当前位置： SCI文献检索 > BIOCHEMISTRY期刊下所有文献 > Functional characterization of an NADPH dependent 2-alkyl-3-ketoalkanoic acid reductase involved in olefin biosynthesis in Stenotrophomonas maltophilia.

Functional characterization of an NADPH dependent 2-alkyl-3-ketoalkanoic acid reductase involved in olefin biosynthesis in Stenotrophomonas maltophilia.

Abstract：

:OleD is shown to play a key reductive role in the generation of alkenes (olefins) from acyl thioesters in Stenotrophomonas maltophilia. The gene coding for OleD clusters with three other genes, oleABC, and all appear to be transcribed in the same direction as an operon in various olefin producing bacteria. In this study, a series of substrates varying in chain length and stereochemistry were synthesized and used to elucidate the functional role and substrate specificity of OleD. We demonstrated that OleD, which is an NADP(H) dependent reductase, is a homodimer which catalyzes the reversible stereospecific reduction of 2-alkyl-3-ketoalkanoic acids. Maximal catalytic efficiency was observed with syn-2-decyl-3-hydroxytetradecanoic acid, with a k(cat)/K(m) 5- and 8-fold higher than for syn-2-octyl-3-hydroxydodecanoic acid and syn-2-hexyl-3-hydroxydecanoic acid, respectively. OleD activity was not observed with syn-2-butyl-3-hydroxyoctanoic acid and compounds lacking a 2-alkyl group such as 3-ketodecanoic and 3-hydroxydecanoic acids, suggesting the necessity of the 2-alkyl chain for enzyme recognition and catalysis. Using diastereomeric pairs of substrates and 4 enantiopure isomers of 2-hexyl-3-hydroxydecanoic acid of known stereochemistry, OleD was shown to have a marked stereochemical preference for the (2R,3S)-isomer. Finally, experiments involving OleA and OleD demonstrate the first 3 steps and stereochemical course in olefin formation from acyl thioesters; condensation to form a 2-alkyl-3-ketoacyl thioester, subsequent thioester hydrolysis, and ketone reduction.

journal_name

Biochemistry

journal_title

Biochemistry

authors

Bonnett SA,Papireddy K,Higgins S,del Cardayre S,Reynolds KA

doi

10.1021/bi201096w

subject

Has Abstract

pub_date

2011-11-08 00:00:00

pages

9633-40

issue

44

eissn

0006-2960

issn

1520-4995

journal_volume

50

pub_type

杂志文章

相关文献

BIOCHEMISTRY文献大全
  • Insights into Cu(I) exchange in HAH1 using quantum mechanical and molecular simulations.

    abstract：:The human antioxidant protein, HAH1, is an important participant in a Cu(I) transport chain, delivering one Cu(I) ion to the Wilson's (WND) or Menkes disease protein (MNK). Full geometry optimizations and second-derivative calculations were performed on several binding site models using the B3LYP functional to derive ...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/bi7007195

    authors： Op't Holt BT,Merz KM Jr

    更新日期：2007-07-31 00:00:00

  • Nuclear Overhauser experiments at 500 MHz on the downfield proton spectra of 5S ribonucleic acid and its complex with ribosomal protein L25.

    abstract：:The downfield (9-15 ppm) proton spectrum of Escherichia coli 5S RNA has been examined at 500 MHz by using nuclear Overhauser methods. The data confirm the existence of the terminal and procaryotic loop helices within the molecule [Fox, G. E., & Woese, C. R. (1975) Nature (London) 256, 505-506]. Very little stable, dou...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/bi00280a005

    authors： Kime MJ,Moore PB

    更新日期：1983-05-24 00:00:00

  • A protein arginine N-methyltransferase 1 (PRMT1) and 2 heteromeric interaction increases PRMT1 enzymatic activity.

    abstract：:Protein arginine N-methyltransferases (PRMTs) act in signaling pathways and gene expression by methylating arginine residues within target proteins. PRMT1 is responsible for most cellular arginine methylation activity and can work independently or in collaboration with other PRMTs. In this study, we demonstrate a dire...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/bi200644c

    authors： Pak ML,Lakowski TM,Thomas D,Vhuiyan MI,Hüsecken K,Frankel A

    更新日期：2011-09-27 00:00:00

  • Glycosylated polyproline II rods with kinks as a structural motif in plant hydroxyproline-rich glycoproteins.

    abstract：:Hydroxyproline-rich glycoproteins (HRGPs) are the major proteinaceous components of higher plant walls and the predominant components of the cell wall of the green alga Chlamydomonas reinhardtii. The GP1 protein, an HRGP of the C. reinhardtii wall, is shown to adopt a polyproline II helical configuration and to carry ...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/bi0023605

    authors： Ferris PJ,Woessner JP,Waffenschmidt S,Kilz S,Drees J,Goodenough UW

    更新日期：2001-03-06 00:00:00

  • Transmembrane topology of mammalian planar cell polarity protein Vangl1.

    abstract：:Vangl1 and Vangl2 are membrane proteins that play an important role in neurogenesis, and Vangl1/Vangl2 mutations cause neural tube defects in mice and humans. At the cellular level, Vangl proteins regulate the establishment of planar cell polarity (PCP), a process requiring membrane assembly of asymmetrically distribu...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/bi101767a

    authors： Iliescu A,Gravel M,Horth C,Apuzzo S,Gros P

    更新日期：2011-03-29 00:00:00

  • Phospholipid spin probes measure the effects of ethanol on the molecular order of liver microsomes.

    abstract：:Ethanol, in vitro, is known to perturb the molecular order of the phospholipids in biological membranes, while chronic ethanol exposure, in vivo, leads to resistance to disordering. Such changes have usually been measured by electron spin resonance, utilizing fatty acid spin probes. The use of such probes is controver...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/bi00346a012

    authors： Taraschi TF,Wu A,Rubin E

    更新日期：1985-12-03 00:00:00

  • Characterization of lens alpha-crystallin tryptophan microenvironments by room temperature phosphorescence spectroscopy.

    abstract：:Room temperature phosphorescence techniques were used to study the structural and dynamic features of the tryptophan residues in bovine alpha-crystallin. Upon excitation at 290 nm, the characteristic signature of tryptophan phosphorescence was observed with an emission maximum at 442 +/- 2 nm. The phosphorescence inte...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/bi00439a027

    authors： Berger JW,Vanderkooi JM

    更新日期：1989-06-27 00:00:00

  • Studies of individual amino acid residues of the decapeptide tyrocidine A by proton double-resonance difference spectroscopy in the correlation mode.

    abstract：:The cyclic decapeptide antibiotic tyrocidine A was studied by two relatively new methods, viz., correlation proton magnetic resonance (pmr) spectroscopy and double-resonance difference pmr spectroscopy. The correlation method of spectral accumulation provided pmr spectra of good resolution, and in addition the signal-...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/bi00673a032

    authors： Gibbons WA,Beyer CF,Dadok J,Sprecher RF,Wyssbrod HR

    更新日期：1975-01-28 00:00:00

  • Conformational Closure of the Catalytic Site of Human CD38 Induced by Calcium.

    abstract：:First identified on the surface of lymphoids as a type II transmembrane protein, CD38 has now been established to have dual functions not only as a receptor but also as a multifunctional enzyme,catalyzing the synthesis of and hydrolysis of a general calcium messenger molecule, cyclic ADP-ribose(cADPR). The receptorial...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：

    authors： Liu Q,Graeff R,Kriksunov IA,Lam CM,Lee HC,Hao Q

    更新日期：2008-12-30 00:00:00

  • Direct NMR evidence that prolidase is specific for the trans isomer of imidodipeptide substrates.

    abstract：:The in vitro hydrolysis by porcine kidney prolidase of the imidodipeptide L-alanyl-L-proline was monitored by using 1H high-resolution NMR spectroscopy. The dipeptide exists as an equilibrium mixture of isomers with cis or trans conformation about the peptide bond. The 13C and 1H NMR spectra of the dipeptide displayed...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/bi00353a016

    authors： King GF,Middlehurst CR,Kuchel PW

    更新日期：1986-03-11 00:00:00

  • Two homologues encoding human UDP-glucose:glycoprotein glucosyltransferase differ in mRNA expression and enzymatic activity.

    abstract：:UDP-glucose:glycoprotein glucosyltransferase (UGT) is a soluble protein of the endoplasmic reticulum (ER) that operates as a gatekeeper for quality control by preventing transport of improperly folded glycoproteins out of the ER. We report the isolation of two cDNAs encoding human UDP-glucose:glycoprotein glucosyltran...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/bi9916473

    authors： Arnold SM,Fessler LI,Fessler JH,Kaufman RJ

    更新日期：2000-03-07 00:00:00

  • The imine-pyridine torsion of the pyridoxal 5'-phosphate Schiff base of aspartate aminotransferase lowers its pKa in the unliganded enzyme and is crucial for the successive increase in the pKa during catalysis.

    abstract：:In aspartate aminotransferase, pyridoxal 5'-phosphate (PLP) forms a Schiff base with the epsilon-amino group of Lys258 (internal aldimine). The internal aldimine has a pKa value of 6.8. Binding of a substrate amino acid to the enzyme yields the Michaelis complex, in which PLP still forms the internal aldimine with Lys...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/bi981517e

    authors： Hayashi H,Mizuguchi H,Kagamiyama H

    更新日期：1998-10-27 00:00:00

  • Isolation and characterization of an organic solvent soluble polypeptide component from photoreceptor complexes of Rhodospirillum rubrum.

    abstract：:An organic solvent soluble polypeptide has been isolated from photoreceptor complexes and chromatophores of Rhodospirillum rubrum. After extraction of the protein from lyophilized samples with 1:1 chloroform-methanol, it was purified by column chromatography. Its isoelectric point determined by isoelectric focusing wa...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/bi00624a011

    authors： Tonn SJ,Gogel GE,Loach PA

    更新日期：1977-03-08 00:00:00

  • Effect of subunit III removal on control of cytochrome c oxidase activity by pH.

    abstract：:Studies were undertaken to assess the postulated involvement of subunit III in the proton-linked functions of cytochrome c oxidase. The effect of pH on the steady-state kinetic [corrected] parameters of subunit III containing and subunit III depleted cytochrome oxidase was determined by using beef heart and rat liver ...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/bi00417a016

    authors： Gregory LC,Ferguson-Miller S

    更新日期：1988-08-23 00:00:00

  • Interaction of diacylglycerols with phosphatidylcholine vesicles as studied by differential scanning calorimetry and fluorescence probe depolarization.

    abstract：:Mixtures of 1,2-dipalmitoylglycerol (1,2-DPG), 1,2-dioleylglycerol (1,2-DOG), 1,2-dicapryloylglycerol (1,2-DCG), 1,3-dioleylglycerol (1,3-DOG), and 1,3-dicapryloylglycerol (1,3-DCG) with dipalmitoylphosphatidylcholine (DPPC) have been studied by means of differential scanning calorimetry (DSC) and fluorescence depolar...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/bi00425a022

    authors： Ortiz A,Villalaín J,Gómez-Fernández JC

    更新日期：1988-12-13 00:00:00

  • Plant Translation Initiation Complex eIFiso4F Directs Pokeweed Antiviral Protein to Selectively Depurinate Uncapped Tobacco Etch Virus RNA.

    abstract：:Pokeweed antiviral protein (PAP) is a ribosome inactivating protein (RIP) that depurinates the sarcin/ricin loop (SRL) of rRNA, inhibiting protein synthesis. PAP depurinates viral RNA, and in doing so, lowers the infectivity of many plant viruses. The mechanism by which PAP accesses uncapped viral RNA is not known, im...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/acs.biochem.7b00598

    authors： Domashevskiy AV,Williams S,Kluge C,Cheng SY

    更新日期：2017-11-14 00:00:00

  • Further characterization of the subunits of the receptor with high affinity for immunoglobulin E.

    abstract：:The alpha, beta, and gamma subunits of the receptor with high affinity for immunoglobulin E were isolated and their compositions assessed by direct amino acid analysis and by incorporation of radioactive precursors. The compositions show no unusual features other than a rather high content of tryptophan in the alpha c...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/bi00383a024

    authors： Alcaraz G,Kinet JP,Liu TY,Metzger H

    更新日期：1987-05-05 00:00:00

  • A convenient gHMQC-based NMR assay for investigating ammonia channeling in glutamine-dependent amidotransferases: studies of Escherichia coli asparagine synthetase B.

    abstract：:X-ray crystal structures of glutamine-dependent amidotransferases in their "active" conformation have revealed the existence of multiple active sites linked by solvent inaccessible intramolecular channels, giving rise to the widely accepted view that ammonia released in a glutaminase site is channeled efficiently into...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/bi700145t

    authors： Li KK,Beeson WT 4th,Ghiviriga I,Richards NG

    更新日期：2007-04-24 00:00:00

  • Regulation of plasminogen activation by components of the extracellular matrix.

    abstract：:The kinetics of activation of Glu-plasminogen (Glu-Pg) and Lys77-Pg by two-chain recombinant tissue plasminogen activator (t-PA) were determined in the presence of isolated protein components of the extracellular matrix (ECM) and compared to activation in the presence of fibrinogen and fibrinogen fragments and in the ...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/bi00472a029

    authors： Stack S,Gonzalez-Gronow M,Pizzo SV

    更新日期：1990-05-22 00:00:00

  • Induction of stable protein-deoxyribonucleic acid adducts in Chinese hamster cell chromatin by ultraviolet light.

    abstract：:Ultraviolet (uv)-light-mediated formation of protein-DNA adducts in Chinese hamster cell chromatin was investigated in an attempt to compare chromatin alterations induced in vitro with those observed in vivo. Three independent methods of analysis indicated stable protein-DNA associations: (1) a membrane filter assay w...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/bi00653a019

    authors： Strniste GF,Rall SC

    更新日期：1976-04-20 00:00:00

  • Kinetic and structural analysis of enzyme sliding on a substrate: multiple attack in beta-amylase.

    abstract：:Beta-amylase (EC 3.2.1.2) is starch-hydrolyzing exo-type enzyme that can catalyze the successive liberation of beta-maltose from the nonreducing ends of alpha-1,4-linked glucopyranosyl polymers. There is a well-known phenomenon called multiple or repetitive attack where the enzyme releases several maltose molecules in...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/bi061605w

    authors： Ishikawa K,Nakatani H,Katsuya Y,Fukazawa C

    更新日期：2007-01-23 00:00:00

  • Streptokinase binds preferentially to the extended conformation of plasminogen through lysine binding site and catalytic domain interactions.

    abstract：:Binding of streptokinase (SK) to plasminogen (Pg) activates the zymogen conformationally and initiates its conversion into the fibrinolytic proteinase, plasmin (Pm). Equilibrium binding studies of SK interactions with a homologous series of catalytic site-labeled fluorescent Pg and Pm analogues were performed to resol...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/bi000594i

    authors： Boxrud PD,Bock PE

    更新日期：2000-11-14 00:00:00

  • Lysine 2,3-aminomutase: rapid mix-freeze-quench electron paramagnetic resonance studies establishing the kinetic competence of a substrate-based radical intermediate.

    abstract：:Lysine 2,3-aminomutase from Clostridia catalyzes the interconversion of L-lysine and L-beta-lysine. The enzyme contains iron-sulfur clusters and is activated by pyridoxal 5'-phosphate and S-adenosylmethionine, all of which participate in catalysis. Current spectroscopic evidence implicates two substrate-based organic ...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/bi960850k

    authors： Chang CH,Ballinger MD,Reed GH,Frey PA

    更新日期：1996-08-27 00:00:00

  • Halogen Bonding: A Powerful Tool for Modulation of Peptide Conformation.

    abstract：:Halogen bonding is a weak chemical force that has so far mostly found applications in crystal engineering. Despite its potential for use in drug discovery, as a new molecular tool in the direction of molecular recognition events, it has rarely been assessed in biopolymers. Motivated by this fact, we have developed a p...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/acs.biochem.7b00429

    authors： Danelius E,Andersson H,Jarvoll P,Lood K,Gräfenstein J,Erdélyi M

    更新日期：2017-06-27 00:00:00

  • Human CD4 Metastability Is a Function of the Allosteric Disulfide Bond in Domain 2.

    abstract：:CD4 is expressed on the surface of specific leukocytes where it plays a key role in the activation of immunostimulatory T-cells and acts as a primary receptor for HIV-1 entry. CD4 has four ecto-domains (D1-D4) of which D1, D2, and D4 contain disulfide bonds. Although disulfide bonds commonly serve structural or cataly...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/acs.biochem.6b00154

    authors： Owen GR,Channell JA,Forsyth VT,Haertlein M,Mitchell EP,Capovilla A,Papathanasopoulos M,Cerutti NM

    更新日期：2016-04-19 00:00:00

  • Structures of Pseudomonas aeruginosa LpxA Reveal the Basis for Its Substrate Selectivity.

    abstract：:In Gram-negative bacteria, the first step of lipid A biosynthesis is catalyzed by UDP-N-acetylglucosamine acyltransferase (LpxA) through the transfer of a R-3-hydroxyacyl chain from the acyl carrier protein (ACP) to the 3-hydroxyl group of UDP-GlcNAc. Previous studies suggest that LpxA is a critical determinant of the...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/acs.biochem.5b00720

    authors： Smith EW,Zhang X,Behzadi C,Andrews LD,Cohen F,Chen Y

    更新日期：2015-09-29 00:00:00

  • Structure-activity analysis of the effects of lysophosphatidic acid on platelet aggregation.

    abstract：:Lysophosphatidic acid (1-acyl-sn-glycero-3-phosphate or LPA) is a phospholipid mediator displaying numerous and widespread biological activities and thought to act via G-protein-coupled receptors. Here we have studied the effects on human platelets of a number of LPA analogues, including two enantiomers of both N-palm...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/bi9816756

    authors： Gueguen G,Gaigé B,Grévy JM,Rogalle P,Bellan J,Wilson M,Klaébé A,Pont F,Simon MF,Chap H

    更新日期：1999-06-29 00:00:00

  • Acquisition of an insertion peptide for efficient aminoacylation by a halophile tRNA synthetase.

    abstract：:Enzymes of halophilic organisms contain unusual peptide motifs that are absent from their mesophilic counterparts. The functions of these halophile-specific peptides are largely unknown. Here we have identified an unusual peptide that is unique to several halophile archaeal cysteinyl-tRNA synthetases (CysRS), which ca...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/bi0521386

    authors： Evilia C,Hou YM

    更新日期：2006-06-06 00:00:00

  • Quantitative measurement of Ca(2+)-dependent calmodulin-target binding by Fura-2 and CFP and YFP FRET imaging in living cells.

    abstract：:Calcium dynamics and its linked molecular interactions cause a variety of biological responses; thus, exploiting techniques for detecting both concurrently is essential. Here we describe a method for measuring the cytosolic Ca(2+) concentration ([Ca(2+)](i)) and protein-protein interactions within the same cell, using...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/bi200287x

    authors： Mori MX,Imai Y,Itsuki K,Inoue R

    更新日期：2011-05-31 00:00:00

  • Thermal behavior of synthetic sphingomyelin-cholesterol dispersions.

    abstract：:The thermotropic behavior of aqueous dispersions of palmitoylsphingomyelin-cholesterol and lignoceryl-sphingomyelin-cholesterol mixtures has been examined by high-sensitivity differential scanning calorimetry. When less than 25 mol % cholesterol is mixed with either sphingomyelin, the calorimetric endotherm is compose...

    journal_title：Biochemistry

    pub_type： 杂志文章

    doi：10.1021/bi00577a042

    authors： Estep TN,Mountcastle DB,Barenholz Y,Biltonen RL,Thompson TE

    更新日期：1979-05-15 00:00:00