Preparation and Application of 13C-Labeled myo-Inositol to Identify New Catabolic Products in Inositol Metabolism in Lactobacillus casei.

Abstract:

:myo-Inositol (mI) is widely distributed in all domains of life and is important for several cellular functions, including bacterial survival. The enzymes responsible for the bacterial catabolism of mI, encoded in the iol operon, can vary from one organism to another, and these pathways have yet to be fully characterized. We previously identified a new scyllo-inositol dehydrogenase (sIDH) in the iol operon of Lactobacillus casei that can oxidize mI in addition to the natural substrate, scyllo-inositol, but the product of mI oxidation was not determined. Here we report the identification of these metabolites by monitoring the reaction with 13C nuclear magnetic resonance. We prepared all six singly 13C-labeled mI isotopomers through a biocatalytic approach and used these labeled inositols as substrates for sIDH. The use of all six singly labeled mI isotopomers allowed for metabolite characterization without isolation steps. sIDH oxidation of mI produces 1l-5-myo-inosose preferentially, but also two minor products, 1d-chiro-inosose and 1l-chiro-inosose. Together with previous crystal structure data for sIDH, we were able to rationalize the observed oxidation preference. Our relatively simple procedure for the preparation of isotopically labeled mI standards can have broad applications for the study of mI biotransformations.

journal_name

Biochemistry

journal_title

Biochemistry

authors

Ramos-Figueroa JS,Aamudalapalli HB,Jagdhane RC,Smith J,Palmer DRJ

doi

10.1021/acs.biochem.0c00539

subject

Has Abstract

pub_date

2020-08-18 00:00:00

pages

2974-2985

issue

32

eissn

0006-2960

issn

1520-4995

journal_volume

59

pub_type

杂志文章
  • Tritium isotope effects in adenosylcobalamin-dependent methylmalonyl-CoA mutase.

    abstract::Methylmalonyl-CoA mutase from Propionibacterium shermanii is an adenosylcobalamin-dependent enzyme which catalyzes the reversible isomerization of methylmalonyl-CoA and succinyl-CoA. The rate of tritium loss from 5'-[3H]adenosylcobalamin during the enzymic reaction and the relative rates of tritium appearance in subst...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi961250o

    authors: Meier TW,Thomä NH,Leadlay PF

    更新日期:1996-09-10 00:00:00

  • Mechanistic characterization of the bifunctional aminoglycoside-modifying enzyme AAC(3)-Ib/AAC(6')-Ib' from Pseudomonas aeruginosa.

    abstract::A recently discovered bifunctional antibiotic-resistance enzyme named AAC(3)-Ib/AAC(6')-Ib', from Pseudomonas aeruginosa, catalyzes acetylation of aminoglycoside antibiotics. Since both domains are acetyltransferases, each was cloned and purified for mechanistic studies. The AAC(3)-Ib domain appears to be highly speci...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi700111z

    authors: Kim C,Villegas-Estrada A,Hesek D,Mobashery S

    更新日期:2007-05-01 00:00:00

  • Structural homology discloses a bifunctional structural motif at the N-termini of G alpha proteins.

    abstract::In a family of proteins, often the three-dimensional structure has been experimentally determined only for one member or a few members of the family. Homology modeling can be used to model the structures of all other members of the family and thus allow comparison of these structures. This approach was applied to hete...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi026729x

    authors: Kosloff M,Elia N,Selinger Z

    更新日期:2002-12-10 00:00:00

  • The subcellular distribution of adenylate and guanylate cyclases in murine lymphoid cells.

    abstract::Membrane vesicles can be prepared from murine lymphoid cells by nitrogen cavitation and fractionated by sedimentation through nonlinear sucrose density gradients. Two subpopulations of membrane vesicles, PMI and PMII, can be distinguished on the basis of sedimentation rate. The subcellular distribution of adenylate an...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00652a026

    authors: Watson J,Nilsen-Hamilton M,Hamilton RT

    更新日期:1976-04-06 00:00:00

  • Molecular properties of p-(dimethylamino)benzaldehyde bound to liver alcohol dehydrogenase: a Raman spectroscopic study.

    abstract::We have studied the binding nature of an aromatic aldehyde to the catalytic site of liver alcohol dehydrogenase from horse (LADH) using preresonance Raman spectroscopy. The compound p-(dimethylamino)benzaldehyde (DABA) is converted to the corresponding alcohol in the presence of nicotinamide adenine dinucleotide (NADH...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00410a023

    authors: Callender R,Chen D,Lugtenburg J,Martin C,Rhee KW,Sloan D,Vandersteen R,Yue KT

    更新日期:1988-05-17 00:00:00

  • Crystal structure of eta-crystallin: adaptation of a class 1 aldehyde dehydrogenase for a new role in the eye lens.

    abstract::Eta-crystallin is a retinal dehydrogenase that has acquired a role as a structural protein in the eye lens of elephant shrews, members of an ancient order of mammals. While it retains some activity toward retinal, which is oxidized to retinoic acid, the protein has acquired a number of specific sequence changes that h...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi027367w

    authors: Bateman OA,Purkiss AG,van Montfort R,Slingsby C,Graham C,Wistow G

    更新日期:2003-04-22 00:00:00

  • Amyloid fibrillation of human Apaf-1 CARD.

    abstract::The idea of establishing the amyloid-like fibrillation tendency of pro- and antisurvival proteins of human apoptotic pathways is relevant for delineating the conditions that lead to aberrant differentiation, development, and tissue homeostasis. As the first step in this direction, we report here that the caspase recru...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi900626u

    authors: Rao PN,Reddy KS,Bhuyan AK

    更新日期:2009-08-18 00:00:00

  • Oligonucleotide-directed nucleic acid scission by micrococcal nuclease.

    abstract::"Sequence-dictated" scission of DNA can be achieved by tethering a fusion protein composed of glutathione S-transferase and attenuated micrococcal nuclease (MN) to a targeting oligonucleotide using Cibacron blue (CB) F3G-A. Deoxyoligonucleotides derivatized with this dye bind to the fusion protein in gel mobility shif...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00201a006

    authors: Landgraf R,Chen CH,Sigman DS

    更新日期:1994-09-06 00:00:00

  • The family 1 beta-glucosidases from Pyrococcus furiosus and Agrobacterium faecalis share a common catalytic mechanism.

    abstract::Comparisons of catalytic mechanisms have not previously been performed for homologous enzymes from hyperthermophilic and mesophilic sources. Here, the beta-glucosidase from the hyperthermophilic archaeon Pyrococcus furiosus was recombinantly produced in Escherichia coli and shown to have biophyscial and biochemical pr...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi9814944

    authors: Bauer MW,Kelly RM

    更新日期:1998-12-08 00:00:00

  • Identification of contact sites between ankyrin and band 3 in the human erythrocyte membrane.

    abstract::The red cell membrane is stabilized by a spectrin/actin-based cortical cytoskeleton connected to the phospholipid bilayer via multiple protein bridges. By virtue of its interaction with ankyrin and adducin, the anion transporter, band 3 (AE1), contributes prominently to these bridges. In a previous study, we demonstra...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi300693k

    authors: Grey JL,Kodippili GC,Simon K,Low PS

    更新日期:2012-08-28 00:00:00

  • Crystal structure of the potent natural product inhibitor balanol in complex with the catalytic subunit of cAMP-dependent protein kinase.

    abstract::Endogenous protein kinase inhibitors are essential for a wide range of physiological functions. These endogenous inhibitors may mimic peptide substrates as in the case of the heat-stable protein kinase inhibitor (PKI), or they may mimic nucleotide triphosphates. Natural product inhibitors, endogenous to the unique org...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi9820659

    authors: Narayana N,Diller TC,Koide K,Bunnage ME,Nicolaou KC,Brunton LL,Xuong NH,Ten Eyck LF,Taylor SS

    更新日期:1999-02-23 00:00:00

  • Irreversible inhibition of serine proteases by peptide derivatives of (alpha-aminoalkyl)phosphonate diphenyl esters.

    abstract::Peptidyl derivatives of diphenyl (alpha-aminoalkyl)phosphonates have been synthesized and are effective and specific inhibitors of serine proteases at low concentrations. Z-PheP(OPh)2 irreversibly reacts with chymotrypsin (kobsd/[I] = 1200 M-1 s-1) and does not react with two elastases. The best inhibitor for most chy...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00216a026

    authors: Oleksyszyn J,Powers JC

    更新日期:1991-01-15 00:00:00

  • Expression of cytochrome P-450 and albumin genes in rat liver: effect of xenobiotics.

    abstract::Thioacetamide, a hepatocarcinogen and an inhibitor of heme synthesis, blocks the phenobarbitone-mediated increase in the transcription of cytochrome P-450b+e messenger RNA in rat liver. This property is also shared by CoCl2 and 3-amino-1,2,4-triazole, two other inhibitors of heme synthesis. Thus, it appears feasible t...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00364a009

    authors: Satyabhama S,Seelan RS,Padmanaban G

    更新日期:1986-08-12 00:00:00

  • The dimerization stability of the HLH-LZ transcription protein family is modulated by the leucine zippers: a CD and NMR study of TFEB and c-Myc.

    abstract::In the HLH-LZ protein family, the helix-loop-helix DNA-binding dimerization domain is followed in the sequence by a leucine zipper motif. The precise function of this second dimerization domain is still unclear, since the HLH motif of a subset of this family has been shown to be necessary and sufficient for dimerizati...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00203a027

    authors: Muhle-Goll C,Gibson T,Schuck P,Schubert D,Nalis D,Nilges M,Pastore A

    更新日期:1994-09-20 00:00:00

  • Structure of a specialized acyl carrier protein essential for lipid A biosynthesis with very long-chain fatty acids in open and closed conformations.

    abstract::The solution nuclear magnetic resonance (NMR) structures and backbone (15)N dynamics of the specialized acyl carrier protein (ACP), RpAcpXL, from Rhodopseudomonas palustris, in both the apo form and holo form modified by covalent attachment of 4'-phosphopantetheine at S37, are virtually identical, monomeric, and corre...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi300546b

    authors: Ramelot TA,Rossi P,Forouhar F,Lee HW,Yang Y,Ni S,Unser S,Lew S,Seetharaman J,Xiao R,Acton TB,Everett JK,Prestegard JH,Hunt JF,Montelione GT,Kennedy MA

    更新日期:2012-09-18 00:00:00

  • Structure of the cytoplasmic loop between putative helices II and III of the mannitol permease of Escherichia coli: a tryptophan and 5-fluorotryptophan spectroscopy study.

    abstract::In this work, four single tryptophan (Trp) mutants of the dimeric mannitol transporter of Escherichia coli, EII(mtl), are characterized using Trp and 5-fluoroTrp (5-FTrp) fluorescence spectroscopy. The four positions, 97, 114, 126, and 133, are located in a region shown by recent studies to be involved in the mannitol...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi8020668

    authors: Vos EP,Bokhove M,Hesp BH,Broos J

    更新日期:2009-06-16 00:00:00

  • Compound I radical in site-directed mutants of cytochrome c peroxidase as probed by electron paramagnetic resonance and electron-nuclear double resonance.

    abstract::The reaction of ferric cytochrome c peroxidase (CcP) from Saccharomyces cerevisiae with peroxide produces compound I, characterized by both an oxyferryl iron center and a protein-based free radical. The electron paramagnetic resonance (EPR) signal of the CcP compound I radical can be resolved into a broad majority com...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00221a036

    authors: Fishel LA,Farnum MF,Mauro JM,Miller MA,Kraut J,Liu YJ,Tan XL,Scholes CP

    更新日期:1991-02-19 00:00:00

  • Flexibility and bioactivity of insulin: an NMR investigation of the solution structure and folding of an unusually flexible human insulin mutant with increased biological activity.

    abstract::The structure and folding of a novel human insulin mutant, [Thr(B27) --> Pro, Pro(B28) --> Thr]insulin (PT insulin), in aqueous solution and in mixtures of water and 2,2,2-trifluoroethanol (TFE) have been studied by NMR spectroscopy. It was found that PT insulin has a highly flexible structure in pure water and is pre...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi0108150

    authors: Keller D,Clausen R,Josefsen K,Led JJ

    更新日期:2001-09-04 00:00:00

  • Altered APP processing in PDAPP (Val717 --> Phe) transgenic mice yields extended-length Abeta peptides.

    abstract::Central to the pathology of Alzheimer's disease (AD) is the profuse accumulation of amyloid-beta (Abeta) peptides in the brain of affected individuals, and several amyloid precursor protein (APP) transgenic (Tg) mice models have been created to mimic Abeta deposition. Among these, the PDAPP Tg mice carrying the famili...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi051213+

    authors: Esh C,Patton L,Kalback W,Kokjohn TA,Lopez J,Brune D,Newell AJ,Beach T,Schenk D,Games D,Paul S,Bales K,Ghetti B,Castaño EM,Roher AE

    更新日期:2005-10-25 00:00:00

  • Characterization and stereochemistry of cofactor oxidation by a type II dihydrofolate reductase.

    abstract::Type II dihydrofolate reductases (DHFRs) encoded by the R67 and R388 plasmids are different both in sequence and in structure from known chromosomal DHFRs. These plasmid-derived DHFRs are responsible for conferring trimethoprim resistance to the host strain. A derivative of R388 DHFR, RBG200, has been cloned and overp...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00494a011

    authors: Brito RM,Reddick R,Bennett GN,Rudolph FB,Rosevear PR

    更新日期:1990-10-23 00:00:00

  • Membrane interactions of mutated forms of the influenza fusion peptide.

    abstract::We have studied a group of fusion peptides of influenza hemagglutinin in which the N-terminal amino acid, Gly (found in the wild-type peptide), has been systematically substituted with Ala, Ser, Val, or Glu. The activity of the intact hemagglutinin protein with these same substitutions has already been reported. As a ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi0107187

    authors: Epand RM,Epand RF,Martin I,Ruysschaert JM

    更新日期:2001-07-31 00:00:00

  • Effect of pressure on deuterium isotope effects of yeast alcohol dehydrogenase: evidence for mechanical models of catalysis.

    abstract::Moderate pressure accelerates hydride transfer catalyzed by yeast alcohol dehydrogenase, indicative of a large negative volume of activation [Cho and Northrop (1999) Biochemistry 38, 7470-7475]. A comparison of the effects of pressure on the oxidation of normal versus dideuteriobenzyl alcohol generates a monophasic de...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi992537z

    authors: Northrop DB,Cho YK

    更新日期:2000-03-07 00:00:00

  • Interaction of lipoprotein lipase with phospholipid vesicles: effect on protein and lipid structure.

    abstract::The interaction of lipoprotein lipase (LpL) and a nonhydrolyzable phosphatidylcholine, 1,2-ditetradecyl-rac-glycero-3-phosphocholine (C14-ether-PC), has been studied by several physical methods. Analysis of the circular dichroic spectrum of LpL gave the following fractional conformation: 35% alpha-helix, 30% beta-plea...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00352a020

    authors: McLean LR,Larsen WJ,Jackson RL

    更新日期:1986-02-25 00:00:00

  • Influence of the extent of branching on solution conformations of complex oligosaccharides: a molecular dynamics and NMR study of a penta-antennary "bisected" N-glycan.

    abstract::The solution conformation of an agalactosyl penta-antennary "bisected" N-linked glycan from hen ovomucoid has been determined using a combination of 1H-NMR NOE measurements and restrained molecular dynamics (MD) simulations. The majority of glycosidic linkages exhibited restricted torsional fluctuations about the glob...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00043a018

    authors: Rutherford TJ,Neville DC,Homans SW

    更新日期:1995-10-31 00:00:00

  • Structural, Functional, and Dynamical Responses of a Protein in a Restricted Environment Imposed by Macromolecular Crowding.

    abstract::The intercellular environment is known to be very different from the environment where most of the elementary biological processes are studied in the laboratory. As a result, there was a considerable effort on cell mimicking either by confinement or by introducing macromolecular crowding. In the present study, dextran...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/acs.biochem.8b00599

    authors: Das N,Sen P

    更新日期:2018-10-23 00:00:00

  • Thermal denaturation of spinach plastocyanin: effect of copper site oxidation state and molecular oxygen.

    abstract::The thermal denaturation of the cupredoxin plastocyanin (PC) from spinach has been studied with the aim of improving the understanding of factors involved in the conformational stability of antiparallel beta-sheet proteins. Studies using differential scanning calorimetry have been complemented with nuclear magnetic re...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi034371e

    authors: Sandberg A,Harrison DJ,Karlsson BG

    更新日期:2003-09-02 00:00:00

  • Rapid and reversible inhibition of aquaporin-4 by zinc.

    abstract::Aquaporin-4 (AQP4) is the predominant water channel in the brain. Although AQP4 plays an important role in brain water homeostasis, the molecular mechanisms of AQP4 regulation are not fully understood. In this report, we show how Zn(2+) rapidly and reversibly decreases the water permeability of AQP4 when it is reconst...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi901762y

    authors: Yukutake Y,Hirano Y,Suematsu M,Yasui M

    更新日期:2009-12-29 00:00:00

  • Topography of the Dictyostelium discoideum plasma membrane: analysis of membrane asymmetry and intermolecular disulfide bonds.

    abstract::Through the application of a unique method for isolating plasma membranes, it was possible to specifically iodinate cytoplasm-exposed plasma membrane proteins in vegetative cells of the cellular slime mold Dictyostelium discoideum. The original procedure [Chaney, L. K., & Jacobson, B. S. (1983) J. Biol. Chem. 258, 100...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00389a041

    authors: Shiozawa JA,Jelenska MM,Jacobson BS

    更新日期:1987-07-28 00:00:00

  • Homogeneity and variability in the structure of azurin molecules studied by fluorescence decay and circular polarization.

    abstract::The fluorescence decay of apoazurin derived from Pseudomonas aeruginosa is monoexponential. By this criterion the population of molecules of apoazurin is homogeneous. The emission anisotropy factor and the absorption anisotropy factor at the red edge of the absorption band assume similar values, showing that the trypt...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00680a018

    authors: Grinvald A,Schlessinger J,Pecht I,Steinberg IZ

    更新日期:1975-05-06 00:00:00

  • Truncation of the amino terminus of human apolipoprotein A-I substantially alters only the lipid-free conformation.

    abstract::An amino-terminal deletion mutant (residues 1-43) of human apolipoprotein A-I (apo hA-I) has been produced from a bacterial expression system to explore the structural and functional role of these amino acids, encoded by exon 3, in apo hA-I. Lipid binding of apo delta (1-43)A-I and lipid binding of apo hA-I are very s...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi961876e

    authors: Rogers DP,Brouillette CG,Engler JA,Tendian SW,Roberts L,Mishra VK,Anantharamaiah GM,Lund-Katz S,Phillips MC,Ray MJ

    更新日期:1997-01-14 00:00:00