Role of tryptophanyl and tyrosyl residues of flavoproteins in binding with flavin coenzymes. X-ray structural studies using model complexes.

Abstract:

:The crystal structures of 7,8-dimethylisoalloxazine-10-acetic acid-tryptamine (1:1) tetrahydrate and 7,8-dimethylisoalloxazine-10-acetic acid-tyramine (1:1) tetrahydrate complexes were determined by the X-ray diffraction method, as models for flavin-tryptophan and flavin-tyrosine interactions in flavoproteins. The observed parallel stackings and the intermolecular spacing distances, which were less than the normal van der Waals separation between the isoalloxazine and indole rings and between the isoalloxazine and phenol rings, suggest the existence of charge-transfer interactions in their ground states. The indole and phenol rings interact with the pyrimindinoid and pyrazinoid portions of the isoalloxazine ring and have short contacts, less than 3.4 A, with the reduction site (N1 and N5 atoms) of this ring. This suggests that the reduction of oxidized flavin to the semiquinone state may be facilitated by charge transfer from the former rings to the N1 and N5 atoms. Absorption difference spectra showed that both complexes associate with equimolar ratios in solution as well as in the crystalline state and that they have the same charge-transfer bands and association constants as flavin mononucleotide (FMN)-Trp and FMN-Tyr complexes, respectively. On the other hand, proton magnetic resonance spectra suggested that in solution, the stacking modes of the indole and phenol rings to the isoalloxazine ring are different from those observed in the crystal structures and both aromatic rings are stacked over the whole of the isoalloxazine ring.

journal_name

Biochemistry

journal_title

Biochemistry

authors

Inoue M,Shibata M,Kondo Y,Ishida T

doi

10.1021/bi00513a034

subject

Has Abstract

pub_date

1981-05-12 00:00:00

pages

2936-45

issue

10

eissn

0006-2960

issn

1520-4995

journal_volume

20

pub_type

杂志文章
  • Cyclic peptides incorporating 4-carboxyphenylalanine and phosphotyrosine are potent inhibitors of pp60(c-)(src).

    abstract::The protein tyrosine kinase, pp60(c-)(src), is involved in cellular signaling and is activated during mitosis and in various tumors. We have been employing cyclic decapeptides to identify the determinants for substrate binding and phosphorylation to develop inhibitors competitive with protein substrates of Src. A stru...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi992994f

    authors: Wang W,Ramdas L,Sun G,Ke S,Obeyesekere NU,Budde RJ,McMurray JS

    更新日期:2000-05-02 00:00:00

  • Selective cytotoxicity of rhodium metalloinsertors in mismatch repair-deficient cells.

    abstract::Mismatches in DNA occur naturally during replication and as a result of endogenous DNA damaging agents, but the mismatch repair (MMR) pathway acts to correct mismatches before subsequent rounds of replication. Rhodium metalloinsertors bind to DNA mismatches with high affinity and specificity and represent a promising ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi2015822

    authors: Ernst RJ,Komor AC,Barton JK

    更新日期:2011-12-20 00:00:00

  • Solution structure of the (+)-cis-anti-benzo[a]pyrene-dA ([BP]dA) adduct opposite dT in a DNA duplex.

    abstract::Minor adducts, derived from the covalent binding of anti-benzo[a]pyrene-7,8-dihydroxy-9,10-epoxide to cellular DNA, may play an important role in generating mutations and initiating cancer. We have applied a combined NMR-computational approach including intensity based refinement to determine the solution structure of...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi991212f

    authors: Mao B,Gu Z,Gorin A,Chen J,Hingerty BE,Amin S,Broyde S,Geacintov NE,Patel DJ

    更新日期:1999-08-17 00:00:00

  • DNA hairpin structures in solution: 500-MHz two-dimensional 1H NMR studies on d(CGCCGCAGC) and d(CGCCGTAGC).

    abstract::A hairpin structure contains two conformationally distinct domains: a double-helical stem with Watson-Crick base pairs and a single-stranded loop that connects the two arms of the stem. By extensive 1D and 2D 500-MHz 1H NMR studies in H2O and D2O, it has been demonstrated that the DNA oligomers d(CGCCGCAGC) and d(CGCC...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00398a027

    authors: Gupta G,Sarma MH,Sarma RH,Bald R,Engelke U,Oei SL,Gessner R,Erdmann VA

    更新日期:1987-12-01 00:00:00

  • Thermodynamics and specificity of the Mbp1-DNA interaction.

    abstract::The DNA binding domain of the yeast transcription factor Mbp1 is a winged helix-turn-helix structure, with an extended DNA binding site involving C-terminal "tail" residues. The thermodynamics of the interaction of the DNA binding domain with its target DNA sequence have been determined using fluorescence anisotropy a...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi702339q

    authors: Deleeuw L,Tchernatynskaia AV,Lane AN

    更新日期:2008-06-17 00:00:00

  • Integrin-supported fast rate intracellular delivery of plasmid DNA by extracellular matrix protein embedded calcium phosphate complexes.

    abstract::Extracellular matrix (ECM) proteins, such as collagen and fibronectin, play vital roles in development and maintenance of hard tissue (bone or tooth) and are, consequently, thoroughly investigated for construction of biomimetic scaffolds in combination with calcium phosphate (CaP) material (the major component of hard...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi050595g

    authors: Chowdhury EH,Nagaoka M,Ogiwara K,Zohra FT,Kutsuzawa K,Tada S,Kitamura C,Akaike T

    更新日期:2005-09-20 00:00:00

  • Triple helix forming TRIPside molecules that target mixed purine/pyrimidine DNA sequences.

    abstract::A new strategy to form stable and sequence-specific triple helical DNA structures at mixed purine/pyrimidine sequences using a combination of four C-glycosides (TRIPsides) has been described [Li et al. (2003) J. Am. Chem. Soc. 125, 2084]. The partial realization of the approach is demonstrated by incorporating two of ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi035648d

    authors: Li JS,Shikiya R,Marky LA,Gold B

    更新日期:2004-02-17 00:00:00

  • Biochemical characterization of the minichromosome maintenance (MCM) protein of the crenarchaeote Aeropyrum pernix and its interactions with the origin recognition complex (ORC) proteins.

    abstract::Replication in archaea is carried out by proteins that are homologues of eukaryotic counterparts. However, the archaeal systems tend to be much simpler with fewer different genes encoding the core functions than in eukaryotic counterparts. In many archaea, there is a single minichromosome maintenance (MCM) homologue, ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi801479s

    authors: Atanassova N,Grainge I

    更新日期:2008-12-16 00:00:00

  • Site of action and biphasic effect of neutral salts in the phosphorylase kinase reaction.

    abstract::The inhibition of phosphorylase kinase catalytic activity by 0.1 M neutral salts was predicted by the Hofmeister series of anions. The site of action of the salts was determined by the following evidence to be on the phosphorylase kinase molecule directly, rather than on its protein substrate. (1) Nonactivated kinase ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00665a022

    authors: Carlson GM,Graves DJ

    更新日期:1976-10-05 00:00:00

  • Catalytic mechanism of enterococcal kanamycin kinase (APH(3')-IIIa): viscosity, thio, and solvent isotope effects support a Theorell-Chance mechanism.

    abstract::Bacterial resistance to the aminoglycoside antibiotics is manifested primarily through the production of enzymes which covalently modify these drugs. The Enterococci and Staphylococci produce an ATP-dependent kinase, APH(3')-IIIa, which phosphorylates such antibiotics as kanamycin, amikacin, and neomycin, and this enz...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi9603884

    authors: McKay GA,Wright GD

    更新日期:1996-07-02 00:00:00

  • Nearest neighbor analysis of the SecYEG complex. 2. Identification of a SecY-SecE cytosolic interface.

    abstract::Although the importance of interactions involving both the cytosolic and transmembrane regions of SecY and SecE has been documented, no information has been available for the physical contact sites of these translocase subunits in their cytosolic domains. We now carried out site-specific cross-linking experiments to i...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi034333v

    authors: Satoh Y,Mori H,Ito K

    更新日期:2003-06-24 00:00:00

  • Homodinuclear (Pt,Pt) and heterodinuclear (Ru,Pt) metal compounds as DNA-protein cross-linking agents: potential suicide DNA lesions.

    abstract::Homodinuclear (Pt,Pt) and heterodinuclear (Ru,Pt) metal compounds having the generalized formula M(a)NH2(CH)4NH2M(b) are shown to form specific DNA lesions which can efficiently cross-link proteins to DNA. In this study, the homodinuclear case is represented by M(a) = M(b) = [cis-Pt(Cl2)-(NH3)] and the heterodinuclear...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00095a007

    authors: Van Houten B,Illenye S,Qu Y,Farrell N

    更新日期:1993-11-09 00:00:00

  • NSC 622124 inhibits human Eg5 and other kinesins via interaction with the conserved microtubule-binding site.

    abstract::Kinesin-5 proteins are essential for formation of a bipolar mitotic spindle in most and, perhaps all, eukaryotic cells. Several Kinesin-5 proteins, notably the human version, HsEg5, are targets of a constantly expanding group of small-molecule inhibitors, which hold promise both as tools for probing mechanochemical tr...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi801291q

    authors: Learman SS,Kim CD,Stevens NS,Kim S,Wojcik EJ,Walker RA

    更新日期:2009-03-03 00:00:00

  • Inhibition of T cell signaling by immunophilin-ligand complexes correlates with loss of calcineurin phosphatase activity.

    abstract::Calcineurin, a Ca2+, calmodulin-dependent protein phosphatase, was recently found to bind with high affinity to two different immunosuppressant binding proteins (immunophilins) with absolute dependence on the presence of the immunosuppressants FK506 or cyclosporin A (CsA) [Liu et al. (1991) Cell 66, 807-815]. The bind...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00131a002

    authors: Liu J,Albers MW,Wandless TJ,Luan S,Alberg DG,Belshaw PJ,Cohen P,MacKintosh C,Klee CB,Schreiber SL

    更新日期:1992-04-28 00:00:00

  • Skp Trimer Formation Is Insensitive to Salts in the Physiological Range.

    abstract::Biogenesis of the Gram-negative outer membrane involves the chaperone seventeen kilodalton protein (Skp). A Skp trimer is currently thought to bind its unfolded outer membrane protein (uOMP) substrates. Using sedimentation equilibrium, we discovered that Skp is not an obligate trimer under physiological conditions and...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/acs.biochem.5b00806

    authors: Sandlin CW,Zaccai NR,Fleming KG

    更新日期:2015-12-08 00:00:00

  • The role of phenylalanine 31 in maintaining the conformational stability of ribonuclease P2 from Sulfolobus solfataricus under extreme conditions of temperature and pressure.

    abstract::Ribonuclease P2 from the thermophilic archaebacterium Sulfolobus solfataricus is a small protein (7 kDa) with a known three-dimensional structure. Inspection of the structure and molecular dynamics simulation reveal that three aromatic residues (Phe5, Phe31, and Tyr33) from the hydrophobic core have a strong van der W...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi970467v

    authors: Mombelli E,Afshar M,Fusi P,Mariani M,Tortora P,Connelly JP,Lange R

    更新日期:1997-07-22 00:00:00

  • Association of insulin-like growth factor 2 with the insulin-linked polymorphic region in cultured fetal thymus cells.

    abstract::The insulin-linked polymorphic region (ILPR) is a regulatory sequence in the promoter region upstream of the human insulin gene and is widely recognized as a locus of type 1 diabetes susceptibility. Polymorphism of the ILPR sequence can affect expression of both insulin and the adjacent insulin-like growth factor 2 (I...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi900958x

    authors: Wang Y,Zhang H,Ligon LA,McGown LB

    更新日期:2009-09-01 00:00:00

  • Dissection of the pH dependence of inhibitor binding energetics for an aspartic protease: direct measurement of the protonation states of the catalytic aspartic acid residues.

    abstract::The catalytic activity and inhibitor binding energetics of enzymes are often pH-dependent properties. Aspartic proteases comprise an important class of enzyme targets for structure-based drug design. We have performed a complete thermodynamic study of pepstatin binding to plasmepsin II, an aspartic proteinase found in...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi971550l

    authors: Xie D,Gulnik S,Collins L,Gustchina E,Suvorov L,Erickson JW

    更新日期:1997-12-23 00:00:00

  • Activation of polyisoprenyl diphosphate phosphatase 1 remodels cellular presqualene diphosphate.

    abstract::Polyisoprenyl diphosphates play diverse and vital roles in cell function in health and disease. The counter-regulatory lipid signaling molecule, presqualene diphosphate (PSDP), is rapidly converted to its monophosphate form (PSMP) upon cell activation [Levy, B. D., Petasis, N. A., and Serhan, C. N. (1997) Nature 389, ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi8020636

    authors: Carlo T,Petasis NA,Levy BD

    更新日期:2009-04-07 00:00:00

  • Intrinsic flexibility of West Nile virus protease in solution characterized using small-angle X-ray scattering.

    abstract::West Nile virus (WNV) is a mosquito-borne flavivirus with a rapidly expanding global distribution. Infection can cause severe neurological disease and fatality in humans. Efforts are ongoing to develop antiviral drugs that inhibit the WNV protease, a viral enzyme required for polyprotein processing. Unfortunately, lit...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi400782w

    authors: Garces AP,Watowich SJ

    更新日期:2013-10-01 00:00:00

  • Replacement of a conserved proline and the alkaline conformational change in iso-2-cytochrome c.

    abstract::Although point mutations usually lead to minor localized changes in protein structure, replacement of conserved Pro-76 with Gly in iso-2-cytochrome c induces a major conformational change. The change in structure results from mutation-induced depression of the pK for transition to an alkaline conformation with altered...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00451a043

    authors: Nall BT,Zuniga EH,White TB,Wood LC,Ramdas L

    更新日期:1989-12-12 00:00:00

  • Cavities in proteins: structure of a metmyoglobin-xenon complex solved to 1.9 A.

    abstract::X-ray crystallographic data to 1.9-A resolution were collected on sperm whale metmyoglobin equilibrated with 7 atm of xenon gas. The results indicate four xenon sites of occupancy from 0.45 to 1.0. These sites are located in interior spaces or packing defects of the myoglobin molecule. The effects of the bound xenon o...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00308a002

    authors: Tilton RF Jr,Kuntz ID Jr,Petsko GA

    更新日期:1984-06-19 00:00:00

  • A proton nuclear magnetic resonance study of the quaternary structure of human homoglobins in water.

    abstract::Proton nuclear magnetic resonance spectra of human hemoglobins in water reveal several exchangeable protons which are indicators of the quaternary structures of both the liganded and unliganded molecules. A comparison of the spectra of normal human adult hemoglobin with those of mutant hemoglobins Chesapeake (FG4alpha...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00682a036

    authors: Fung LW,Ho C

    更新日期:1975-06-03 00:00:00

  • Essential sulfhydryl for reduced nicotinamide adenine dinucleotide binding in D-beta-hydroxybutyrate dehydrogenase.

    abstract::Chemical derivatization studies have been directed at the sulfhydryl group of D-beta-hydroxybutyrate dehydrogenase, a lipid-requiring enzyme. Reaction with N-ethylmaleimide leads to progressive and parallel loss of both enzymic activity and coenzyme binding. Both functions are lost when 1 equiv of sulfhydryl is deriva...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00564a021

    authors: Latruffe N,Brenner SC,Fleischer S

    更新日期:1980-11-11 00:00:00

  • Disrupted zinc-binding sites in structures of pathogenic SOD1 variants D124V and H80R.

    abstract::Mutations in human copper-zinc superoxide dismutase (SOD1) cause an inherited form of the fatal neurodegenerative disease amyotrophic lateral sclerosis (ALS). Here, we present structures of the pathogenic SOD1 variants D124V and H80R, both of which demonstrate compromised zinc-binding sites. The disruption of the zinc...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi100314n

    authors: Seetharaman SV,Winkler DD,Taylor AB,Cao X,Whitson LJ,Doucette PA,Valentine JS,Schirf V,Demeler B,Carroll MC,Culotta VC,Hart PJ

    更新日期:2010-07-13 00:00:00

  • Isolation and characterization of independently folding regions of the beta chain of Escherichia coli tryptophan synthetase.

    abstract::It had been reported previously that the beta2 subunit of Escherichia coli tryptophan synthetase [L-serinehydrolyase (adding indole) EC 4.2.1.20] can be cleaved by trypsin into a nearly functional dimeric protein, the monomer of which consists of two large, nonoverlapping, polypeptide fragments. In the present paper, ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00637a012

    authors: Högberg-Raibaud A,Goldberg ME

    更新日期:1977-09-06 00:00:00

  • Evidence for a tRNA/rRNA interaction site within the peptidyltransferase center of the Escherichia coli ribosome.

    abstract::A nine-base oligodeoxyribonucleotide complementary to bases 2497-2505 of 23S rRNA was hybridized to both 50S subunits and 70S ribosomes. The binding of the probe to the ribosome or ribosomal subunits was assayed by nitrocellulose filtration and by sucrose gradient centrifugation techniques. The location of the hybridi...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00428a073

    authors: Marconi RT,Hill WE

    更新日期:1989-01-24 00:00:00

  • Mechanism of the orotidine 5'-monophosphate decarboxylase-catalyzed reaction: importance of residues in the orotate binding site.

    abstract::The reaction catalyzed by orotidine 5'-monophosphate decarboxylase (OMPDC) is accompanied by exceptional values for rate enhancement (k(cat)/k(non) = 7.1 × 10(16)) and catalytic proficiency [(k(cat)/K(M))/k(non) = 4.8 × 10(22) M(-1)]. Although a stabilized vinyl carbanion/carbene intermediate is located on the reactio...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi2012355

    authors: Iiams V,Desai BJ,Fedorov AA,Fedorov EV,Almo SC,Gerlt JA

    更新日期:2011-10-04 00:00:00

  • Regulation of 3-hydroxy-3-methylglutaryl coenzyme A reductase activity and the esterification of cholesterol in human long term lymphoid cell lines.

    abstract::The regulation of the rate-controlling enzyme in cholesterol biosynthesis and of the incorporation of [14C]oleate into cholesterol esters were studied in established lymphoid cell lines from normal subjects and compared with that of eight patients with genetic abnormalities of lipid metabolism. The activity of 3-hydro...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00648a011

    authors: Kayden HJ,Hatam L,Beratis NG

    更新日期:1976-02-10 00:00:00

  • Engineering a novel specificity in subtilisin BPN'.

    abstract::The specificity of subtilisin BPN' toward substrates with large hydrophobic P4 residues has been improved by single amino acid replacements at positions 104 and 107. Mutations were designed to (i) increase the size of the P4 binding pocket by replacing Ile107, which is at the bottom of the S4 pocket, by Val, Ala, and ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00056a001

    authors: Rheinnecker M,Baker G,Eder J,Fersht AR

    更新日期:1993-02-09 00:00:00