Papain hydrolysis of X-phenyl-N-methanesulfonyl glycinates: a quantitative structure-activity relationship and molecular graphics analysis.

Abstract:

:The hydrolysis of 32 X-phenyl-N-methanesulfonyl glycinates by papain was investigated. It was found that the variation in the Michaelis constants could be rationalized by the following correlation equation: log 1/Km = 0.61 pi '3 + 0.46 MR4 + 0.55 sigma + 2.00 with a correlation coefficient of 0.945. In this expression, pi '3 is the hydrophobic constant for the more lipophilic of the two possible meta substituents, MR4 is the molar refractivity of 4-substituents, and sigma is the Hammett constant summed for all substituents. Using this equation, we designed, synthesized, and successfully predicted Km for a new congener intended to maximize binding (1/Km). The interactions involved in enzyme-substrate binding, as characterized by the correlation equation, are interpreted using a computer-constructed color three-dimensional-graphics molecular model of the enzyme active site. The nonenzymatic hydrolysis (both acid and basic) of phenyl hippurates yield rate constants which are well correlated by Hammett equations; however, log k for both acid and alkaline hydrolysis are not linearly related to log 1/Km or log kcat/Km.

journal_name

Arch Biochem Biophys

authors

Carotti A,Smith RN,Wong S,Hansch C,Blaney JM,Langridge R

doi

10.1016/0003-9861(84)90136-x

subject

Has Abstract

pub_date

1984-02-15 00:00:00

pages

112-25

issue

1

eissn

0003-9861

issn

1096-0384

pii

0003-9861(84)90136-X

journal_volume

229

pub_type

杂志文章
  • On the stability of the extracellular hemoglobin of Glossoscolex paulistus, in two iron oxidation states, in the presence of urea.

    abstract::The stability of the Glossoscolex paulistus hemoglobin (HbGp), in two iron oxidation states (and three forms), as monitored by optical absorption, fluorescence emission and circular dichroism (CD) spectroscopies, in the presence of the chaotropic agent urea, is studied. HbGp oligomeric dissociation, denaturation and i...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/j.abb.2012.01.007

    authors: Carvalho FA,Santiago PS,Tabak M

    更新日期:2012-03-01 00:00:00

  • Identification of a new tetrameric pyridoxal 4-dehydrogenase as the second enzyme in the degradation pathway for pyridoxine in a nitrogen-fixing symbiotic bacterium, Mesorhizobium loti.

    abstract::We have found for the first time that a chromosomal gene, mlr6807, in Mesorhizobium loti encodes a new tetrameric pyridoxal 4-dehydrogenase (PLDH). The recombinant enzyme expressed in Escherichia coli cells was homogenously purified and characterized. The enzyme consisted of four subunits each with a molecular weight ...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/j.abb.2006.06.002

    authors: Yokochi N,Nishimura S,Yoshikane Y,Ohnishi K,Yagi T

    更新日期:2006-08-01 00:00:00

  • The voltage dependent anion channel affects mitochondrial cholesterol distribution and function.

    abstract::We have observed abnormally high membrane cholesterol levels and a subsequent deficiency of oxidative energy production in mitochondria from cultured Morris hepatoma cells (MH7777). Using cholesterol affinity chromatography and MALDI-TOF Mass Spectrometry, we have identified the voltage dependent anion channel (VDAC) ...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/j.abb.2007.06.012

    authors: Campbell AM,Chan SH

    更新日期:2007-10-15 00:00:00

  • Quantification of cysteine sulfinic acid decarboxylase in male and female rats: effect of adrenalectomy and methionine.

    abstract::Hepatic cysteine sulfinic acid decarboxylase (EC 4.1.1.29) activity has been reported to decrease in response to both L-methionine (Met) feeding and adrenalectomy in rats. A series of experiments was conducted to (a) determine if CSAD depression was evident in female rats fed a methionine-supplemented diet; and (b) de...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/0003-9861(92)90721-8

    authors: Jerkins AA,Steele RD

    更新日期:1992-05-01 00:00:00

  • Regulation of the plasma membrane type III phosphatidylinositol 4-kinase by positively charged compounds.

    abstract::The effects of positively charged compounds on a plasma membrane, type III phosphatidylinositol 4-kinase were studied. To determine whether the enzyme would respond differently to the compounds in a membrane-associated versus a soluble state, both the plasma membrane and solubilized (released by 0.01% (v/v) Triton X-1...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1006/abbi.1994.1366

    authors: Yang W,Boss WF

    更新日期:1994-08-15 00:00:00

  • Investigation of the substrate structure and metal cofactor requirements of the rat liver mitochondrial ATP synthase/ATPase complex.

    abstract::The F1 moiety of the rat liver mitochondrial ATP synthase/ATPase complex contains as isolated 2 mol Mg2+/mol F1, 1 mol of which is nonexchangeable and the other which is exchangeable (N. Williams, J. Hullihen, and P.L. Pedersen, (1987) Biochemistry 26, 162-169). In addition, the enzyme binds 1 mol ADP/mol F1 and 3 mol...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/0003-9861(89)90571-7

    authors: Hanley-Trawick S,Carpen ME,Dunaway-Mariano D,Pedersen PL,Hullihen J

    更新日期:1989-01-01 00:00:00

  • Reductant-independent ATP hydrolysis catalyzed by homologous nitrogenase proteins from Azotobacter vinelandii and heterologous crosses with Clostridium pasteuranium.

    abstract::Reductant-independent ATPase activity was initiated and studied for Azotobacter vinelandii and Clostridium pasteuranium nitrogenase proteins (Av1, Cp1 and Av2, Cp2, 1 designating the iron molybdenum protein and 2 the iron protein) and their heterologous crosses by two methods: (1) allowing dithionite to be depleted fr...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1006/abbi.1995.9972

    authors: Larsen C,Christensen S,Watt GD

    更新日期:1995-11-10 00:00:00

  • Regulation by forskolin of octopamine-stimulated adenylate cyclase from brain of the dipterous Ceratitis capitata.

    abstract::Forskolin, a diterpene that exerts several pharmacological effects, activates adenylate cyclase in brain and in some other mammalian tissues. Properties of forskolin activation of adenylate cyclase from central nervous system of the dipterous Ceratitis capitata are described. The interaction of forskolin with the inse...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/0003-9861(87)90099-3

    authors: Guillen A,Haro A,Municio AM

    更新日期:1987-04-01 00:00:00

  • Isolation and characterization of human liver cytochrome P450 2C19: correlation between 2C19 and S-mephenytoin 4'-hydroxylation.

    abstract::In an effort to identify and characterize minor forms of human liver cytochrome P450, immunoblot analyses of microsome samples were developed with antibodies to various P450s that recognized multiple human P450s. Four P450s were recognized in immunoblot analyses of human liver microsome samples developed with an antib...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1006/abbi.1993.1506

    authors: Wrighton SA,Stevens JC,Becker GW,VandenBranden M

    更新日期:1993-10-01 00:00:00

  • Hypochlorite-modified high-density lipoprotein promotes induction of HO-1 in endothelial cells via activation of p42/44 MAPK and zinc finger transcription factor Egr-1.

    abstract::Modification/chlorination of high-density lipoprotein (HDL) by hypochlorous acid (HOCl), formed by the myeloperoxidase-H₂O₂-chloride system of activated phagocytes, converts an anti-atherogenic lipoprotein into a pro-inflammatory lipoprotein particle. Chlorinated HDL is present in human lesion material, binds to and i...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/j.abb.2011.02.016

    authors: Rossmann C,Rauh A,Hammer A,Windischhofer W,Zirkl S,Sattler W,Malle E

    更新日期:2011-05-01 00:00:00

  • The pH dependence of the kinetic parameters of ketol acid reductoisomerase indicates a proton shuttle mechanism for alkyl migration.

    abstract::The enzyme ketol acid reductoisomerase catalyzes the second common reaction in the biosynthesis of the branched chain amino acids. The reaction is complex as an alkyl migration and a ketone reduction apparently occur as separate steps during the conversion of acetolactate to 2,3-dihydroxy-3-methylbutyrate. This paper ...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/0003-9861(92)90710-e

    authors: Mrachko GT,Chunduru SK,Calvo KC

    更新日期:1992-05-01 00:00:00

  • Characterization of the subunits of beta-conglycinin.

    abstract::Four subunits of beta-conglycinin were purified from soybean cultivar CX 635-1-1-1, and were designated alpha, alpha', beta, and beta' in accordance with nomenclature proposed by Thanh and Shibasaki [(1977) Biochim. Biophys. Acta 490, 370-384]. Of these subunits, beta' has not previously been reported or characterized...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/0003-9861(85)90787-8

    authors: Coates JB,Medeiros JS,Thanh VH,Nielsen NC

    更新日期:1985-11-15 00:00:00

  • Investigating interaction of ligands with voltage dependent anion channel through noise analyses.

    abstract::Ion channel-protein complexes inserted in the membrane act as molecular gates for transport across the membrane. The opening and closing of these gates can be controlled by one or more variables like ligands (small molecules, proteins, etc.), transmembrane voltage, and the concentration gradient of a chemical across t...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/j.abb.2004.12.019

    authors: Banerjee J,Ghosh S

    更新日期:2005-03-15 00:00:00

  • Losartan, an antagonist of AT1 receptor for angiotensin II, attenuates lipopolysaccharide-induced acute lung injury in rat.

    abstract::Angiotensin II (Ang II) plays an important role in inflammatory process. Acute lung injury (ALI), an inflammatory disorder of the lung, is commonly associated with endotoxemia; however, the mechanism that endotoxin (lipopolysaccharide, LPS) induces the inflammatory response in ALI is not well defined. Here, we showed,...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/j.abb.2008.09.019

    authors: Liu L,Qiu HB,Yang Y,Wang L,Ding HM,Li HP

    更新日期:2009-01-01 00:00:00

  • Cardiac transcription factor Nkx2.5 interacts with p53 and modulates its activity.

    abstract::Transcription factor Nkx2.5, essential for heart development, regulates cardiomyocyte-specific gene expression through combinatorial interactions with other cardiac-restricted (GATA4 and dHAND) or ubiquitous (p300) transcription regulators. Here we demonstrate that Nkx2.5 and p53 synergistically activate the promoter ...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/j.abb.2015.02.001

    authors: Kojic S,Nestorovic A,Rakicevic L,Protic O,Jasnic-Savovic J,Faulkner G,Radojkovic D

    更新日期:2015-03-01 00:00:00

  • Fe-heme structure in Cu, Zn superoxide dismutase from Haemophilus ducreyi by X-ray absorption spectroscopy.

    abstract::We have carried out an X-ray Absorption Spectroscopy (XAS) study of ferric, ferrous, CO- and NO-bound Haemophilus ducreyi Cu,ZnSOD (HdSOD) in solution to investigate the structural modifications induced by the binding of small gaseous ligands to heme in this enzyme. The combined analysis of EXAFS and XANES data has al...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/j.abb.2010.03.010

    authors: D'Angelo P,Zitolo A,Pacello F,Mancini G,Proux O,Hazemann JL,Desideri A,Battistoni A

    更新日期:2010-06-01 00:00:00

  • Effect of training on H(2)O(2) release by mitochondria from rat skeletal muscle.

    abstract::In this study, oxygen consumption and H(2)O(2) release rate by succinate or pyruvate/malate supplemented mitochondria isolated from skeletal muscle of trained and untrained rats were investigated. The overall mitochondrial antioxidant capacity and the effect of preincubation of mitochondria with GDP, an inhibitor of u...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1006/abbi.1999.1494

    authors: Venditti P,Masullo P,Di Meo S

    更新日期:1999-12-15 00:00:00

  • Expression and processing of a bacterial endoglucanase in transgenic mice.

    abstract::The C6.5 endoglucanase from Bacillus subtilis catalyzes the hydrolyses of beta-glucans. This enzyme, which is also produced by many ruminant microbes, is not part of the normal digestive repertoire of monogastric animals. We have generated transgenic mice which express the C6.5 endoglucanase gene specifically in the p...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1006/abbi.1999.1243

    authors: Zhang JX,Meidinger R,Forsberg CW,Krell PJ,Phillips JP

    更新日期:1999-07-15 00:00:00

  • Modes of inhibitory action of 4 beta-phorbol 12-myristate 13-acetate in thrombin-stimulated arachidonic acid release in intact and permeabilized platelets.

    abstract::The tumor-promoting phorbol ester 4 beta-phorbol 12-myristate 13-acetate (PMA) inhibited thrombin-stimulated arachidonic acid (AA) release in rabbit and human platelets. PMA was effective over the same concentration range that activates protein kinase C in intact rabbit platelets: IC50 vs thrombin = 0.5 nM, greater th...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/0003-9861(90)90021-p

    authors: Murayama T,Kajiyama Y,Takahashi A,Nomura Y

    更新日期:1990-01-01 00:00:00

  • Effect of ethanol on tropomyosin in solution and in reconstituted thin filaments.

    abstract::The effects of ethanol at concentrations below 10% on the conformation of tropomyosin, its end-to-end polymerization, its binding to F-actin, and its effects on actomyosin ATPase activity were studied. Ethanol stabilized the tropomyosin conformation by shifting the helix thermal unfolding profile to higher temperature...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/0003-9861(86)90333-4

    authors: Ishii Y,Lehrer SS,Ohnishi ST,Rubin E

    更新日期:1986-05-01 00:00:00

  • Free fatty acid effects on mitochondrial permeability: an overview.

    abstract::A variety of experimental conditions elicit increases in mitochondrial permeability that can be differentiated from the classic cyclosporin A (CsA)-sensitive mitochondrial permeability transition (MPT). For example, butylated hydroxytoluene, signal peptides, and the hormone thyroxine have been shown to promote increas...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1006/abbi.2000.2195

    authors: Sultan A,Sokolove PM

    更新日期:2001-02-01 00:00:00

  • Role of protein -SH groups in redox homeostasis--the erythrocyte as a model system.

    abstract::The reactivities of the sulfhydryl groups of rat, turkey, human, and calf hemoglobin were studied together with the enzyme activities of glutathione peroxidase, glutathione reductase, glucose-6-phosphate dehydrogenase, and glutaredoxin in lysed erythrocytes to evaluate their roles in regulating redox homeostasis. The ...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1006/abbi.1998.0694

    authors: Di Simplicio P,Cacace MG,Lusini L,Giannerini F,Giustarini D,Rossi R

    更新日期:1998-07-15 00:00:00

  • Modification of an essential amino group of phosphoenolpyruvate carboxylase from maize leaves by pyridoxal phosphate and by pyridoxal phosphate-sensitized photooxidation.

    abstract::Phosphoenolpyruvate carboxylase from maize leaves was inactivated by pyridoxal 5'-phosphate in the dark and in the light. A two-step reversible mechanism is proposed for inactivation in the dark, which involves the formation of a noncovalent complex prior to a Schiff base with amino groups of the enzyme. Spectral anal...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/0003-9861(86)90309-7

    authors: Podesta FE,Iglesias AA,Andreo CS

    更新日期:1986-05-01 00:00:00

  • Fusion of sperm with prostasomes: effects on membrane fluidity.

    abstract::Prostasomes are membranous vesicles (150-200 nm diameter) present in human semen. They are secreted by the prostate gland and contain large amounts of cholesterol, sphingomyelin, and Ca2+. In addition, some of their proteins are enzymes. Prostasomes enhance the motility of ejaculated sperm and are involved in a number...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1006/abbi.1997.9999

    authors: Carlini E,Palmerini CA,Cosmi EV,Arienti G

    更新日期:1997-07-01 00:00:00

  • RPE65, the major retinal pigment epithelium microsomal membrane protein, associates with phospholipid liposomes.

    abstract::The retinal pigment epithelium (RPE)-specific protein RPE65 is the major protein of the RPE microsomal membrane fraction. Though RPE65 lacks transmembrane domains or signal peptide, detergents are required for its maximally effective solubilization in isotonic buffers. However, in 0.75-1.0 M KCl, RPE65 is as soluble w...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1006/abbi.1997.0276

    authors: Tsilou E,Hamel CP,Yu S,Redmond TM

    更新日期:1997-10-01 00:00:00

  • Binding and internalization of atrial natriuretic factor by high-affinity receptors in A10 smooth muscle cells.

    abstract::A10 smooth muscle cells, derived from embryonic rat thoracic aorta, responded to the atrial natriuretic factor (ANF) with increased levels of cyclic GMP. These cells possess high-affinity (apparent Kd = 50 pM) plasma membrane receptors for ANF. Internalization of ANF at 37 degrees C was indicated by the following: app...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/0003-9861(86)90504-7

    authors: Napier MA,Arcuri KE,Vandlen RL

    更新日期:1986-08-01 00:00:00

  • Modulation of extracellular matrix gene expression in bovine high-density chondrocyte cultures by ascorbic acid and enzymatic resuspension.

    abstract::To define the influence of time in culture on gene expression for extracellular matrix proteins we have examined the progression of changes in gene expression for chondrocyte extracellular matrix proteins from the time the chondrocytes are initially isolated from their native cartilaginous matrix through 13 days of hi...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1006/abbi.1994.1415

    authors: Hering TM,Kollar J,Huynh TD,Varelas JB,Sandell LJ

    更新日期:1994-10-01 00:00:00

  • Methionine biosynthesis in higher plants. II. Purification and characterization of cystathionine beta-lyase from spinach chloroplasts.

    abstract::Cystathionine beta-lyase, the second enzyme of the transsulfuration pathway leading to homocysteine synthesis was purified over 16,000-fold from spinach (Spinacia oleracea L.) leaf chloroplasts (soluble fraction). Enzyme activity was followed along the purification scheme by either a colorimetric method for the determ...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1006/abbi.1995.1078

    authors: Droux M,Ravanel S,Douce R

    更新日期:1995-01-10 00:00:00

  • Antithrombin in vertebrate species: conservation of the heparin-dependent anticoagulant mechanism.

    abstract::Heparin is thought to regulate the rate of mammalian blood clotting by enhancing the activity of antithrombin, an inhibitor of coagulation enzymes. The present study establishes that this same inhibitor is present in the blood plasma of each of the terrestrial vertebrate groups including mammals, birds, reptiles, and ...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1016/0003-9861(83)90488-5

    authors: Jordan RE

    更新日期:1983-12-01 00:00:00

  • Human lactase-phlorizin hydrolase: evidence of dimerization in the endoplasmic reticulum.

    abstract::Human lactase-phlorizin hydrolase [EC 3.2.1.23-3.2.1.62] is a disaccharidase located in the microvillus membrane of small intestinal epithelial cells. The enzyme is synthesized as a precursor protein in the endoplasmic reticulum and in addition to being glycosylated is subsequently proteolytically processed to the mat...

    journal_title:Archives of biochemistry and biophysics

    pub_type: 杂志文章

    doi:10.1006/abbi.1995.9952

    authors: Grünberg J,Sterchi EE

    更新日期:1995-11-10 00:00:00