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A survey of literature for the various types of helices experimentally observed in high-resolution single crystal x-ray diffraction analyses of peptides has allowed to determine accurate conformational and helical parameters for the various secondary structures such as the alpha-helix, the 3(10)-helix, the fully extended conformation (2(5)-helix) and the beta-bend ribbon spiral. For each of these structures the characteristic phi, psi conformational parameters, n, the number of residues per turn, h, the height per residues and p, the pitch of the helix are described. 相似文献
3.
Vittorio Moretto Fernando Formaggio Marco Crisma Gian Maria Bonora Claudio Toniolo Ettore Benedetti Antonello Santini Michele Saviano Benedetto Di Blasio Carlo Pedone 《Journal of peptide science》1996,2(1):14-27
A complete series of terminally blocked, monodispersed homo-oligopeptides (to the pentamer level) from the sterically demanding, medium-ring alicyclic Cα,α-disubstituted glycine 1-aminocyclooctane-1-carb oxylic acid (Ac8c), and two Ala/Ac8c tripeptides, were synthesized by solution methods and fully characterized. The preferred conformation of all the oligopeptides was determined in deuterochloroform solution by IR absorption and 1H-NMR. The molecular structures of the amino acid derivative Z-Ac8c-OH, the dipeptide pBrBz- (Ac8c)2-OH and the tripeptide pBrBz-(Ac8c)3-OtBu were assessed in the crystal state by X-ray diffraction. Conformational energy computations were performed on the monopeptide Ac-Ac8c-NHMe. Taken together, the results obtained strongly support the view that the Ac8c residue is an effective β-turn and helix former. A comparison is also made with the conformational preferences of α-aminoisobutyric acid, the prototype of Cα, α-disubstituted glycines, and of the other members of the family of 1-aminocycloalkane-1-carboxylic acids (Acnc, with n=3, 5–7) investigated so far. The implications for the use of the Ac8c residue in peptide conformational design are considered. 相似文献
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Milov AD Samoilova MI Tsvetkov YD Jost M Peggion C Formaggio F Crisma M Toniolo C Handgraaf JW Raap J 《化学与生物多样性》2007,4(6):1275-1298
Three analogs of alamethicin F50/5, labelled with the TOAC (='2,2,6,6-tetramethylpiperidin-1-oxyl-4-amino-4-carboxylic acid') spin label at positions 1 (Alm1), 8 (Alm8), and 16 (Alm16), resp., were studied by Electron-Spin-Resonance (ESR) and Pulsed Electron-Electron Double-Resonance (PELDOR) techniques in solvents of different polarity to investigate the self-assembly of amphipathic helical peptides in membrane-mimicking environments. In polar solvents, alamethicin forms homogeneous solutions. In the weakly polar chloroform/toluene 1 : 1 mixture, however, this peptide forms aggregates that are detectable at 293 K by ESR in liquid solution, as well as by PELDOR in frozen, glassy solution at 77 K. In liquid solution, free alamethicin molecules and their aggregates show rotational-mobility correlation times tau(r) of 0.87 and 5.9 ns, resp. Based on these values and analysis of dipole-dipole interactions of the TOAC labels in the aggregates, as determined by PELDOR, the average number N of alamethicin molecules in the aggregates is estimated to be less than nine. A distance-distribution function between spin labels in the supramolecular aggregate was obtained. This function exhibits two maxima: a broad one at a distance of 3.0 nm, and a wide one at a distance of ca. 7 nm. A molecular-dynamics (MD)-based model of the aggregate, consisting of two parallel tetramers, each composed of four molecules arranged in a 'head-to-tail' fashion, is proposed, accounting for the observed distances and their distribution. 相似文献
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The preferred conformations of peptides heavily based on the currently extensively exploited achiral and chiral alpha-amino acids with a quaternary alpha-carbon atom, as determined by conformational energy computations, crystal-state (x-ray diffraction) analyses, and solution ((1)H-NMR and spectroscopic) investigations, are reviewed. It is concluded that 3(10)/alpha-helical structures and the fully extended (C(5)) conformation are preferentially adopted by peptide sequences characterized by this family of amino acids, depending upon overall bulkiness and nature (e.g., whether acyclic or C(alpha) (i) <--> C(alpha) (i) cyclized) of their side chains. The intriguing relationship between alpha-carbon chirality and bend/helix handedness is also illustrated. gamma-Bends and semiextended conformations are rarely observed. Formation of beta-sheet structures is prevented. 相似文献
6.
Formaggio F Peggion C Crisma M Kaptein B Broxterman QB Mazaleyrat JP Wakselman M Toniolo C 《Chirality》2004,16(6):388-397
Recent applications in our laboratories of electronic circular dichroism to the study of peptide secondary structures and their changes under external stimuli are briefly reviewed. More specifically, this article deals with: 1). characterization of a novel peptide conformation; 2). origin of amino acid homo-chirality on Earth; 3). bend and helical peptides as spacers; and 4). transfer and propagation of chirality in peptides. 相似文献
7.
As an additional step toward the dissection of the factors responsible for the onset of 3(10)-helix vs alpha-helix in peptides, in this paper we describe the results of a three-dimensional (3D) structural analysis by x-ray diffraction of the N(alpha)-acylated heptapeptide alkylamide mBrBz-L-Iva-L-(alphaMe)Val-L-Abu-L-(alphaMe)Val-L-(alphaMe)Phe-L-(alphaMe)Val-L-Iva-NHMe characterized by a single (L-Abu3) C(alpha)-trisubstituted and six C(alpha)-tetrasubstituted alpha-amino acids. We find that in the crystal state this peptide is folded in a mixed helical structure with short elements of 3(10)-helix at either terminus and a central region of alpha-helix. This finding, taken together with the published NMR and x-ray diffraction data on the all C(alpha)-methylated parent sequence and its L-Val2 analog (also the latter heptapeptide has a single C(alpha)-trisubstituted alpha-amino acid) strongly supports the view that one C(alpha)-trisubstituted alpha-amino acid inserted near the N-terminus of an N(alpha)-acylated heptapeptide alkylamide sequence may be enough to switch a regular 3(10)-helix into an essentially alpha-helical conformation. As a corollary of this work, the x-ray diffraction structure of the N(alpha)-protected, C-terminal tetrapeptide alkylamide Z-L-(alphaMe)Val-L-(alphaMe)Phe-L-(alphaMe)Val-L-Iva-NHMe, also reported here, is clearly indicative of the preference of this fully C(alpha)-methylated, short peptide for the 3(10)-helix. As the same terminally blocked sequence is mixed 3(10)/alpha-helical in the L-Abu3 heptapeptide amide but regular 3(10)-helical in the tetrapeptide amide and in the parent heptapeptide amide, these results point to an evident plasticity even of a fully C(alpha)-methylated short peptide. 相似文献
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Eric Mossel Fernando Formaggio Giovanni Valle Marco Crisma Claudio Toniolo Mitsunobu Doi Toshimasa Ishida Quirinus B. Broxterman Johan Kamphuis 《Letters in Peptide Science》1998,5(2-3):223-225
In order to obtain further information on the role played by phenyl ring position in the C-methylated -amino acid side chain on peptide preferred conformation, the crystal-state structural preferences of C-methyl, C-phenylglycine peptides have been determined by X-ray diffraction. This study shows that either the fully extended conformation or the -bend/310-helical structures are adopted by peptides characterized by this C-methylated, -branched, aromatic -amino acid. 相似文献
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Marina Gobbo Laura Biondi Fernando Filira Fernando Formaggio Marco Crisma Raniero Rocchi Claudio Toniolo Quirinus B. Broxterman Johan Kamphuis 《International journal of peptide research and therapeutics》1998,5(2-3):105-107
Summary A series of longer analogues of the C-peptide of RNAse A has been synthesized with the aim of assessing the helix induction
potential in water of α-methyl, α-amino acids at the N-terminus of the chain. The circular dichroism data indicate that one
isovaline residue is effective in increasing the helix content of the 13-residue peptide by about 7%. 相似文献
10.
Mossel Eric Formaggio Fernando Crisma Marco Toniolo Claudio Sonke Theo Roos Eric C. Broxterman Quirinus B. Kamphuis Johan 《International journal of peptide research and therapeutics》1998,5(1):43-48
Summary Reaction of the N-carboxyanhydride from Cα-methyld-phenylglycine with either 6-aminopenicillanic acid or 7-amino-3-desacetoxy-cephalosporanic acid furnishes the corresponding
ampicillin and cephalexin analogues. Neither the biological activity nor the chemical stability of these new semi-synthetic
antibiotics are superior to those of their unmethylated counterparts. 相似文献