Structural requirements for formyl homooligopeptide chemoattractants.

Abstract:

:Using solution peptide synthesis, we have made three series of N alpha-formylated homooligopeptides, from the dipeptide to the heptapeptide, derived from L-methionine, L-norleucine, and S-methyl-L-cysteine and related to the chemotactic peptide N alpha-formylmethionylleucylphenylalanine. Compounds were prepared to determine the combined effects of the main-chain length and the presence of a sulfur atom in side-chain gamma- and delta-positions. Each peptide was tested for its ability to induce rabbit peritoneal polymorphonuclear leukocytes in the presence of cytochalasin B to secrete granule enzymes. In parallel, a conformational analysis was carried out in the solid state and in solution, using infrared absorption and circular dichroism. We examined these peptides in solvents of widely different polarities, i.e., chloroform, 2,2,2-trifluoroethanol, 1,1,1,3,3,3-hexafluoropropan-2-ol, and mixed organic-aqueous media. The tendencies to form antiparallel-chain beta-associated and folded structures were determined. The biological and conformational data are described in terms of a model of the chemotactic peptide receptor of rabbit neutrophils recently proposed by Freer et al. (1982) [Freer, R.J., Day, A.R., Muthukumarswamy, N., Pinon, D., Wu, A., Showell, H.J., & Becker, E.L. (1982) Biochemistry 21, 257-263]. In the three N alpha-formylated C-methoxy homooligopeptide series tested, the highest level of activity attained is at the tetrapeptide or pentapeptide stage, confirming the suggestion that the formylpeptide receptor is large enough to accommodate a peptide with at least four amino acid residues.(ABSTRACT TRUNCATED AT 250 WORDS)

journal_name

Biochemistry

journal_title

Biochemistry

authors

Toniolo C,Bonora GM,Showell H,Freer RJ,Becker EL

doi

10.1021/bi00299a018

subject

Has Abstract

pub_date

1984-02-14 00:00:00

pages

698-704

issue

4

eissn

0006-2960

issn

1520-4995

journal_volume

23

pub_type

杂志文章
  • 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

  • Differential regulation of WASP and N-WASP by Cdc42, Rac1, Nck, and PI(4,5)P2.

    abstract::The Wiskott-Aldrich syndrome protein (WASP) and neural WASP (N-WASP) are key players in regulating actin cytoskeleton via the Arp2/3 complex. It has been widely reported that the WASP proteins are activated by Rho family small GTPase Cdc42 and that Rac1 acts through SCAR/WAVE proteins. However, a systematic study of t...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi062152y

    authors: Tomasevic N,Jia Z,Russell A,Fujii T,Hartman JJ,Clancy S,Wang M,Beraud C,Wood KW,Sakowicz R

    更新日期:2007-03-20 00:00:00

  • Tryptophan B27 in the relaxin-like factor (RLF) is crucial for RLF receptor-binding.

    abstract::The relaxin-like factor (RLF) is a circulating hormone that is synthesized in the gonads of mammals and released into the bloodstream. The distribution of its receptor and a trace of cross-reactivity to relaxin receptors implied that this relatively new factor is more relaxin- than insulin-like. The chemical synthesis...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi982687u

    authors: Büllesbach EE,Schwabe C

    更新日期:1999-03-09 00:00:00

  • Insight into the mechanism of phosphoenolpyruvate mutase catalysis derived from site-directed mutagenesis studies of active site residues.

    abstract::PEP mutase catalyzes the conversion of phosphoenolpyruvate (PEP) to phosphonopyruvate in biosynthetic pathways leading to phosphonate secondary metabolites. A recent X-ray structure [Huang, K., Li, Z., Jia, Y., Dunaway-Mariano, D., and Herzberg, O. (1999) Structure (in press)] of the Mytilus edulis enzyme complexed wi...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi990771j

    authors: Jia Y,Lu Z,Huang K,Herzberg O,Dunaway-Mariano D

    更新日期:1999-10-26 00:00:00

  • Delineation of an active fragment and poly(L-proline) II conformation for candidacidal activity of bactenecin 5.

    abstract::Bactenecin 5 and its fragments [BN22 (1-22), BN16 (7-22), and BC24 (20-43)] were synthesized by solid-phase methods. Their antifungal activities on Candida albicans have been studied and compared with those of the native bactenecin 5. The conformational preferences of these peptides in aqueous and nonaqueous solutions...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi951681r

    authors: Raj PA,Marcus E,Edgerton M

    更新日期:1996-04-09 00:00:00

  • Properties of Paracoccus denitrificans amicyanin.

    abstract::Paracoccus denitrificans synthesizes an inducible, periplasmic, blue copper protein [Husain, M., & Davidson, V.L. (1985) J. Biol. Chem. 260, 14626-14629] that can be classified as an amicyanin on the basis of its ability to accept electrons from methylamine dehydrogenase. The amino acid composition and sequence of the...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00357a020

    authors: Husain M,Davidson VL,Smith AJ

    更新日期:1986-05-06 00:00:00

  • Conformation of peptide fragments of proteins in aqueous solution: implications for initiation of protein folding.

    abstract::Applications of sensitive new technologies, in particular, two-dimensional NMR spectroscopy, have allowed detection of folded structures in short peptide fragments of proteins in aqueous solution under conditions where native proteins fold. These structures are in rapid dynamic exchange with unfolded states. These obs...

    journal_title:Biochemistry

    pub_type: 杂志文章,评审

    doi:10.1021/bi00419a001

    authors: Wright PE,Dyson HJ,Lerner RA

    更新日期:1988-09-20 00:00:00

  • NMR structure determination of a novel conotoxin, [Pro 7,13] alpha A-conotoxin PIVA.

    abstract::A high-resolution solution conformation of a novel conotoxin, [Pro 7,13] alpha A-conotoxin PIVA, GCCGSYPNAACHPCSCKDROSYCGQ-NH2, has been determined by two-dimensional 1H NMR methods and distance geometry calculations. The total of 324 NOE-derived interproton distance restraints including 33 long-range NOE restraints a...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi962301k

    authors: Han KH,Hwang KJ,Kim SM,Kim SK,Gray WR,Olivera BM,Rivier J,Shon KJ

    更新日期:1997-02-18 00:00:00

  • Inhibition of sodium-calcium exchange in cardiac sarcolemmal membrane vesicles. 1. Mechanism of inhibition by amiloride analogues.

    abstract::The mechanism by which terminal guanidino nitrogen substituted analogues of amiloride inhibit Na-Ca exchange in purified cardiac sarcolemmal membrane vesicles has been investigated. These inhibitors block both Nai-dependent Ca2+ uptake and Nao-dependent Ca2+ efflux. Inhibition of Na-Ca exchange monitored in K+ is nonc...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00407a023

    authors: Slaughter RS,Garcia ML,Cragoe EJ Jr,Reeves JP,Kaczorowski GJ

    更新日期:1988-04-05 00:00:00

  • The FinO repressor of bacterial conjugation contains two RNA binding regions.

    abstract::Conjugative transfer of F-like plasmids in Escherichia coli is repressed by a plasmid-encoded protein, FinO. FinO blocks the translation of TraJ, a positive activator of transcription of genes required for conjugation. FinO binds a traJ antisense RNA, FinP, thereby protecting it from degradation, and catalyzes FinP-tr...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi9911482

    authors: Ghetu AF,Gubbins MJ,Oikawa K,Kay CM,Frost LS,Glover JN

    更新日期:1999-10-19 00:00:00

  • Interactions of mycobacterial glycopeptidolipids with membranes: influence of carbohydrate on induced alterations.

    abstract::Glycopeptidolipids (GPLs) are specific constituents of mycobacteria known as opportunistic pathogens. The influence of the carbohydrate moiety on GPL-induced membrane alterations was examined with GPLs bearing 1-5 sugar residues (GPL-1 to GPL-5) and a sulfated GPL (S-GPL-2). GPLs decreased the ADP/O ratio and increase...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00189a006

    authors: Lopez-Marin LM,Quesada D,Lakhdar-Ghazal F,Tocanne JF,Lanéelle G

    更新日期:1994-06-14 00:00:00

  • Metal-induced changes in the fluorescence properties of tyrosine and tryptophan site-specific mutants of oncomodulin.

    abstract::Oncomodulin is a 108-residue, oncodevelopmental protein containing two calcium-binding sites identified as the CD- and EF-loops. The protein contains no tryptophan and only two tyrosine residues, one which is a calcium ligand in the CD-loop (Tyr-57) and one which lies in the flanking D-helix of this loop (Tyr-65). Sit...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00244a038

    authors: Hutnik CM,MacManus JP,Banville D,Szabo AG

    更新日期:1991-07-30 00:00:00

  • Fe protein-independent substrate reduction by nitrogenase MoFe protein variants.

    abstract::The reduction of substrates catalyzed by nitrogenase normally requires nucleotide-dependent Fe protein delivery of electrons to the MoFe protein, which contains the active site FeMo cofactor. Here, it is reported that independent substitution of three amino acids (β-98(Tyr→His), α-64(Tyr→His), and β-99(Phe→His)) locat...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/acs.biochem.5b00140

    authors: Danyal K,Rasmussen AJ,Keable SM,Inglet BS,Shaw S,Zadvornyy OA,Duval S,Dean DR,Raugei S,Peters JW,Seefeldt LC

    更新日期:2015-04-21 00:00:00

  • Three-dimensional structures of the amyloid beta peptide (25-35) in membrane-mimicking environment.

    abstract::The three-dimensional structure of amyloid beta peptide (25-35), which has neurotoxic activity, in lithium dodecyl sulfate micelles was determined by two-dimensional 1H NMR spectroscopy with simulated annealing calculations. A total of 20 converged amyloid beta peptide structures were obtained on the basis of 110 expe...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi961598j

    authors: Kohno T,Kobayashi K,Maeda T,Sato K,Takashima A

    更新日期:1996-12-17 00:00:00

  • Crystallographic Structures of IlvN·Val/Ile Complexes: Conformational Selectivity for Feedback Inhibition of Aceto Hydroxy Acid Synthases.

    abstract::Conformational factors that predicate selectivity for valine or isoleucine binding to IlvN leading to the regulation of aceto hydroxy acid synthase I (AHAS I) of Escherichia coli have been determined for the first time from high-resolution (1.9-2.43 Å) crystal structures of IlvN·Val and IlvN·Ile complexes. The valine ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/acs.biochem.9b00050

    authors: Bansal A,Karanth NM,Demeler B,Schindelin H,Sarma SP

    更新日期:2019-04-16 00:00:00

  • A mechanism for reducing entropic cost of induced fit in protein--RNA recognition.

    abstract::Induced fit has been postulated to be an important component of ligand interactions with proteins, including protein-DNA interactions. We imagined that the entropic cost of induced fit might be highly dependent on the local protein sequence context around critical contact residues. To investigate this question, we ana...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi960256a

    authors: Ribas de Pouplana L,Auld DS,Kim S,Schimmel P

    更新日期:1996-06-25 00:00:00

  • Factors affecting gamma-chain multimer formation in cross-linked fibrin.

    abstract::The major covalently linked multimolecular D fragments found in plasmic digests of factor XIIIa cross-linked fibrin formed under physiological pH and ionic strength conditions consist of D dimers, D trimers, and D tetramers. These fragments are linked by epsilon-amino-gamma-glutamyllysine bonds in the carboxy-terminal...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00118a040

    authors: Siebenlist KR,Mosesson MW

    更新日期:1992-01-28 00:00:00

  • Disulfide-linked bovine beta-lactoglobulin dimers fold slowly, navigating a glassy folding landscape.

    abstract::To gain insight into the folding of large proteins, we constructed a bovine beta-lactoglobulin (beta-lg) dimeric mutant, A34C/C121A beta-lg. In the mutant, a free thiol group of wild-type beta-lg at Cys121 was removed and two beta-lg molecules were linked by a disulfide bridge through Cys34 created at the dimer's inte...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi8001715

    authors: Yagi M,Kameda A,Sakurai K,Nishimura C,Goto Y

    更新日期:2008-06-03 00:00:00

  • Ligand migration and binding in nonsymbiotic hemoglobins of Arabidopsis thaliana.

    abstract::We have studied carbon monoxide (CO) migration and binding in the nonsymbiotic hemoglobins AHb1 and AHb2 of Arabidopsis thaliana using Fourier transform infrared (FTIR) spectroscopy combined with temperature derivative spectroscopy (TDS) at cryogenic temperatures. Both proteins have similar amino acid sequences but di...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi100768g

    authors: Nienhaus K,Dominici P,Astegno A,Abbruzzetti S,Viappiani C,Nienhaus GU

    更新日期:2010-09-07 00:00:00

  • Structure of a hydroxyl radical induced DNA-protein cross-link involving thymine and tyrosine in nucleohistone.

    abstract::Hydroxyl radical induced formation of a DNA-protein cross-link involving thymine and tyrosine in nucleohistone is described. Hydroxyl radicals were generated in N2O-saturated aqueous solution by ionizing radiation. Samples of nucleohistone were hydrolyzed with HCl and trimethylsilylated. Analysis of irradiated samples...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00434a071

    authors: Dizdaroglu M,Gajewski E,Reddy P,Margolis SA

    更新日期:1989-04-18 00:00:00

  • Crystal structure and iron-binding properties of the R210K mutant of the N-lobe of human lactoferrin: implications for iron release from transferrins.

    abstract::Lactoferrin (Lf) and serum transferrin (Tf) combine high-affinity iron binding with an ability to release this iron at reduced pH. Lf, however, retains iron to significantly lower pH than Tf, giving the two proteins distinct functional roles. In this paper, we compared the iron-release profiles for human Lf, Tf, and t...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi0001224

    authors: Peterson NA,Anderson BF,Jameson GB,Tweedie JW,Baker EN

    更新日期:2000-06-06 00:00:00

  • Deuterium kinetic isotope effects and the mechanism of the bacterial luciferase reaction.

    abstract::A combined experimental and theoretical investigation of the deuterium isotope effects on the bacterial luciferase reaction is described. The experimental studies focus on determining if the unusual aldehydic deuterium isotope effect of approximately 1.5 observed in these reactions is an intrinsic isotope effect resul...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi972266x

    authors: Francisco WA,Abu-Soud HM,DelMonte AJ,Singleton DA,Baldwin TO,Raushel FM

    更新日期:1998-02-24 00:00:00

  • The stability of chicken nucleoside triphosphate diphosphohydrolase 8 requires both of its transmembrane domains.

    abstract::Chicken nucleoside triphosphate diphosphohydrolase 8 (NTPDase8) is a cell surface ectonucleotidase with a large extracellular domain (ECD) containing the active site and is anchored to the membrane by two transmembrane domains (TMDs) at the N- and C-termini. Unlike other cell surface NTPDases that have been characteri...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi901820c

    authors: Li CS,Lee Y,Knowles AF

    更新日期:2010-01-12 00:00:00

  • Ultraviolet-induced thymine hydrates in DNA are excised by bacterial and human DNA glycosylase activities.

    abstract::Ultraviolet irradiation of DNA results in various pyrimidine modifications. We studied the excision of an ultraviolet thymine photoproduct by Escherichia coli endonuclease III and by a preparation of human WI-38 cells. These enzymes cleave UV-irradiated DNA at apyrimidinic sites formed by glycosylic removal of the pho...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00483a009

    authors: Ganguly T,Weems KM,Duker NJ

    更新日期:1990-08-07 00:00:00

  • Identification of the genes encoding Mn2+-dependent RNase HII and Mg2+-dependent RNase HIII from Bacillus subtilis: classification of RNases H into three families.

    abstract::Database searches indicated that the genome of Bacillus subtilis contains three different genes encoding RNase H homologues. The ypdQ gene encodes an RNase HI homologue with 132 amino acid residues, whereas the rnh and ysgB genes encode RNase HII homologues with 255 and 313 amino acid residues, respectively. RNases HI...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi982207z

    authors: Ohtani N,Haruki M,Morikawa M,Crouch RJ,Itaya M,Kanaya S

    更新日期:1999-01-12 00:00:00

  • The steric gate amino acid tyrosine 112 is required for efficient mismatched-primer extension by human DNA polymerase kappa.

    abstract::Human DNA is continuously damaged by exogenous and endogenous genotoxic insults. To counteract DNA damage and ensure the completion of DNA replication, cells possess specialized DNA polymerases (Pols) that bypass a variety of DNA lesions. Human DNA polymerase kappa (hPolkappa) is a member of the Y-family of DNA Pols a...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi900153t

    authors: Niimi N,Sassa A,Katafuchi A,Grúz P,Fujimoto H,Bonala RR,Johnson F,Ohta T,Nohmi T

    更新日期:2009-05-26 00:00:00

  • SNX-325, a novel calcium antagonist from the spider Segestria florentina.

    abstract::A novel selective calcium channel antagonist peptide, SNX-325, has been isolated from the venom of the spider Segestria florentina. The peptide was isolated using as bioassays the displacement of radioiodinated omega-conopeptide SNX-230 (MVIIC) from rat brain synaptosomal membranes, as well as the inhibition of the ba...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00026a015

    authors: Newcomb R,Palma A,Fox J,Gaur S,Lau K,Chung D,Cong R,Bell JR,Horne B,Nadasdi L

    更新日期:1995-07-04 00:00:00

  • Intersubunit association induces unique allosteric dependence of the T127L CRP mutant on pH.

    abstract::The allosteric activation of the T127-->L mutant of 3',5'-cyclic adenosine monophosphate (cAMP) receptor protein (CRP) by cAMP changes from an exothermic, independent two-site binding mechanism at pH 7.0 to an endothermic, interacting two-site binding mechanism at pH 5.2, similar to that observed for CRP at pH 7.0 and...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi000225m

    authors: Shi Y,Wang S,Schwarz FP

    更新日期:2000-06-20 00:00:00

  • In vitro analysis of carboxyacyl substrate tolerance in the loading and first extension modules of borrelidin polyketide synthase.

    abstract::The borrelidin polyketide synthase (PKS) begins with a carboxylated substrate and, unlike typical decarboxylative loading PKSs, retains the carboxy group in the final product. The specificity and tolerance of incorporation of carboxyacyl substrate into type I PKSs have not been explored. Here, we show that the first e...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi500951c

    authors: Hagen A,Poust S,de Rond T,Yuzawa S,Katz L,Adams PD,Petzold CJ,Keasling JD

    更新日期:2014-09-30 00:00:00

  • Physical behavior of the hydrophobic core of membranes: properties of 1-stearoyl-2-linoleoyl-sn-glycerol.

    abstract::Phospholipids containing a saturated fatty acid in the primary position and an unsaturated fatty acid in the secondary position are a major structural part of biological membranes. The mixed-chain hydrophobic core of the membranes is the diacylglycerol part. To better understand the core properties of membranes we hav...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00051a015

    authors: Di L,Small DM

    更新日期:1995-12-26 00:00:00