De novo design of α,β-didehydrophenylalanine containing peptides: from models to applications.

Abstract:

:The de novo design of peptides and proteins has emerged as an approach for investigating protein structure and function. The success relies heavily on the ability to design relatively short peptides that can adopt stable secondary structures. To this end, substitution with α,β-dehydroamino acids, especially α,β-didehydrophenylalanine (ΔPhe or ΔF) has blossomed in manifold directions, providing a rich diversity of well-defined structural motifs. Introduction of α,β-didehydrophenylalanine induces β-bends in small and 3(10)-helices in longer peptide sequences. Most favorable conformation of ΔF residues are (φ,ψ) ∼(60°, 30°), (-60°, -30°), (-60°, 150°), and (60°, -150°). These features have been exploited in designing helix-turn-helix, helical bundle arrangements, and glycine zipper type super secondary structural motifs. The unusual capability of α,β-didehydrophenylalanine ring to form a variety of multicentered interactions (N-H…O, C-H…O, C-H…π, and N-H…π) suggests its possible exploitation for future de novo design of supramolecular structures. This work has now been extended to the de novo design of peptides with antibiotic, antifibrillization activity, etc. More recently, self-assembling properties of small dehydropeptides have been explored. This review focuses primarily on the structural and functional behavior of α,β-didehydrophenylalanine containing peptides.

journal_name

Biopolymers

journal_title

Biopolymers

authors

Gupta M,Chauhan VS

doi

10.1002/bip.21561

subject

Has Abstract

pub_date

2011-03-01 00:00:00

pages

161-73

issue

3

eissn

0006-3525

issn

1097-0282

journal_volume

95

pub_type

杂志文章,评审
  • Three steps in the thermal unfolding of F-actin: an experimental evidence.

    abstract::The development of differential scanning calorimetry has resulted in an increased interest in studies of the unfolding process in proteins with the aim of identifying domains and interactions with ligands or other proteins. Several of these studies were done with actin and showed that the thermal unfolding of F-actin ...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20567

    authors: Gicquaud CR,Heppell B

    更新日期:2006-11-01 00:00:00

  • Evidence for the 3 10-helical structure of peptides based on antAib, a fluorophoric, anthracene-fused, 1-aminocyclopentane-1-carboxylic acid.

    abstract::Peptides based on 2-amino-2,3-dihydro-1H-cyclopenta[b]anthracene-2-carboxylic acid (antAib), a fluorescent, achiral, alpha-amino acid belonging to the class of C(i) (alpha)-->C(i) (alpha) cyclized, C(alpha,alpha)-disubstituted glycines, combined with L-Ala, up to the hexamer level, were synthesized by solution methods...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20841

    authors: Wright K,Lohier JF,Wakselman M,Mazaleyrat JP,Peggion C,Formaggio F,Toniolo C

    更新日期:2007-01-01 00:00:00

  • Diverse cyclic seed peptides in the Mexican zinnia (Zinnia haageana).

    abstract::A new family of small plant peptides was recently described and found to be widespread throughout the Millereae and Heliantheae tribes of the sunflower family Asteraceae. These peptides originate from the post-translational processing of unusual seed-storage albumin genes, and have been termed PawS-derived peptides (P...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.22901

    authors: Franke B,Jayasena AS,Fisher MF,Swedberg JE,Taylor NL,Mylne JS,Rosengren KJ

    更新日期:2016-11-01 00:00:00

  • Counteraction ability of TMAO toward different denaturing agents.

    abstract::Differential scanning calorimetry measurements performed on RNase A in aqueous binary solutions containing different concentrations of urea, tetramethylurea, guanidinium chloride, and guanidinium thiocyanate, and in aqueous ternary solutions, containing the same denaturants plus 1 M trimethylamine N-oxide, TMAO, demon...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.23104

    authors: Vigorita M,Cozzolino S,Oliva R,Graziano G,Del Vecchio P

    更新日期:2018-08-01 00:00:00

  • Evidence of hemoglobin dissociation.

    abstract::Bovine carbonmonoxy hemoglobin investigated with light scattering studies is found to dissociate from its native tetramer structure into dimers and monomers. The values of the hydrated tetramer radius, RT = 32.1 A, and the fractional dissociation vs pH, have been obtained at different ionic strengths from the autocorr...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360340607

    authors: Lunelli L,Zuliani P,Baldini G

    更新日期:1994-06-01 00:00:00

  • Synthesis and characterization of polyamides containing unnatural amino acids.

    abstract::We describe the synthesis of several polyamides that retain the secondary structure of proteins and contain derivatizable side chains. The derivatizable side chain allows for further reaction of the polymer chain (e.g., chain cross-linking or addition of pendant groups). Polymers of alpha-amino acids containing a term...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360350509

    authors: Guinn RM,Margot AO,Taylor JR,Schumacher M,Clark DS,Blanch HW

    更新日期:1995-05-01 00:00:00

  • Look-up tables for protein solvent accessibility prediction and nearest neighbor effect analysis.

    abstract::We developed dictionaries of two-, three-, and five-residue patterns in proteins and computed the average solvent accessibility of the central residues in their native proteins. These dictionaries serve as a look-up table for making subsequent predictions of solvent accessibility of amino acid residues. We find that p...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20113

    authors: Wang JY,Ahmad S,Gromiha MM,Sarai A

    更新日期:2004-10-15 00:00:00

  • Phosphorylation stabilizes the N-termini of alpha-helices.

    abstract::The role of phosphorylation in stabilizing the N-termini of alpha-helices is examined using computer simulations of model peptides. The models comprise either a phosphorylated or unphosphorylated serine at the helix N-terminus, followed by nine alanines. Monte Carlo/stochastic Dynamics simulations were performed on th...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/(SICI)1097-0282(199903)49:3<225::AID-BIP4>

    authors: Smart JL,McCammon JA

    更新日期:1999-03-01 00:00:00

  • Quantitative characterization of specific genomic promoters using agarose gel electrophoresis.

    abstract::Over the past decade a large number of studies have focused attention on the role of nucleosomes as negative and positive regulators of specific nuclear functions. Due to the lack of an analytical method to determine the higher order conformation of the nucleosomal arrays that encompass specific genetic loci (e.g., pr...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.10322

    authors: Georgel PT,Hansen JC

    更新日期:2003-04-01 00:00:00

  • Functionalization of a protein surface with per-O-methylated β-cyclodextrin.

    abstract::Per-O-methylated β-cyclodextrin (CD) bearing an iodoacetamide group at the 6-position was synthesized to functionalize protein surfaces. Bovine serum albumin (BSA) was quantitatively modified with the CD derivative by the S(N) 2 reaction of iodoacetamide with a cysteine residue (Cys34) on the BSA surface. The resultan...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.21695

    authors: Kitagishi H,Kashiwa K,Kano K

    更新日期:2012-01-01 00:00:00

  • Effect of chain length of HAV-VP3 synthetic peptides on its interaction with biomembrane models.

    abstract::Shorter analogues of a continuous epitope of hepatitis A virus, VP3(110-121) peptide, failed to react with convalescent sera, indicating the importance of the entire peptide in the epitope structure. To better understand the influence of the structural properties of this 12-mer peptide epitope on its biological activi...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/1097-0282(200012)54:7<477::AID-BIP10>3.0.C

    authors: Sospedra P,Muñoz M,García M,Alsina MA,Mestres C,Haro I

    更新日期:2000-12-01 00:00:00

  • Use of Oxyma as pH modulatory agent to be used in the prevention of base-driven side reactions and its effect on 2-chlorotrityl chloride resin.

    abstract::The presence of low pKa N-hydroxylamines is beneficial in peptide chemistry as they reduce some base-mediated side reactions. Here we evaluated the applicability and buffering capacity of Ethyl 2-cyano-2-(hydroxyimino) acetate (Oxyma) in the prevention of aspartimide/piperidide formation and Pro-based overcoupling and...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.21713

    authors: Subirós-Funosas R,El-Faham A,Albericio F

    更新日期:2012-01-01 00:00:00

  • Synchrotron radiation small angle scattering studies of thermal stability of xylanase XYNII from Trichoderma longibrachiatum.

    abstract::Xylanase XYNII from Trichoderma longibrachiatum is a small protein of the molecular weight 21 kDa, belonging to the family 11 of glycosyl hydrolases, which catalyses hydrolysis of xylan. This article reports thermal stability study of xylanase XYN II conformation in the temperature range 15-65 degrees C by the small a...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20605

    authors: Kozak M

    更新日期:2006-12-15 00:00:00

  • An estimate of the nearest neighbor base-pair content of 5S RNA using CD and absorption spectroscopy.

    abstract::We analyzed the CD and uv absorption spectra of 5S RNA from Escherichia coli using the method developed in the preceding paper. The analysis of spectra of 5S RNA at 20 degrees C in 0.1M NaClO4, 2.5 mM Na+ (phosphate), pH 7.0, and 0.5 mM MgSO4 gave 7 +/- 3.6 A.U base pairs, 25 +/- 3.6 G.C base pairs, and 7.5 +/- 3.6 G....

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360310404

    authors: Johnson KH,Gray DM

    更新日期:1991-03-01 00:00:00

  • Development of crosslink-type tag-probe pairs for fluorescent imaging of proteins.

    abstract::Useful methods of protein labeling via functional peptide tags have been developed in the field of proteome and chemical biology. New tag-probe pairs based on leucine zipper peptides for labeling target proteins are described. These consist of an α-helical probe peptide with an environmental-sensitive fluorescent dye ...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.21444

    authors: Nomura W,Mino T,Narumi T,Ohashi N,Masuda A,Hashimoto C,Tsutsumi H,Tamamura H

    更新日期:2010-01-01 00:00:00

  • Conformation-activity relationship of a novel peptide antibiotic: structural characterization of dermaseptin DS 01 in media that mimic the membrane environment.

    abstract::Dermaseptins, small polycationic peptides synthesized by amphibians, exert a lytic action on bacteria, protozoa, yeast, and filamentous fungi at micromolar concentrations, but unlike polylysines, show little hemolytic activity. Dermaseptins S are active only against bacteria and form aggregates at high peptide/lipid r...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20244

    authors: Castiglione-Morelli MA,Cristinziano P,Pepe A,Temussi PA

    更新日期:2005-01-01 00:00:00

  • Structure-function correlation of outer membrane protein porin from Paracoccus denitrificans.

    abstract::Porins from outer membrane of Gram-negative bacteria have a highly stable structure. Our previous studies on porin from Paracoccus denitrificans showed that the outer membrane protein porin is extremely stable toward heat, pH, and chemical denaturants. The major question we have addressed in this paper is whether the ...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20422

    authors: Sukumaran S,Hauser K,Maier E,Benz R,Mäntele W

    更新日期:2006-07-01 00:00:00

  • The sensitivity of conformational free energies of the alanine dipeptide to atomic site charges.

    abstract::Different atomic point charge sets are obtained for the alpha R and C7,eq conformations of the alanine dipeptide by fitting the charges of each conformation to the respective ab initio electrostatic potential surfaces both individually and simultaneously, in both the united atom and the all-atom representations. Using...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/(SICI)1097-0282(199701)41:1<73::AID-BIP7>3

    authors: Resat H,Maye PV,Mezei M

    更新日期:1997-01-01 00:00:00

  • Solvent effect on binding thermodynamics of biopolymers.

    abstract::The indirect solvent-induced effect on the free energy of binding of biopolymers is examined within the framework of classical statistical mechanics. We focus specifically on the role of the solute-solvent hydrogen bonding. In particular, we have estimated the first order solvent effect on the indirect interaction bet...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360290604

    authors: Ben-Naim A,Ting KL,Jernigan RL

    更新日期:1990-05-01 00:00:00

  • A two-dimensional NMR study of exchange behavior of amide hydrogens in a lysozyme derivative with an extra cross-link between Glu35 and Trp108--quenching of cooperative fluctuations and effects on the protein stability.

    abstract::Two-dimensional nmr spectra [correlated spectroscopy (COSY), homonuclear Hartmann-Hahn (HOHAHA), nuclear Overhauser effect spectroscopy (NOESY)] have been observed for cross-linked lysozyme, a chemically modified lysozyme derivative with an extra ester cross-link between residues E35 and W108. Eight shifted cross-peak...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/(SICI)1097-0282(199702)41:2<131::AID-BIP2>

    authors: Noda Y,Fukuda Y,Segawa S

    更新日期:1997-02-01 00:00:00

  • Optical properties of ovalbumin in 0.130-2.50 microm spectral region.

    abstract::In our continuing series of measurements of the complex index of refraction for representative samples of biological materials, we measured ovalbumin (egg albumin) over the spectral region from 0.130 (76,923 cm(-1)) to 2.50 microm (4000 cm(-1)). Films of ovalbumin suitable for optical analyses were prepared and measur...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.1004

    authors: Arakawa ET,Tuminello PS,Khare BN,Milham ME

    更新日期:2001-01-01 00:00:00

  • Studies of DNA dumbbells. VI. Analysis of optical melting curves of dumbbells with a sixteen-base pair duplex stem and end-loops of variable size and sequence.

    abstract::Optical melting curves of 22 DNA dumbbells with the 16-base pair duplex sequence 5'-G-C-A-T-C-A-T-C-G-A-T-G-A-T-G-C-3' linked on both ends by single-strand loops of A, or C, sequences (iota = 2, 3, 4, 6, 8, 10, 14). T sequences (iota = 2, 3, 4, 6, 8, 10), and G iota sequences (iota = 2, 4) were measured in phosphate b...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/(SICI)1097-0282(199612)39:6%3C779::AID-BIP

    authors: Paner TM,Riccelli PV,Owczarzy R,Benight AS

    更新日期:1996-12-01 00:00:00

  • Fast membrane association is a crucial factor in the peptide pep-1 translocation mechanism: a kinetic study followed by surface plasmon resonance.

    abstract::The use of peptide carriers, termed "cell-penetrating peptides (CPPs)" has attracted much attention due to their potential for cellular delivery of hydrophilic molecules with pharmacological interest, overcoming the membrane barrier. These peptides are able to deliver attached cargos in a nontoxic manner, with the upt...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.21367

    authors: Henriques ST,Castanho MA,Pattenden LK,Aguilar MI

    更新日期:2010-01-01 00:00:00

  • Quantitative IR spectrophotometry of peptide compounds in water (H2O) solutions. I. Spectral parameters of amino acid residue absorption bands.

    abstract::Infrared spectra of the amino acid residues in H2O solution have been obtained in the 1800-1400-cm-1 region. It has been established that amino acid residues of arginine, asparagine, glutamine, aspartic and glutamic acids, lysine, tyrosine, histidine, and phenylalanine have intensive absorption in this spectral region...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360301309

    authors: Venyaminov SYu,Kalnin NN

    更新日期:1990-01-01 00:00:00

  • Molecular and biological constraints on ligand-binding affinity and specificity.

    abstract::Interactions between biological macromolecules have characteristic values of affinity and specificity that are set according to the biological function that is served by the interaction in the organism. Here we examine the molecular mechanisms that are used to achieve the required values of affinity and specificity in...

    journal_title:Biopolymers

    pub_type: 杂志文章,评审

    doi:10.1002/(SICI)1097-0282(1997)44:2<181::AID-BIP5>3.

    authors: Szwajkajzer D,Carey J

    更新日期:1997-01-01 00:00:00

  • The amplitude of local angular motion of purines in DNA in solution.

    abstract::Nuclear magnetic resonance and optical experiments are combined to determine the rms amplitude of local angular motion of purines in DNA in solution. A 12 base-pair duplex DNA with the sequence d(CGCGAATTCGCG)2 is deuterated at the H8 positions of adenine and guanine by exchange with solvent at 55 degrees C. The deute...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360340404

    authors: Nuutero S,Fujimoto BS,Flynn PF,Reid BR,Ribeiro NS,Schurr JM

    更新日期:1994-04-01 00:00:00

  • Multinuclear NMR and FTIR studies of new polyoxaalkyl esters of lasalocid and their complexes with lithium and sodium cations.

    abstract::Three new polyoxaalkyl esters of lasalocid are synthesized. Their ability to form complexes with Li(+) and Na(+) cations is studied using multinuclear NMR methods, FTIR spectroscopy in the middle and far IR regions, and mass spectrometry. It is found that lasalocid esters form only 1:1 complexes with the metal cations...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.10194

    authors: Pankiewicz R,Schroeder G,Gierczyk B,Brzezinski B,Bartl F

    更新日期:2002-10-15 00:00:00

  • Structure-based design of novel nonpeptide inhibitors of the Src SH2 domain:phosphotyrosine mimetics exploiting multifunctional group replacement chemistry.

    abstract::A series of novel nonpeptide inhibitors of the pp60(c-Src) (Src) SH2 domain is described that exploit multifunctional group replacement of the phenylphosphate moiety of phosphotyrosine (pTyr). Relative to an x-ray structure of citrate complexed to the pTyr binding site of the Src SH2 domain, these nonpeptide ligands i...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.10600

    authors: Sundaramoorthi R,Kawahata N,Yang MG,Shakespeare WC,Metcalf CA 3rd,Wang Y,Merry T,Eyermann CJ,Bohacek RS,Narula S,Dalgarno DC,Sawyer TK

    更新日期:2003-01-01 00:00:00

  • Influence of structure of human, rat, and bovine serum albumins on binding properties of photoactive drug hypericin.

    abstract::Fluorescence binding measurements and molecular modeling were employed to study the interaction of hypericin (Hyp) with human (HSA), rat (RSA), and bovine (BSA) serum albumins. Fluorescence emission data show the solubility of Hyp increasing in the order BSA, HSA, and RSA. Molecular modeling was used to construct the ...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.10110

    authors: Hritz J,Kascakova S,Ulicny J,Miskovsky P

    更新日期:2002-01-01 00:00:00

  • PEGylated PAMAM dendrimers loading oxaliplatin with prolonged release and high payload without burst effect.

    abstract::Oxaliplatin (OXA) was coupled to PEGylated polyamidoamine dendrimers of fourth generation (G4-PEG@OXA) in the comparison to PEGylated ones of odd generation (G3.5-PEG@OXA). Proton nuclear magnetic resonance and Fourier-transform infrared spectroscopy were used to confirm the successful incorporation of OXA as well as ...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.23272

    authors: Ho MN,Bach LG,Nguyen DH,Nguyen CH,Nguyen CK,Tran NQ,Nguyen NV,Hoang Thi TT

    更新日期:2019-07-01 00:00:00