Characterization of the lysyl adducts of prostaglandin H-synthases that are derived from oxygenation of arachidonic acid.

Abstract:

:These investigations characterize the covalent binding of reactive products of prostaglandin H-synthases (PGHSs) to the enzyme and to other molecules. The intermediate product of oxygenation of arachidonic acid by the PGHSs, prostaglandin (PG) H2, undergoes rearrangement to the highly reactive gamma-keto aldehydes, levuglandin (LG) E2 and D2. We previously have demonstrated that LGE2 reacts with the epsilon-amine of lysine to form both the lysyl-levuglandin Shiff base and the pyrrole-derived lysyl-levuglandin lactam adducts. We now demonstrate that these lysyl-levuglandin adducts are formed on the PGHSs following the oxygenation of arachidonic acid; after reduction of the putative Schiff base, proteolytic digestion of the enzyme, and isolation of the adducted amino acid residues, these adducts were identified by liquid chromatography-tandem mass spectrometry. The reactivity of the LGs is reflected by the finding that virtually all of the LG predicted to be formed from PGH2 can be accounted for as adducts of the PGH-synthase and that oxygenation of arachidonic acid by PGH-synthases also leads to the formation of adducts of other proteins present in the reaction solution. The reactivity of the PGH-synthase adducts themselves is demonstrated by the formation of intermolecular cross-links.

journal_name

Biochemistry

journal_title

Biochemistry

authors

Boutaud O,Brame CJ,Chaurand P,Li J,Rowlinson SW,Crews BC,Ji C,Marnett LJ,Caprioli RM,Roberts LJ 2nd,Oates JA

doi

10.1021/bi002629k

subject

Has Abstract

pub_date

2001-06-12 00:00:00

pages

6948-55

issue

23

eissn

0006-2960

issn

1520-4995

pii

bi002629k

journal_volume

40

pub_type

杂志文章
  • Urea Mimics Nucleobases by Preserving the Helical Integrity of B-DNA Duplexes via Hydrogen Bonding and Stacking Interactions.

    abstract::Urea lesions are formed in DNA because of free radical damage of the thymine base, and their occurrence in DNA blocks DNA polymerases, which has deleterious consequences. Recently, it has been shown that urea is capable of forming hydrogen bonding and stacking interactions with nucleobases, which are responsible for t...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/acs.biochem.6b00309

    authors: Suresh G,Padhi S,Patil I,Priyakumar UD

    更新日期:2016-10-11 00:00:00

  • Phenotypic regulation of the sphingosine 1-phosphate receptor miles apart by G protein-coupled receptor kinase 2.

    abstract::The evolutionarily conserved DRY motif at the end of the third helix of rhodopsin-like, class-A G protein-coupled receptors (GPCRs) is a major regulator of receptor stability, signaling activity, and β-arrestin-mediated internalization. Substitution of the DRY arginine with histidine in the human vasopressin receptor ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi501061h

    authors: Burczyk M,Burkhalter MD,Blätte T,Matysik S,Caron MG,Barak LS,Philipp M

    更新日期:2015-01-27 00:00:00

  • Rate and extent of poly(ethylene glycol)-induced large vesicle fusion monitored by bilayer and internal contents mixing.

    abstract::Poly(ethylene glycol) (PEG) of average molecular weight 8000 was used to mediate the fusion of large unilamellar vesicles composed of dipalmitoylphosphatidylcholine. Fusion was monitored by fluorescence assays of lipid mixing and aqueous contents mixing. The extent of lipid mixing, as monitored by DPHpPC fluorescence ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00369a053

    authors: Parente RA,Lentz BR

    更新日期:1986-10-21 00:00:00

  • Insight into the mechanism of serpin-proteinase inhibition from 2D [1H-15N] NMR studies of the 69 kDa alpha 1-proteinase inhibitor Pittsburgh-trypsin covalent complex.

    abstract::We have used [(1)H-(15)N]-HSQC NMR to investigate the structural changes that occur in both serpin and proteinase in forming the kinetically trapped covalent protein-protein complex that is the basis for serpin inhibition of serine proteinases. By alternately using (15)N-alanine specifically-labeled alpha(1)-proteinas...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi010100x

    authors: Peterson FC,Gettins PG

    更新日期:2001-05-29 00:00:00

  • Spin-label electron paramagnetic resonance and differential scanning calorimetry studies of the interaction between mitochondrial cytochrome c oxidase and adenosine triphosphate synthase complex.

    abstract::The interaction between cytochrome c oxidase complex and adenosine triphosphate synthase (F1F0) complex in the purified, dispersed state and embedded in phospholipid vesicles was studied by differential scanning calorimetry and by spin-label electron paramagnetic resonance. The detergent-dispersed cytochrome oxidase a...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00127a036

    authors: Qiu ZH,Yu L,Yu CA

    更新日期:1992-03-31 00:00:00

  • The swapping of terminal arms in ribonucleases: comparison of the solution structure of monomeric bovine seminal and pancreatic ribonucleases.

    abstract::Bovine seminal ribonuclease (BS-RNase), the only dimeric protein among the pancreatic-like ribonucleases, is endowed with special structural features and with biological functions beyond enzymatic activity. In solution, the protein exists as an equilibrium mixture of two forms, with or without exchange (or swapping) o...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi0342517

    authors: Avitabile F,Alfano C,Spadaccini R,Crescenzi O,D'Ursi AM,D'Alessio G,Tancredi T,Picone D

    更新日期:2003-07-29 00:00:00

  • Regulation of the expression of the β-lactam antibiotic-resistance determinants in methicillin-resistant Staphylococcus aureus (MRSA).

    abstract::β-Lactam antibiotics have faced obsolescence with the emergence of methicillin-resistant Staphylococcus aureus (MRSA). A complex set of events ensues upon exposure of MRSA to these antibiotics, which culminates in proteolysis of BlaI or MecI, two gene repressors, and results in the induction of resistance. We report s...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi500074w

    authors: Blázquez B,Llarrull LI,Luque-Ortega JR,Alfonso C,Boggess B,Mobashery S

    更新日期:2014-03-18 00:00:00

  • Crystal structure of rabbit cytosolic serine hydroxymethyltransferase at 2.8 A resolution: mechanistic implications.

    abstract::Serine hydroxymethyltransferase (SHMT) catalyzes the reversible cleavage of serine to form glycine and single carbon groups that are essential for many biosynthetic pathways. SHMT requires both pyridoxal phosphate (PLP) and tetrahydropteroylpolyglutamate (H4PteGlun) as cofactors, the latter as a carrier of the single ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi9904151

    authors: Scarsdale JN,Kazanina G,Radaev S,Schirch V,Wright HT

    更新日期:1999-06-29 00:00:00

  • Revisiting the Val/Ile Mutation in Mammalian and Bacterial Nitric Oxide Synthases: A Spectroscopic and Kinetic Study.

    abstract::Nitric oxide is produced in mammals by the nitric oxide synthase (NOS) isoforms at a catalytic site comprising a heme associated with a biopterin cofactor. Through genome sequencing, proteins that are highly homologous to the oxygenase domain of NOSs have been identified, in particular in bacteria. The active site is ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/acs.biochem.6b01018

    authors: Weisslocker-Schaetzel M,Lembrouk M,Santolini J,Dorlet P

    更新日期:2017-02-07 00:00:00

  • Association of membrane and cytoplasmic proteins with the cytoskeleton in blood platelets.

    abstract::The association of membrane and cytoplasmic proteins with the cytoskeleton of resting and activated platelets was studied. Glycoproteins were identified by labeling with 125I-labeled lectins (concanavalin A, wheat germ agglutinin, and Lens culinaris). Polypeptides, which are embedded in the lipid bilayer, have been id...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00537a002

    authors: Rotman A,Heldman J,Linder S

    更新日期:1982-04-13 00:00:00

  • Brevin and vitamin D binding protein: comparison of the effects of two serum proteins on actin assembly and disassembly.

    abstract::Actin depolymerizing activity in serum can be attributed to the two proteins brevin and vitamin D binding protein (DBP). To investigate their mechanisms of action, we used a number of techniques, including procedures involving the fluorescent pyrene-labeled actin probe, to compare the interaction of the two proteins w...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00308a030

    authors: Lees A,Haddad JG,Lin S

    更新日期:1984-06-19 00:00:00

  • Equilibrium binding of myristoyllysophosphatidylcholine to bovine myelin basic protein: an example of ligand-mediated acceptor association.

    abstract::The interaction of myristoyllysophosphatidylcholine with bovine myelin basic protein at pH 7.4 and 4.5, I = 0.48, has been investigated by a recycling partition equilibrium technique with Bio-Gel P-2 as the gel phase. Important points to emerge from this direct binding study are that it is a monomeric (not micellar) a...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00378a002

    authors: Gow A,Winzor DJ,Smith R

    更新日期:1987-02-24 00:00:00

  • Specific binding of human dihydrofolate reductase protein to dihydrofolate reductase messenger RNA in vitro.

    abstract::Dihydrofolate reductase (DHFR) is a critical enzyme in de novo purine and thymidylate biosynthesis. An RNA gel mobility shift assay was used to demonstrate a specific interaction between human recombinant DHFR protein and its corresponding DHFR mRNA. Incubation of DHFR protein with either its substrates, dihydrofolate...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00069a009

    authors: Chu E,Takimoto CH,Voeller D,Grem JL,Allegra CJ

    更新日期:1993-05-11 00:00:00

  • Thermodynamic characterization of ligand-induced conformational changes in UDP-N-acetylglucosamine enolpyruvyl transferase.

    abstract::The binding of UDP-N-acetylglucosamine (UDPNAG) to the enzyme UDP-N-acetylglucosamine enolpyruvyl transferase (MurA) was studied in the absence and presence of the antibiotic fosfomycin by isothermal titration calorimetry. Fosfomycin binds covalently to MurA in the presence of UDPNAG and also in its absence as demonst...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi0107041

    authors: Samland AK,Jelesarov I,Kuhn R,Amrhein N,Macheroux P

    更新日期:2001-08-21 00:00:00

  • Determinants of high-affinity DNA binding by the glucocorticoid receptor: evaluation of receptor domains outside the DNA-binding domain.

    abstract::In this study, we have investigated the influence of regions outside the DNA-binding domain of the human glucocorticoid receptor on high-affinity DNA binding. We find that the DNA-binding domain shows a 10-fold lower affinity for a palindromic DNA-binding site than the intact receptor. The N-terminal part of the recep...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00152a047

    authors: Dahlman-Wright K,Wright AP,Gustafsson JA

    更新日期:1992-09-22 00:00:00

  • Kinetic and Bioinformatic Characterization of d-2-Hydroxyglutarate Dehydrogenase from Pseudomonas aeruginosa PAO1.

    abstract::d-2-Hydroxyglutarate dehydrogenase from Pseudomonas aeruginosa PAO1 (PaD2HGDH) catalyzes the oxidation of d-2-hydroxyglutarate to 2-ketoglutarate, which is a necessary step in the serine biosynthetic pathway. The dependence of P. aeruginosa on PaD2HGDH makes the enzyme a potential therapeutic target against P. aerugin...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/acs.biochem.0c00832

    authors: Quaye JA,Gadda G

    更新日期:2020-12-29 00:00:00

  • Alzheimer's Abeta peptides containing an isostructural backbone mutation afford distinct aggregate morphologies but analogous cytotoxicity. Evidence for a common low-abundance toxic structure(s)?

    abstract::Amyloid beta (Abeta) peptide amyloidogenesis, involving the formation of numerous distinct quaternary structures, appears to cause Alzheimer's disease. However, the precise identification of the toxic structure(s) and the neurotoxicity mechanism(s) remains elusive. Mutating the Abeta 1-40 Phe19-Phe20 backbone amide bo...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi701757v

    authors: Bieschke J,Siegel SJ,Fu Y,Kelly JW

    更新日期:2008-01-08 00:00:00

  • Intramolecular dephosphorylation of ERK by MKP3.

    abstract::The dual specificity mitogen-activated protein kinase phosphatase MKP3 downregulates mitogenic signaling through dephosphorylation of extracellular signal-regulated kinase (ERK). Like other MKPs, MKP3 consists of a noncatalytic N-terminal domain and a catalytic C-terminal domain. ERK binding to the N-terminal noncatal...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi035346b

    authors: Kim Y,Rice AE,Denu JM

    更新日期:2003-12-30 00:00:00

  • The malonyl/acetyltransferase and beta-ketoacyl synthase domains of the animal fatty acid synthase can cooperate with the acyl carrier protein domain of either subunit.

    abstract::The active form of the animal fatty acid synthase (FAS) is a dimer of identical multifunctional polypeptides, each containing seven discrete functional domains, that cooperate to form two centers for palmitate synthesis. To assess the importance of domain cooperation across the subunit interface in the reaction mechan...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi971886v

    authors: Joshi AK,Witkowski A,Smith S

    更新日期:1998-02-24 00:00:00

  • Pyruvate dehydrogenase kinase isoform 2 activity limited and further inhibited by slowing down the rate of dissociation of ADP.

    abstract::Pyruvate dehydrogenase kinase 2 (PDK2) activity is enhanced by the dihydrolipoyl acetyltransferase core (E2 60mer) that binds PDK2 and a large number of its pyruvate dehydrogenase (E1) substrate. With E2-activated PDK2, K(+) at approximately 90 mM and Cl(-) at approximately 60 mM decreased the K(m) of PDK2 for ATP and...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi049488x

    authors: Bao H,Kasten SA,Yan X,Roche TE

    更新日期:2004-10-26 00:00:00

  • Synthesis and characterization of a new fluorogenic active-site titrant of serine proteases.

    abstract::The molecule 3',6'-bis(4-guanidinobenzoyloxy)-5-[N'-(4-carboxyphenyl)thioureido[spirop]isobenzofuran-1-(3H),9'-[9H]xanthen]-3-one, abbreviated FDE, was designed and synthesized as a fluorogenic active-site titrant for serine proteases. It is an analogue of p-nitrophenyl p-guanidino-benzoate (NPGB) in which a fluoresce...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00518a010

    authors: Livingston DC,Brocklehurst JR,Cannon JF,Leytus SP,Wehrly JA,Peltz SW,Peltz GA,Mangel WF

    更新日期:1981-07-21 00:00:00

  • Identification of electrostatic interactions that determine the phosphorylation site specificity of the cAMP-dependent protein kinase.

    abstract::"Charged-to alanine" scanning mutagenesis of the catalytic subunit of the Saccharomyces cerevisiae cAMP-dependent protein kinase (C1) identified three glutamate residues, E171, E214, and E274, that are involved in the recognition of a peptide substrate, kemptide (Leu1Arg2Arg3Ala4Ser5Leu6Gly7). These glutamate residues...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00236a001

    authors: Gibbs CS,Zoller MJ

    更新日期:1991-06-04 00:00:00

  • Functional dissection of the dimerization and enzymatic activities of Escherichia coli nitrogen regulator II and their regulation by the PII protein.

    abstract::The dimeric two-component system transmitter protein NRII (NtrB) of Escherichia coli, product of glnL (ntrB), controls transcription of nitrogen-regulated genes by catalyzing the phosphorylation and dephosphorylation of the transcription factor NRI (NtrC). Previous studies showed that the PII signal transduction prote...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi000794u

    authors: Jiang P,Atkinson MR,Srisawat C,Sun Q,Ninfa AJ

    更新日期:2000-11-07 00:00:00

  • A general framework for development and data analysis of competitive high-throughput screens for small-molecule inhibitors of protein-protein interactions by fluorescence polarization.

    abstract::Equilibrium binding experiments are widely used for the accurate characterization of binding and competitive binding behavior in biological systems. Modern high-throughput discovery efforts in chemical biology rely heavily upon this principle. Here, we derive exact analytical expressions for general competitive bindin...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi048233g

    authors: Roehrl MH,Wang JY,Wagner G

    更新日期:2004-12-28 00:00:00

  • Rat organic anion transporting protein 1A1 (Oatp1a1): purification and phosphopeptide assignment.

    abstract::Rat organic anion transporting protein 1a1 (oatp1a1), a hepatocyte basolateral plasma membrane protein, mediates transport of various amphipathic compounds. Our previous studies indicated that serine phosphorylation of a single tryptic peptide inhibits its transport activity without changing its cell surface content. ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi052437v

    authors: Xiao Y,Nieves E,Angeletti RH,Orr GA,Wolkoff AW

    更新日期:2006-03-14 00:00:00

  • Conformational flexibility of PEP mutase.

    abstract::Previous work has indicated that PEP mutase catalyzes the rearrangement of phosphoenolpyruvate to phosphonopyruvate by a dissociative mechanism. The crystal structure of the mutase with Mg(II) and sulfopyruvate (a phosphonopyruvate analogue) bound showed that the substrate is anchored to the active site by the Mg(II),...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi036255h

    authors: Liu S,Lu Z,Han Y,Jia Y,Howard A,Dunaway-Mariano D,Herzberg O

    更新日期:2004-04-20 00:00:00

  • Calmodulin binding to rat adipocyte plasma membrane: characterization and photoaffinity cross-linking of calmodulin to binding proteins.

    abstract::[125I]Calmodulin binding to isolated rat adipocyte plasma membranes has been characterized, and the calmodulin binding proteins associated with the membrane have been identified by use of the photoaffinity cross-linker N-hydroxysuccinimidyl 4-azidobenzoate. Total binding of [125I]calmodulin to plasma membranes was ass...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00264a029

    authors: Goewert RR,Landt M,McDonald JM

    更新日期:1982-10-12 00:00:00

  • Solution structure of the paramagnetic complex of the N-terminal domain of calmodulin with two Ce3+ ions by 1H NMR.

    abstract::The solution structure of the dicerium(III) complex of the N-terminal domain of calmodulin (Ce2-TR1C hereafter) has been solved employing paramagnetic T1 relaxation enhancements and pseudocontact shifts introduced by the Ce3+ ions, together with conventional NOE constraints. The use of pseudocontact shift constraints ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi971022+

    authors: Bentrop D,Bertini I,Cremonini MA,Forsén S,Luchinat C,Malmendal A

    更新日期:1997-09-30 00:00:00

  • Domain organization and functional analysis of type IIS restriction endonuclease Eco31I.

    abstract::Type IIS restriction endonuclease Eco31I harbors a single HNH active site and cleaves both DNA strands close to its recognition sequence, 5'-GGTCTC(1/5). A two-domain organization of Eco31I was determined by limited proteolysis. Analysis of proteolytic fragments revealed that the N-terminal domain of Eco31I is respons...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi800660u

    authors: Jakubauskas A,Sasnauskas G,Giedriene J,Janulaitis A

    更新日期:2008-08-19 00:00:00

  • The nickel site of Bacillus pasteurii UreE, a urease metallo-chaperone, as revealed by metal-binding studies and X-ray absorption spectroscopy.

    abstract::UreE is a homodimeric metallo-chaperone that assists the insertion of Ni(2+) ions in the active site of urease. The crystal structures of UreE from Bacillus pasteurii and Klebsiella aerogenes have been determined, but the details of the nickel-binding site were not elucidated due to solid-state effects that caused dis...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi0601003

    authors: Stola M,Musiani F,Mangani S,Turano P,Safarov N,Zambelli B,Ciurli S

    更新日期:2006-05-23 00:00:00