J Org Chem (2017) 0.75

Synthesis of the heterocyclic core of the D-series GE2270. Beilstein J Org Chem (2017) 0.75

Inter- versus intra-molecular cyclization of tripeptides containing tetrahydrofuran amino acids: a density functional theory study on kinetic control. J Mol Model (2012) 0.75

Articles by these authors

Functional association of cyclophilin A with HIV-1 virions. Nature (1994) 6.82

Molecular basis for vancomycin resistance in Enterococcus faecium BM4147: biosynthesis of a depsipeptide peptidoglycan precursor by vancomycin resistance proteins VanH and VanA. Biochemistry (1991) 5.90

The behavior and significance of slow-binding enzyme inhibitors. Adv Enzymol Relat Areas Mol Biol (1988) 5.84

A new enzyme superfamily - the phosphopantetheinyl transferases. Chem Biol (1996) 4.71

Characterization of Sfp, a Bacillus subtilis phosphopantetheinyl transferase for peptidyl carrier protein domains in peptide synthetases. Biochemistry (1998) 3.96

Identification of a Mycobacterium tuberculosis gene cluster encoding the biosynthetic enzymes for assembly of the virulence-conferring siderophore mycobactin. Chem Biol (1998) 3.89

Harnessing the biosynthetic code: combinations, permutations, and mutations. Science (1998) 3.87

Transcriptional regulation of the Enterococcus faecium BM4147 vancomycin resistance gene cluster by the VanS-VanR two-component regulatory system in Escherichia coli K-12. J Bacteriol (1997) 3.80

Identification of vancomycin resistance protein VanA as a D-alanine:D-alanine ligase of altered substrate specificity. Biochemistry (1991) 3.76

From peptide precursors to oxazole and thiazole-containing peptide antibiotics: microcin B17 synthase. Science (1996) 3.74

Inhibition of T cell signaling by immunophilin-ligand complexes correlates with loss of calcineurin phosphatase activity. Biochemistry (1992) 3.05

Human cyclophilin B: a second cyclophilin gene encodes a peptidyl-prolyl isomerase with a signal sequence. Proc Natl Acad Sci U S A (1991) 2.70

Molecular biology of carbon-phosphorus bond cleavage. Cloning and sequencing of the phn (psiD) genes involved in alkylphosphonate uptake and C-P lyase activity in Escherichia coli B. J Biol Chem (1990) 2.59

Intracellular steps of bacterial cell wall peptidoglycan biosynthesis: enzymology, antibiotics, and antibiotic resistance. Nat Prod Rep (1992) 2.46

Localization of labile posttranslational modifications by electron capture dissociation: the case of gamma-carboxyglutamic acid. Anal Chem (1999) 2.43

Active site mutants of human cyclophilin A separate peptidyl-prolyl isomerase activity from cyclosporin A binding and calcineurin inhibition. Protein Sci (1992) 2.40

Vancomycin resistance: structure of D-alanine:D-alanine ligase at 2.3 A resolution. Science (1994) 2.38

Iron acquisition in plague: modular logic in enzymatic biogenesis of yersiniabactin by Yersinia pestis. Chem Biol (1998) 2.35

Oligomerization activates c-Raf-1 through a Ras-dependent mechanism. Nature (1996) 2.29

Peptidyl-prolyl cis-trans-isomerase from Escherichia coli: a periplasmic homolog of cyclophilin that is not inhibited by cyclosporin A. Proc Natl Acad Sci U S A (1990) 2.29

Bacterial carbon-phosphorus lyase: products, rates, and regulation of phosphonic and phosphinic acid metabolism. J Bacteriol (1987) 2.26

The parallel and convergent universes of polyketide synthases and nonribosomal peptide synthetases. Chem Biol (1999) 2.25

Enterobactin biosynthesis in Escherichia coli: isochorismate lyase (EntB) is a bifunctional enzyme that is phosphopantetheinylated by EntD and then acylated by EntE using ATP and 2,3-dihydroxybenzoate. Biochemistry (1997) 2.19

Cloning, expression, and purification of human cyclophilin in Escherichia coli and assessment of the catalytic role of cysteines by site-directed mutagenesis. Proc Natl Acad Sci U S A (1990) 2.14

Reconstitution and characterization of the Escherichia coli enterobactin synthetase from EntB, EntE, and EntF. Biochemistry (1998) 2.13

Activation of the SH2-containing phosphotyrosine phosphatase SH-PTP2 by its binding site, phosphotyrosine 1009, on the human platelet-derived growth factor receptor. J Biol Chem (1993) 2.13

Formation of cyanide from carbon 1 of 1-aminocyclopropane-1-carboxylic acid during its conversion to ethylene. Proc Natl Acad Sci U S A (1984) 2.12

Purification and properties of an 8-hydroxy-5-deazaflavin-reducing hydrogenase from Methanobacterium thermoautotrophicum. J Biol Chem (1982) 2.08

Post-translational modification of polyketide and nonribosomal peptide synthases. Curr Opin Chem Biol (1997) 2.05

MurA (MurZ), the enzyme that catalyzes the first committed step in peptidoglycan biosynthesis, is essential in Escherichia coli. J Bacteriol (1995) 2.01

Structure of the detoxification catalyst mercuric ion reductase from Bacillus sp. strain RC607. Nature (1991) 2.01

Evidence for in vivo incorporation of D-lactate into peptidoglycan precursors of vancomycin-resistant enterococci. Antimicrob Agents Chemother (1992) 1.99

Purification and characterization of VanR and the cytosolic domain of VanS: a two-component regulatory system required for vancomycin resistance in Enterococcus faecium BM4147. Biochemistry (1993) 1.99

Mercuric reductase. Purification and characterization of a transposon-encoded flavoprotein containing an oxidation-reduction-active disulfide. J Biol Chem (1982) 1.95

Biosynthetic thiolase from Zoogloea ramigera. III. Isolation and characterization of the structural gene. J Biol Chem (1987) 1.94

Suicide substrates, mechanism-based enzyme inactivators: recent developments. Annu Rev Biochem (1984) 1.94

Cross-talk between the histidine protein kinase VanS and the response regulator PhoB. Characterization and identification of a VanS domain that inhibits activation of PhoB. J Biol Chem (1995) 1.93

Protein-tyrosine-phosphatase SHPTP2 couples platelet-derived growth factor receptor beta to Ras. Proc Natl Acad Sci U S A (1994) 1.92

Cofactor requirements and reconstitution of microcin B17 synthetase: a multienzyme complex that catalyzes the formation of oxazoles and thiazoles in the antibiotic microcin B17. Biochemistry (1999) 1.91

Mutational analysis of potential zinc-binding residues in the active site of the enterococcal D-Ala-D-Ala dipeptidase VanX. Biochemistry (1997) 1.86

Cyclosporin-mediated inhibition of bovine calcineurin by cyclophilins A and B. Proc Natl Acad Sci U S A (1992) 1.85

Cloning, overproduction, and characterization of the Escherichia coli holo-acyl carrier protein synthase. J Biol Chem (1995) 1.81

Identification of the DNA-binding site for the phosphorylated VanR protein required for vancomycin resistance in Enterococcus faecium. Biochemistry (1994) 1.79

Biosynthesis of the Escherichia coli siderophore enterobactin: sequence of the entF gene, expression and purification of EntF, and analysis of covalent phosphopantetheine. Biochemistry (1991) 1.79

Peptide cyclization catalysed by the thioesterase domain of tyrocidine synthetase. Nature (2000) 1.79

The MerR metalloregulatory protein binds mercuric ion as a tricoordinate, metal-bridged dimer. Science (1990) 1.76

Kinetic comparison of the specificity of the vancomycin resistance VanSfor two response regulators, VanR and PhoB. Biochemistry (1996) 1.74

The antibiotic microcin B17 is a DNA gyrase poison: characterisation of the mode of inhibition. J Mol Biol (2001) 1.74

Characterization of vanY, a DD-carboxypeptidase from vancomycin-resistant Enterococcus faecium BM4147. Antimicrob Agents Chemother (1992) 1.73

Aminoacyl-CoAs as probes of condensation domain selectivity in nonribosomal peptide synthesis. Science (1999) 1.70

Structure of the UDP-glucosyltransferase GtfB that modifies the heptapeptide aglycone in the biosynthesis of vancomycin group antibiotics. Structure (2001) 1.69

Hsp90 chaperonins possess ATPase activity and bind heat shock transcription factors and peptidyl prolyl isomerases. J Biol Chem (1993) 1.67

Potent stimulation of SH-PTP2 phosphatase activity by simultaneous occupancy of both SH2 domains. J Biol Chem (1995) 1.66

The residual enzymatic phosphorylation activity of hexokinase II mutants is correlated with glucose repression in Saccharomyces cerevisiae. Mol Cell Biol (1989) 1.66

Two alanine racemase genes in Salmonella typhimurium that differ in structure and function. J Bacteriol (1983) 1.65

Use of a site-directed triple mutant to trap intermediates: demonstration that the flavin C(4a)-thiol adduct and reduced flavin are kinetically competent intermediates in mercuric ion reductase. Biochemistry (1990) 1.63

Acinetobacter cyclohexanone monooxygenase: gene cloning and sequence determination. J Bacteriol (1988) 1.63

Characterization of a Cys115 to Asp substitution in the Escherichia coli cell wall biosynthetic enzyme UDP-GlcNAc enolpyruvyl transferase (MurA) that confers resistance to inactivation by the antibiotic fosfomycin. Biochemistry (1996) 1.63

Purification and characterization of trypanothione reductase from Crithidia fasciculata, a newly discovered member of the family of disulfide-containing flavoprotein reductases. Biochemistry (1986) 1.62

Existence of two D-alanine:D-alanine ligases in Escherichia coli: cloning and sequencing of the ddlA gene and purification and characterization of the DdlA and DdlB enzymes. Biochemistry (1991) 1.62

Kinetics, stoichiometry, and identification of the reactive thiolate in the inactivation of UDP-GlcNAc enolpyruvoyl transferase by the antibiotic fosfomycin. Biochemistry (1994) 1.62

A hydrogenase-linked gene in Methanobacterium thermoautotrophicum strain delta H encodes a polyferredoxin. Proc Natl Acad Sci U S A (1989) 1.61

Functional analysis of Fas signaling in vivo using synthetic inducers of dimerization. Curr Biol (1996) 1.60

Crystal structure of recombinant human T-cell cyclophilin A at 2.5 A resolution. Proc Natl Acad Sci U S A (1991) 1.60

Cloning and sequencing of Escherichia coli murZ and purification of its product, a UDP-N-acetylglucosamine enolpyruvyl transferase. J Bacteriol (1992) 1.59

Subcloning, expression, and purification of the enterobactin biosynthetic enzyme 2,3-dihydroxybenzoate-AMP ligase: demonstration of enzyme-bound (2,3-dihydroxybenzoyl)adenylate product. Biochemistry (1989) 1.59

The nonribosomal peptide synthetase HMWP2 forms a thiazoline ring during biogenesis of yersiniabactin, an iron-chelating virulence factor of Yersinia pestis. Biochemistry (1998) 1.58

Overexpression, purification, and characterization of VanX, a D-, D-dipeptidase which is essential for vancomycin resistance in Enterococcus faecium BM4147. Biochemistry (1995) 1.56

Nucleotide sequence of a cluster of Escherichia coli enterobactin biosynthesis genes: identification of entA and purification of its product 2,3-dihydro-2,3-dihydroxybenzoate dehydrogenase. J Bacteriol (1989) 1.54

Binuclear [2Fe-2S] clusters in the Escherichia coli SoxR protein and role of the metal centers in transcription. J Biol Chem (1995) 1.53

Initiation, elongation, and termination strategies in polyketide and polypeptide antibiotic biosynthesis. Curr Opin Chem Biol (1999) 1.52

Homologs of the vancomycin resistance D-Ala-D-Ala dipeptidase VanX in Streptomyces toyocaensis, Escherichia coli and Synechocystis: attributes of catalytic efficiency, stereoselectivity and regulation with implications for function. Chem Biol (1998) 1.51

The EntF and EntE adenylation domains of Escherichia coli enterobactin synthetase: sequestration and selectivity in acyl-AMP transfers to thiolation domain cosubstrates. Proc Natl Acad Sci U S A (2000) 1.50

Overexpression, purification, and characterization of isochorismate synthase (EntC), the first enzyme involved in the biosynthesis of enterobactin from chorismate. Biochemistry (1990) 1.49

Posttranslational heterocyclization of cysteine and serine residues in the antibiotic microcin B17: distributivity and directionality. Biochemistry (1999) 1.49

Altered recognition mutants of the response regulator PhoB: a new genetic strategy for studying protein-protein interactions. Proc Natl Acad Sci U S A (1996) 1.48

ATP/GTP hydrolysis is required for oxazole and thiazole biosynthesis in the peptide antibiotic microcin B17. Biochemistry (1998) 1.47

Acetylenic enzyme inactivators. Inactivation of gamma-cystathionase, in vitro and in vivo, by propargylglycine. J Am Chem Soc (1973) 1.47

Activation of the SH2-containing protein tyrosine phosphatase, SH-PTP2, by phosphotyrosine-containing peptides derived from insulin receptor substrate-1. J Biol Chem (1994) 1.46

Homologous metalloregulatory proteins from both gram-positive and gram-negative bacteria control transcription of mercury resistance operons. J Bacteriol (1989) 1.46

A common fold for peptide synthetases cleaving ATP to ADP: glutathione synthetase and D-alanine:d-alanine ligase of Escherichia coli. Proc Natl Acad Sci U S A (1995) 1.46

Bacterial organomercurial lyase: overproduction, isolation, and characterization. Biochemistry (1986) 1.46

Biosynthetic thiolase from zoogloea ramigera. I. Preliminary characterization and analysis of proton transfer reaction. J Biol Chem (1987) 1.44

The LIM region of a presumptive Caenorhabditis elegans transcription factor is an iron-sulfur- and zinc-containing metallodomain. Proc Natl Acad Sci U S A (1991) 1.44

Human and Escherichia coli cyclophilins: sensitivity to inhibition by the immunosuppressant cyclosporin A correlates with a specific tryptophan residue. Biochemistry (1991) 1.44

Studies on the mechanism of action of D-amino acid oxidase. Evidence for removal of substrate -hydrogen as a proton. J Biol Chem (1971) 1.44

Reconstitution and characterization of the Vibrio cholerae vibriobactin synthetase from VibB, VibE, VibF, and VibH. Biochemistry (2000) 1.43

Cyclophilin B trafficking through the secretory pathway is altered by binding of cyclosporin A. Proc Natl Acad Sci U S A (1994) 1.43

Assembly line enzymology by multimodular nonribosomal peptide synthetases: the thioesterase domain of E. coli EntF catalyzes both elongation and cyclolactonization. Chem Biol (1999) 1.43

Involvement of the phosphate regulon and the psiD locus in carbon-phosphorus lyase activity of Escherichia coli K-12. J Bacteriol (1987) 1.42

Class I and III polyhydroxyalkanoate synthases from Ralstonia eutropha and Allochromatium vinosum: characterization and substrate specificity studies. Arch Biochem Biophys (2001) 1.42

Intramolecular regulation of protein tyrosine phosphatase SH-PTP1: a new function for Src homology 2 domains. Biochemistry (1994) 1.41

Lck-dependent tyrosyl phosphorylation of the phosphotyrosine phosphatase SH-PTP1 in murine T cells. Mol Cell Biol (1994) 1.40

Assembly of the Pseudomonas aeruginosa nonribosomal peptide siderophore pyochelin: In vitro reconstitution of aryl-4, 2-bisthiazoline synthetase activity from PchD, PchE, and PchF. Biochemistry (1999) 1.36

Lysine biosynthesis in Saccharomyces cerevisiae: mechanism of alpha-aminoadipate reductase (Lys2) involves posttranslational phosphopantetheinylation by Lys5. Biochemistry (1999) 1.36

Deoxysugars in glycopeptide antibiotics: enzymatic synthesis of TDP-L-epivancosamine in chloroeremomycin biosynthesis. Proc Natl Acad Sci U S A (2000) 1.35