Transition-state stabilization at the oxyanion binding sites of serine and thiol proteinases: hydrolyses of thiono and oxygen esters.

No abstract is available for this paper.

• Publication year

  1983

• Venue

  Biochemistry

• Publication date

  1983-01-04

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/BI00270A017PMID 6338911
• 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.

• Stereochemical aspects of peptide hydrolysis catalyzed by serine proteases of the chymotrypsin type

  1981cited by this paper
• Isolation of highly active papaya peptidases A and B from commercial chymopapain.

  1981cited by this paper
• Computation of peptide-protein interactions. Catalysis by chymotrypsin: prediction of relative substrate reactivities

  1981cited by this paper
• An X-ray crystallographic approach to enzyme structure and function.

  1980cited by this paper
• The question of differential hydrogen bonding in the mechanism of catalysis by serine proteases

  1978cited by this paper
• Catalysis and leaving group binding in anilide hydrolysis by chymotrypsin.

  1978cited by this paper
• Binding of chloromethyl ketone substrate analogues to crystalline papain.

  1977cited by this paper
• Serine proteases: structure and mechanism of catalysis.

  1977cited by this paper
• On the enhanced catalytic activity of papain towards amide substrates.

  1977cited by this paper
• HYDROLYSIS OF IMIDATE SALTS STEREOELECTRONIC CONTROL IN THE CLEAVAGE OF THE HEMIORTHOAMIDE TETRAHEDRAL INTERMEDIATE

  1975cited by this paper
• The importance of the conformation of the tetrahedral intermediate for the α‐chymotrypsin‐catalyzed hydrolysis of peptide substrates

  1975cited by this paper
• The importance of the conformation of the tetrahedral intermediate for the alpha-chymotrypsin-catalyzed hydrolysis of peptide substrates.

  1975cited by this paper
• On the stereochemistry of catalysis by serine proteases.

  1974cited by this paper
• A dithioamino acid in kinetic studies on trypsin catalysis. The tryptic S-alkyl cleavage of ethyl 6-ammoniumdithiohexanoate p-toluene sulfonate.

  1974cited by this paper
• On the mode of activation of the catalytically essential sulfhydryl group of papain.

  1973cited by this paper
• Leaving group specificity in the chymotrypsin-catalyzed hydrolysis of peptides. A stereochemical interpretation.

  1973cited by this paper
• Intramolecular catalysis and the involvement of tetrahedral intermediate partitioning in the hydrolysis of benzoylcholine, benzoylthionocholine, and their dimethylamino analogs

  1973cited by this paper
• Subtilisin; a stereochemical mechanism involving transition-state stabilization.

  1972cited by this paper
• On the role of hydrogen-bonding system in the catalysis by serine proteases.

  1972cited by this paper
• Symmetry and asymmetry in the mechanisms of hydrolysis by serine proteases and their thiol analogues.

  1972cited by this paper
• Kinetic specificity in papain-catalysed hydrolyses.

  1971cited by this paper
• Determination of the individual rate constants of α‐chymotrypsin‐catalyzed hydrolysis with the added nucleophilic agent, 1,4‐butanediol

  1971cited by this paper
• Structure of crystalline alpha-chymotrypsin. IV. The structure of indoleacryloyl-alpha-chyotrypsin and its relevance to the hydrolytic mechanism of the enzyme.

  1970cited by this paper
• Chymotrypsin-catalyzed phenyl ester hydrolysis. Evidence for electrophilic assistance on carbonyl oxygen.

  1970cited by this paper
• An agarose mercurial column for the separation of mercaptopapain and nonmercaptopapain.

  1970cited by this paper
• The determination of the concentration of hydrolytic enzyme solutions: alpha-chymotrypsin, trypsin, papain, elastase, subtilisin, and acetylcholinesterase.

  1966cited by this paper
• The amino acid sequence around the reactive thiol group of chymopapain B.

  1966cited by this paper
• DIRECT EVIDENCE FOR AN ACYLATED THIOL AS AN INTERMEDIATE IN PAPAIN- AND FICIN-CATALYSED HYDROLYSES.

  1965cited by this paper
• MECHANISM OF ACTION OF PROTEOLYTIC ENZYMES.

  1965cited by this paper
• Kinetic Evidence for the Formation of Acyl-Enzyme Intermediates in the -Chymotrypsin-Catalyzed Hydrolyses of Specific Substrates

  1964cited by this paper
• Nitriles and Amidines of Optically Active Acylamino Acids and Peptides

  1963cited by this paper
• The Kinetics of the Acidic and Alkaline Hydrolysis of Ethyl Thionbenzoate

  1963cited by this paper
• Herstellung von α‐Aminosäureestern durch Alkoholyse der Methylester

  1953cited by this paper
• The Kinetics of the α-Chymotrypsin-Catalyzed Hydrolysis of Acetyl- and Nicotinyl-L-phenylalaninamide in Aqueous Solutions at 25° and pH 7.91

  1951cited by this paper
• THE INHIBITION OF ARGINASE BY AMINO ACIDS

  1945cited by this paper

• Thioamide Analogues of MHC I Antigen Peptides.

  2023cites this paper
• Rational design of thioamide peptides as selective inhibitors of cysteine protease cathepsin L

  2021cites this paper
• Exploring the Catalytic Reaction of Cysteine Proteases.

  2020cites this paper
• Studies of Thioamide Effects on Serine Protease Activity Enable Two-Site Stabilization of Cancer Imaging Peptides.

  2020cites this paper
• Rosetta Machine Learning Models Accurately Classify Positional Effects of Thioamides on Proteolysis.

  2020cites this paper
• The reaction mechanism of Zika virus NS2B/NS3 serine protease inhibition by dipeptidyl aldehyde: a QM/MM study.

  2019cites this paper
• Fluorescent Probes for Studying Thioamide Positional Effects on Proteolysis Reveal Insight into Resistance to Cysteine Proteases

  2019cites this paper
• Kinetic, Mutational, and Structural Studies of the Venezuelan Equine Encephalitis Virus Nonstructural Protein 2 Cysteine Protease.

  2016cites this paper
• Quantifying tetrahedral adduct formation and stabilization in the cysteine and the serine proteases

  2015cites this paper
• Catalytic Mechanisms of Serine and Threonine Peptidases

  2013cites this paper
• Catalytic Mechanisms of Cysteine Peptidases

  2013cites this paper
• Quantum Mechanical Modeling: A Tool for the Understanding of Enzyme Reactions

  2013cites this paper
• Removing allosteric feedback inhibition of tomato 4-coumarate:CoA ligase by directed evolution.

  2012cites this paper
• Crystallographic evidence for active-site dynamics in the hydrolytic aldehyde dehydrogenases. Implications for the deacylation step of the catalyzed reaction.

  2011cites this paper
• Looking at the proteases from a simple perspective

  2011cites this paper
• Minimal transition state charge stabilization of the oxyanion during peptide bond formation by the ribosome.

  2011cites this paper
• Hydration of acetone in the gas phase and in water solvent

  2010cites this paper
• Elucidation of menaquinone biosynthesis in Escherichia coli and explorative investigation of protein organization in the pathway

  2008cites this paper
• Substrate‐ and pH‐dependent contribution of oxyanion binding site to the catalysis of prolyl oligopeptidase, a paradigm of the serine oligopeptidase family

  2008cites this paper
• Determination of the structure of tetrahedral transition state analogues bound at the active site of chymotrypsin using 18O and 2H isotope shifts in the 13C NMR spectra of glyoxal inhibitors.

  2007cites this paper
• Nonpolar and short side chain groups at C-11beta of estradiol result in antiestrogens.

  2005cites this paper
• Interaction of papain-like cysteine proteases with dipeptide-derived nitriles.

  2005cites this paper
• The catalytic triad of serine peptidases

  2005cites this paper
• A Comparison of Staphostatin B with Standard Mechanism Serine Protease Inhibitors*

  2005cites this paper
• Acyl-CoA dehydrogenases. A mechanistic overview.

  2004cites this paper
• Tyrosine 547 Constitutes an Essential Part of the Catalytic Mechanism of Dipeptidyl Peptidase IV*

  2004cites this paper
• A mechanistic overview

  2004cites this paper
• Electrostatic Effects and Binding Determinants in the Catalysis of Prolyl Oligopeptidase

  2002cites this paper
• Role of the oxyanion binding site and subsites S1 and S2 in the catalysis of oligopeptidase B, a novel target for antimicrobial chemotherapy.

  2002cites this paper
• Transferring Groups by Displacement Reactions

  2001cites this paper
• The role of a β-proton transfer donor in the degradation of benzylpenicillin

  2001cites this paper
• Studies with Potential Reporter Group Reagents for Enzymes: 3,4-Dihydro-3-(2-Hydroxyethyl)-6-Nitro-2H-1,3-Benzothiazin-2-Thione and 6-Nitrochromone—Hydrolysis and Interaction with Chymotrypsin

  2000cites this paper
• The Oxyanion Hole in Serine beta-Lactamase Catalysis: Interactions of Thiono Substrates with the Active Site.

  2000cites this paper
• The crystal structure of pyroglutamyl peptidase I from Bacillus amyloliquefaciens reveals a new structure for a cysteine protease.

  1999cites this paper
• Using NMR as a probe of protein structure and function.

  1999cites this paper
• Conservative Electrostatic Potential Patterns at Enzyme Active Sites: The Anion-Cation-Anion Triad

  1999cites this paper
• Oligopeptidase B: a new type of serine peptidase with a unique substrate-dependent temperature sensitivity.

  1999cites this paper
• The role of threonine in the P2 position of Bowman-Birk proteinase inhibitors: studies on P2 variation in cyclic peptides encompassing the reactive site loop.

  1998cites this paper
• Antibody-Catalysed Peptide Nitroanilide Hydrolysis Using a new type of Hapten

  1998cites this paper
• The urease-catalyzed hydrolysis of thiourea and thioacetamide.

  1998cites this paper
• A 13C-NMR study of the role of Asn-155 in stabilizing the oxyanion of a subtilisin tetrahedral adduct.

  1997cites this paper
• Probing substrate backbone function in prolyl oligopeptidase catalysis--large positional effects of peptide bond monothioxylation.

  1997cites this paper
• Review: Endothiopeptides Alias Peptide Thioamides

  1997cites this paper
• Desilylative elimination of the quinazolinone ring from 1-(4-oxoquinazolin-3-yl)-2-silylaziridines; preparation of an N–H aziridine in high enantiomeric excess by in situ nucleophilic addition to the derived azirine

  1997cites this paper
• Discussion of the catalytic pathway of cysteine proteases based on AM1 calculations

  1997cites this paper
• Small synthetic inhibitors of cysteine proteases

  1996cites this paper
• Molecular modeling of substrate-enzyme reactions for the cysteine protease papain.

  1996cites this paper
• Preparation of N–H azirdines in high enantiomeric excess by in situ aziridine–azirine–aziridine interconversion

  1996cites this paper
• Extremely mild reagent for Boc deprotection applicable to the synthesis of peptides with thioamide linkages

  1996cites this paper
• Effects of ligand homologation and ligand reactivity on the apparent kinetic specificity of papain.

  1995cites this paper
• Enhanced alkaline hydrolysis of monoesterified 4-tert-butylcalix[4]arenes involving intramolecular electrophilic catalysis by the phenolic hydroxy group

  1994cites this paper
• Peptidyl thioamides as substrates and inhibitors of papain, and as probes of the kinetic significance of the oxyanion hole.

  1994cites this paper
• Influence on proline-specific enzymes of a substrate containing the thioxoaminoacyl-prolyl peptide bond.

  1994cites this paper
• X‐ray crystallographic structure of a papain‐leupeptin complex

  1993cites this paper
• Prolyl oligopeptidase catalysis Reactions with thiono substrates reveal substrate‐induced conformational change to be the rate‐limiting step

  1993cites this paper
• The contribution of intermolecular hydrogen bonding to the kinetic specificity of papain.

  1993cites this paper
• A study of the stabilization of tetrahedral adducts by trypsin and delta-chymotrypsin.

  1992cites this paper
• Quantitative structure-activity analysis of acetylcholinesterase inhibition by oxono and thiono analogues of organophosphorus compounds.

  1992cites this paper
• Effect of side-chain amide thionation on turnover of beta-lactam substrates by beta-lactamases. Further evidence on the question of side-chain hydrogen-bonding in catalysis.

  1992cites this paper
• Oxyanion hole interactions in serine and cysteine proteases.

  1992cites this paper
• Reversible binding of peptide aldehydes to papain. Structure-activity relationships.

  1991cites this paper
• Removal of an inter-domain hydrogen bond through site-directed mutagenesis: role of serine 176 in the mechanism of papain.

  1991cites this paper
• Contribution of the glutamine 19 side chain to transition-state stabilization in the oxyanion hole of papain.

  1991cites this paper
• Synthesis of Thioesters and Thiolactones

  1991cites this paper
• Cysteinyl proteinases and their selective inactivation.

  1990cites this paper
• Synergism between stereoelectronic and stereoprotonic effects in the enzymic peptide bond formation

  1990cites this paper
• Some remarkable effects of thiopeptide and derived linkages on lysozyme release from neutrophils by esters of the chemotactic peptide N-formyl-methionyl-leucyl-phenylalanine (f-Met-Leu-Phe-OR).

  1989cites this paper
• A 13C-n.m.r. investigation of the ionizations within an inhibitor--alpha-chymotrypsin complex. Evidence that both alpha-chymotrypsin and trypsin stabilize a hemiketal oxyanion by similar mechanisms.

  1989cites this paper
• Electrostatic catalysis in enzymes

  1988cites this paper
• Consequences of molecular recognition in the S1-S2 intersubsite region of papain for catalytic-site chemistry. Change in pH-dependence characteristics and generation of an inverse solvent kinetic isotope effect by introduction of a P1-P2 amide bond into a two-protonic-state reactivity probe.

  1988cites this paper
• The Principle of Least Nuclear Motion and the Theory of Stereoelectronic Control

  1988cites this paper
• Mechanism of proline-specific proteinases: (I) Substrate specificity of dipeptidyl peptidase IV from pig kidney and proline-specific endopeptidase from Flavobacterium meningosepticum.

  1988cites this paper
• Coenzyme A dithioesters: synthesis, characterization and reaction with citrate synthase and acetyl-CoA:choline O-acetyltransferase.

  1988cites this paper
• Trypsin hydrolysis of X-phenyl hippurates.

  1988cites this paper
• Evidence for an oxyanion hole in serine beta-lactamases and DD-peptidases.

  1988cites this paper
• Cysteine proteases: The S2P2 hydrogen bond is more important for catalysis than is the analogous S1P1 bond

  1988cites this paper
• Synthesis of fluorescent peptidyl thioneamides and the assay of papain in the presence of trypsin.

  1987cites this paper
• Chapter 3 Structure and function of serine proteases

  1987cites this paper
• Chapter 2 Cysteine proteinases

  1987cites this paper
• Carboxyl-modified amino acids and peptides as protease inhibitors.

  1986cites this paper
• The basic difference in catalyses by serine and cysteine proteinases resides in charge stabilization in the transition state.

  1986cites this paper
• Net-charge models in the analysis of ion and electron transfer in enzyme reactions.

  1986cites this paper
• 13C NMR study of the stereospecificity of the thiohemiacetals formed on inhibition of papain by specific enantiomeric aldehydes.

  1986cites this paper
• 13C NMR of enzymes

  1985cites this paper
• A 13C-n.m.r. investigation of ionizations within a trypsin-inhibitor complex. Evidence that the pKa of histidine-57 is raised by interaction with the hemiketal oxyanion.

  1985cites this paper
• Comparison of the kinetics and mechanism of the papain-catalyzed hydrolysis of esters and thiono esters.

  1985cites this paper
• The design and properties of N-carboxyalkyldipeptide inhibitors of angiotensin-converting enzyme.

  1985cites this paper
• 13C NMR study of the ionizations within a trypsin-chloromethyl ketone inhibitor complex.

  1985cites this paper
• Mechanism of action of cysteine proteinases: oxyanion binding site is not essential in the hydrolysis of specific substrates.

  1985cites this paper
• Stereochemical analysis of peptide bond hydrolysis catalyzed by the aspartic proteinase penicillopepsin.

  1985cites this paper
• [Thermitase--a thermostable serine protease. IV. Kinetic studies on the binding of N-acyl peptide ketones as substrate analog inhibitors].

  1984cites this paper
• An interactive computer graphics study of thermolysin-catalyzed peptide cleavage and inhibition by N-carboxymethyl dipeptides.

  1984cites this paper
• Role of catalytic residues in the formation of a tetrahedral adduct in the acylation reaction of bovine beta-trypsin. A molecular orbital study.

  1984cites this paper
• A re-evaluation of the nomenclature of the cysteine proteinases of Carica papaya and a rational basis for their identification.

  1983cites this paper
• Purification and characterization of a novel proteinase, chymopapain S

  1983cites this paper