Isomorphous replacement of cystine with selenocystine in endothelin: oxidative refolding, biological and conformational properties of [Sec3,Sec11,Nle7]-endothelin-1.

No abstract is available for this paper.

• Publication year

  1998

• Venue

  Journal of Molecular Biology

• Publication date

  1998-12-04

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1006/JMBI.1998.2189PMID 9826515
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Solution conformation of endothelin and point mutants by nuclear magnetic resonance spectroscopy.

  2009cited by this paper
• Control of peptide disulfide regioisomer formation by mixed cysteine-penicillamine bridges. Application to endothelin-1.

  2009cited by this paper
• Proposed solution structure of endothelin.

  2009cited by this paper
• Solution conformation of endothelin-1 by 1H NMR, CD, and molecular modeling.

  2009cited by this paper
• Determination of the structure of [Nle7]-endothelin by 1H NMR.

  2009cited by this paper
• Synthesis and disulfide structure determination of porcine endothelin: an endothelium-derived vasoconstricting peptide.

  2009cited by this paper
• Solid phase peptide synthesis of human endothelin precursor peptides using two-step hard acid deprotection/cleavage methods.

  2009cited by this paper
• Effects on folding properties of endothelin/apamin by incorporation of selenocysteine into their cysteine framework

  1999cited by this paper
• Atomic mutations in annexin V--thermodynamic studies of isomorphous protein variants.

  1998cited by this paper
• Folding motifs induced and stabilized by distinct cystine frameworks.

  1998cited by this paper
• Formation of native disulfide bonds in endothelin-1. Structural evidence for the involvement of a highly specific salt bridge between the prosequence and the endothelin-1 sequence.

  1998cited by this paper
• The Redox Potential of Selenocystine in Unconstrained Cyclic Peptides

  1997cited by this paper
• Protein folding coupled to disulphide bond formation.

  1997cited by this paper
• Extracting Information from the Temperature Gradients of Polypeptide NH Chemical Shifts. 1. The Importance of Conformational Averaging

  1997cited by this paper
• Chalcogen-analogs of amino acids. Their use in X-ray crystallographic and folding studies of peptides and proteins.

  1997cited by this paper
• Occurrence and Minimization of Cysteine Racemization during Stepwise Solid-Phase Peptide Synthesis(1)(,)(2).

  1997cited by this paper
• Synthesis of selenocysteine peptides and their oxidation to diselenide‐bridged compounds

  1997cited by this paper
• Bioincorporation of telluromethionine into proteins: a promising new approach for X-ray structure analysis of proteins.

  1997cited by this paper
• Protein folding coupled to disulphide bond formation.

  1997cited by this paper
• Oxidative folding of cystine-rich peptides vs regioselective cysteine pairing strategies.

  1996cited by this paper
• Molecular chaperones in cellular protein folding

  1996cited by this paper
• MOLMOL: a program for display and analysis of macromolecular structures.

  1996cited by this paper
• Selenocysteine.

  1996cited by this paper
• Mechanism of reductive protein unfolding

  1995cited by this paper
• Smooth muscle relaxing and hypotensive activities of synthetic calciseptine and the homologous snake venom peptide FS2.

  1995cited by this paper
• High-level biosynthetic substitution of methionine in proteins by its analogs 2-aminohexanoic acid, selenomethionine, telluromethionine and ethionine in Escherichia coli.

  1995cited by this paper
• The formation of protein disulphide bonds.

  1995cited by this paper
• Protein folding: Prolyl isomerases join the fold

  1995cited by this paper
• Synthesis of large peptides in solution

  1995cited by this paper
• D-amino acid scan of endothelin: importance of amino acids adjacent to cysteinyl residues in isomeric selectivity.

  1995cited by this paper
• [Lys(-2)-Arg(-1)]endothelin-1 solution structure by two-dimensional 1H-NMR: possible involvement of electrostatic interactions in native disulfide bridge formation and in biological activity decrease.

  1995cited by this paper
• The solution structure of a monocyclic analogue of endothelin [1,15 Aba]-ET-1, determined by 1H NMR spectroscopy.

  1994cited by this paper
• Redox‐active bis‐cysteinyl peptides. I. Synthesis of cyclic cystinyl peptides by conventional methods in solution and on solid supports

  1994cited by this paper
• The formation of diselenide bridges in proteins by incorporation of selenocysteine residues: biosynthesis and characterization of (Se)2-thioredoxin.

  1994cited by this paper
• The crystal structure of human endothelin

  1994cited by this paper
• Solvent chaperone in protein folding: Selective enhancement of disulfide isomers of endothelin

  1993cited by this paper
• Synthesis and characterization of the selenium analog of glutathione disulfide.

  1993cited by this paper
• Synthetic study on selenocystine-containing peptides.

  1993cited by this paper
• Syntheses and biological activities of selenium analogs of alpha-rat atrial natriuretic peptide.

  1993cited by this paper
• Gradient-Tailored Water Suppression for 1H-15N HSQC Experiments Optimized to Retain Full Sensitivity

  1993cited by this paper
• Gradient-tailored excitation for single-quantum NMR spectroscopy of aqueous solutions

  1992cited by this paper
• Conformational isomerism of endothelin in acidic aqueous media: a quantitative NOESY analysis.

  1992cited by this paper
• Solution structure of endothelin-3 determined using NMR spectroscopy.

  1992cited by this paper
• Conformational study of endothelins and sarafotoxins with the cystine‐stabilized helical motif by means of CD spectra

  1992cited by this paper
• Selenoprotein synthesis: an expansion of the genetic code.

  1991cited by this paper
• The biological activity of endothelin-1 analogues in three different assay systems.

  1991cited by this paper
• The conformation of endothelin-1 in aqueous solution: NMR-derived constraints combined with distance geometry and molecular dynamics calculations.

  1991cited by this paper
• Conformation of endothelin in aqueous ethylene glycol determined by 1H‐NMR and molecular dynamics simulations

  1991cited by this paper
• Factors governing selective formation of specific disulfides in synthetic variants of alpha-conotoxin.

  1991cited by this paper
• Solution conformation of endothelin determined by means of 1H-NMR spectroscopy and distance geometry calculations.

  1991cited by this paper
• An evaluation of computational strategies for use in the determination of protein structure from distance constraints obtained by nuclear magnetic resonance.

  1991cited by this paper
• Structure-activity relationship of endothelin: importance of charged groups.

  1989cited by this paper
• Rapid recording of 2D NMR spectra without phase cycling. Application to the study of hydrogen exchange in proteins

  1989cited by this paper
• A novel potent vasoconstrictor peptide produced by vascular endothelial cells

  1988cited by this paper
• Protein structures from NMR.

  1988cited by this paper
• Determination of three‐dimensional structures of proteins from interproton distance data by dynamical simulated annealing from a random array of atoms Circumventing problems associated with folding

  1988cited by this paper
• Structure and energetics of ligand binding to proteins: Escherichia coli dihydrofolate reductase‐trimethoprim, a drug‐receptor system

  1988cited by this paper
• MLEV-17-based two-dimensional homonuclear magnetization transfer spectroscopy

  1985cited by this paper
• Preparation and Applications of Pentafluorophenyl Esters of 9-Fluorenylmethyloxycarbonyl Amino Acids for Peptide Synthesis

  1983cited by this paper
• A two-dimensional nuclear overhauser experiment with pure absorption phase in four quadrants☆

  1982cited by this paper
• Multiple quantum filters for elucidating NMR coupling networks

  1982cited by this paper
• Synthese von [3,14-L-selenocystein, 8-D-tryptophan]somatostatin

  1980cited by this paper
• Investigation of exchange processes by two‐dimensional NMR spectroscopy

  1979cited by this paper
• A mild procedure for solid phase peptide synthesis: use of fluorenylmethoxycarbonylamino-acids

  1978cited by this paper
• Relative conformational rigidity in oxytocin and (1-penicillamine)-oxytocin: a proposal for the relationship of conformational flexibility to peptide hormone agonism and antagonism.

  1977cited by this paper
• Principles that govern the folding of protein chains.

  1973cited by this paper
• Syntheses and pharmacological properties of selenium isologs of oxytocin and deamino-oxytocin.

  1967cited by this paper
• 6-Hemi-L-selenocystine-oxytocin and 1-deamino-6-hemi-L-selenocystine-oxytocin, highly potent isologs of oxytocin and 1-deamino-oxytocin.

  1965cited by this paper

• Improving chemical synthesis and the antimicrobial activity of human defensins through disulfide bond engineering of HBD-3.

  2025cites this paper
• Directing the oxidative folding of disulfide-rich peptides for enhanced engineering and applications

  2025cites this paper
• Photocatalytic Diselenide Contraction as a Tool for Site‐Selective Isosteric Ubiquitylation

  2025cites this paper
• Biomimetic Folding Strategies for Chemical Synthesis of Disulfide‐Bonded Peptides and Proteins

  2024cites this paper
• Unexpected diselenide metathesis in selenocysteine-substituted biologically active peptides.

  2024cites this paper
• Advances in the synthesis and engineering of conotoxins.

  2024cites this paper
• ER Oxidoreductin 1‐Like Activity of Cyclic Diselenides Drives Protein Disulfide Isomerase in an Electron Relay System

  2024cites this paper
• Selenium intake and multiple health-related outcomes: an umbrella review of meta-analyses

  2023cites this paper
• Design, synthesis, conformational analysis, and biological activity of Cα1-to-Cα6 1,4- and 4,1-disubstituted 1H-[1,2,3]triazol-1-yl-bridged oxytocin analogues

  2023cites this paper
• Se‐Glargine: Chemical Synthesis of a Basal Insulin Analogue Stabilized by an Internal Diselenide Bridge

  2023cites this paper
• Selenium in Peptide Chemistry

  2023cites this paper
• Se-Glargine I. Chemical Synthesis of a Basal Insulin Analog Stabilized by an Internal Diselenide Bridge

  2023cites this paper
• Chemical synthesis of per‐selenocysteine human epidermal growth factor

  2022cites this paper
• Conformational change due to replacement of disulfide with selenosulfide and diselenide in dipeptide vicinal cysteine loop

  2022cites this paper
• Improving Fmoc Solid Phase Synthesis of Human Beta Defensin 3

  2022cites this paper
• Chemical Synthesis of Selenium-containing Peptides.

  2022cites this paper
• Selenium-containing Peptides and their Biological Applications.

  2022cites this paper
• Deciphering Protein Folding Using Chemical Protein Synthesis

  2021cites this paper
• Chemical Synthesis of Selenoproteins

  2021cites this paper
• Flexible Folding: Disulfide-Containing Peptides and Proteins Choose the Pathway Depending on the Environments

  2021influential citation
• Intein-based design expands diversity of selenocysteine reporters.

  2021cites this paper
• Chemical synthesis and biological activity of peptides incorporating an ether bridge as a surrogate for a disulfide bond†

  2020cites this paper
• Chemical synthesis of ferredoxin with 4 selenocysteine residues using a segment condensation method.

  2020cites this paper
• Characterization of (Boc‐Cys/Sec‐NHMe)2 and (Boc‐Cys/Sec‐OMe)2: Evidence of local conformational difference between disulfide and diselenide

  2020cites this paper
• Diselenide crosslinks for enhanced and simplified oxidative protein folding

  2020cites this paper
• α-Conotoxin Peptidomimetics: Probing the Minimal Binding Motif for Effective Analgesia

  2020cites this paper
• A Diaminodiacid (DADA) Strategy for the Development of Disulfide Surrogate Peptides.

  2020cites this paper
• Amino acid chalcogen analogues as tools in peptide and protein research

  2019cites this paper
• Self-assembly of penta-selenopeptides into amyloid fibrils.

  2018cites this paper
• Structure-based development of an osteoprotegerin-like glycopeptide that blocks RANKL/RANK interactions and reduces ovariectomy-induced bone loss in mice.

  2018cites this paper
• Characterization of structural and functional role of selenocysteine in selenoprotein H and its impact on DNA binding

  2018cites this paper
• Dmab/ivDde protected diaminodiacids for solid-phase synthesis of peptide disulfide-bond mimics

  2017cites this paper
• Selen und Selenocystein in der Proteinchemie

  2017cites this paper
• Molecular Engineering of Conus Peptides as Therapeutic Leads.

  2017cites this paper
• Preparation of Selenoinsulin as a Long-Lasting Insulin Analogue.

  2017cites this paper
• Selenium and Selenocysteine in Protein Chemistry.

  2017cites this paper
• Disulfide Bond Mimetics: Strategies and Challenges.

  2017cites this paper
• Chemical Protein Synthesis through Selenocysteine Chemistry

  2017cites this paper
• Cyclisation of Disulfide-Rich Conotoxins in Drug Design Applications

  2016cites this paper
• Stereoselective synthesis and structural elucidation of dicarba peptides.

  2016cites this paper
• Selenium labeling associated with elemental mass spectrometry for receptor-ligand interactions measurement

  2016cites this paper
• The Chemistry of Selenocysteine in Proteins

  2016cites this paper
• Transforming conotoxins into cyclotides: Backbone cyclization of P‐superfamily conotoxins

  2015cites this paper
• Diaminodiacid Bridges to Improve Folding and Tune the Bioactivity of Disulfide-Rich Peptides.

  2015cites this paper
• Probing pattern and dynamics of disulfide bridges using synthesis and NMR of an ion channel blocker peptide toxin with multiple diselenide bonds

  2015cites this paper
• Synthesis and activity of a diselenide bond mimetic of the antimicrobial protein caenopore-5

  2015cites this paper
• Model study using designed selenopeptides on the importance of the catalytic triad for the antioxidative functions of glutathione peroxidase.

  2014cites this paper
• Peptide ligation chemistry at selenol amino acids

  2014cites this paper
• Harnessing selenocysteine reactivity for oxidative protein folding† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c4sc02379j Click here for additional data file.

  2014cites this paper
• A disulfide bond replacement strategy enables the efficient design of artificial therapeutic peptides

  2014cites this paper
• Incorporation of post-translational modified amino acids as an approach to increase both chemical and biological diversity of conotoxins and conopeptides

  2013cites this paper
• Folding of peptides and proteins: role of disulfide bonds, recent developments

  2013cites this paper
• Revealing unexpected mechanisms for nucleophilic attack on S-S and Se-Se bridges.

  2013cites this paper
• Diaminodiacid-based solid-phase synthesis of peptide disulfide bond mimics.

  2013cites this paper
• Tumor-targeted liposomal drug delivery mediated by a diseleno bond-stabilized cyclic peptide

  2013cites this paper
• Incorporation of post-translational modified amino acids as an approach to increase both chemical and biological diversity of conotoxins and conopeptides

  2013cites this paper
• Synthesis and application of a Sec2-containing oligopeptide for method evaluation purposes in selenium speciation.

  2012cites this paper
• Selenenylsulfide-linked homogeneous glycopeptides and glycoproteins: synthesis of human "hepatic Se metabolite A".

  2012cites this paper
• Strategic use of non-native diselenide bridges to steer oxidative protein folding.

  2012cites this paper
• Dissecting a role of evolutionary‐conserved but noncritical disulfide bridges in cysteine‐rich peptides using ω‐conotoxin GVIA and its selenocysteine analogs

  2012cites this paper
• The Chemistry of Selenocysteine

  2011cites this paper
• Total synthesis of the analgesic conotoxin MrVIB through selenocysteine-assisted folding.

  2011cites this paper
• Selenopeptide Analogs of EETI‐II Retain Potent Trypsin Inhibitory Activities

  2011cites this paper
• α-Conotoxin ImI incorporating stable cystathionine bridges maintains full potency and identical three-dimensional structure.

  2011cites this paper
• Selenium compounds are substrates for glutaredoxins: a novel pathway for selenium metabolism and a potential mechanism for selenium-mediated cytotoxicity.

  2010cites this paper
• Diselenium, instead of disulfide, bonded analogs of conotoxins: novel synthesis and pharmacotherapeutic potential.

  2010cites this paper
• Disulfide-Depleted Selenoconopeptides: a Minimalist Strategy to Oxidative Folding of Cysteine-Rich Peptides.

  2010cites this paper
• Solving the alpha-conotoxin folding problem: efficient selenium-directed on-resin generation of more potent and stable nicotinic acetylcholine receptor antagonists.

  2010cites this paper
• Disulfide-Depleted Selenoconopeptides: Simplified Oxidative Folding of Cysteine-Rich Peptides

  2010cites this paper
• Site-specific effects of diselenide bridges on the oxidative folding of a cystine knot peptide, omega-selenoconotoxin GVIA.

  2010cites this paper
• NMR methods for determining disulfide-bond connectivities.

  2010cites this paper
• Modulating oxytocin activity and plasma stability by disulfide bond engineering.

  2010cites this paper
• Probing the role of the proximal heme ligand in cytochrome P450cam by recombinant incorporation of selenocysteine

  2009cites this paper
• Direct visualization of disulfide bonds through diselenide proxies using 77Se NMR spectroscopy.

  2009cites this paper
• Integrated oxidative folding of cysteine/selenocysteine containing peptides: improving chemical synthesis of conotoxins.

  2009cites this paper
• Selenoglutaredoxin as a Glutathione Peroxidase Mimic

  2008cites this paper
• Synthesis of Selenocysteine and Selenomethionine Derivatives from Sulfur‐Containing Amino Acids

  2008cites this paper
• Folding of Conotoxins: Formation of the Native Disulfide Bridges During Chemical Synthesis and Biosynthesis of Conus Peptides

  2008cites this paper
• Selenopeptide chemistry

  2008cites this paper
• The synthesis of 1-thia-6-oxa-6aλ4-seleno-3-azapentalene and a 3H-1,2,4-dithiazole

  2007cites this paper
• Selenoglutathione: efficient oxidative protein folding by a diselenide.

  2007cites this paper
• Chemical modification of conotoxins to improve stability and activity.

  2007cites this paper
• The synthesis of 1-thia-6-oxa-6alambda(4)-seleno-3-azapentalene and a 3H-1,2,4-dithiazole.

  2007cites this paper
• Biotechnology of selenocysteine

  2006cites this paper
• Alpha-selenoconotoxins, a new class of potent alpha7 neuronal nicotinic receptor antagonists.

  2006cites this paper
• Synthesis of selenocystine derivatives from cystine by applying the transformation reaction from disulfides to diselenides

  2006cites this paper
• α-Selenoconotoxins, a New Class of Potent α7 Neuronal Nicotinic Receptor Antagonists*

  2006cites this paper
• Conotoxins as research tools and drug leads.

  2005cites this paper
• Isosteric replacement of sulfur with other chalcogens in peptides and proteins

  2005cites this paper
• Identification et caracterisation des Glutaredoxines de la cyanobacterie Synechocystis

  2005cites this paper
• Synthesis of single‐ and multiple‐stranded cystine‐rich peptides

  2005cites this paper
• Selenocysteine in proteins-properties and biotechnological use.

  2005cites this paper
• Selenomethionine and selenocysteine double labeling strategy for crystallographic phasing.

  2003cites this paper
• Selenocysteine Derivatives for Chemoselective Ligations

  2002cites this paper
• Chemistry of biologically important synthetic organoselenium compounds.

  2001cites this paper
• Selenocysteine in native chemical ligation and expressed protein ligation.

  2001cites this paper
• Synthesis and conformational analysis of apamin analogues with natural and non-natural cystine/selenocystine connectivities.

  2000cites this paper
• The disulfide‐coupled folding pathway of apamin as derived from diselenide‐quenched analogs and intermediates

  1999cites this paper
• Selenium metabolism, selenoproteins and mechanisms of cancer prevention: complexities with thioredoxin reductase.

  1999cites this paper