Solid-state conformations of aminosuccinyl peptides: crystal structure of tert-butyloxycarbonyl-L-leucyl-L-aminosuccinyl-L-phenylalaninami de.

Abstract:

:The protected tripeptide tert-butyloxycarbonyl-L-leucyl-L-aminosuccinyl-L-phenylalaninamide crystallizes in the orthorhombic space group P2(1)2(1)2(1), with a = 6.214(3), b = 12.832(3), c = 33.094(4) A, Z = 4. The structure was solved by direct methods using MULTAN 80 and refined to an R value of 0.055 for 1458 reflections. The bond lengths and angles are in good agreement with the standard values. The peptide backbone adopts a type II' beta-bend conformation with a weak intramolecular hydrogen bond between the CO group of the leucyl residue and the C-terminal NH2 group. In agreement with previous studies, this structure confirms the high propensity of aminosuccinyl peptides to adopt a type II' beta-bend conformation. The role of this conformation in relation to the deamidation process in proteins is also discussed.

journal_name

Biopolymers

journal_title

Biopolymers

authors

Capasso S,Mazzarella L,Sica F,Zagari A

doi

10.1002/bip.360280116

subject

Has Abstract

pub_date

1989-01-01 00:00:00

pages

139-47

issue

1

eissn

0006-3525

issn

1097-0282

journal_volume

28

pub_type

杂志文章
  • Peptide antagonists of the calcitonin gene-related peptide (CGRP) receptor with improved pharmacokinetics and pharmacodynamics.

    abstract::Antagonism of the calcitonin gene-related peptide (CGRP) receptor may be a useful approach for migraine treatment. Selective PEGylated peptide antagonists to the CGRP receptor are described, derived from CGRP(8-37) with polymer derivatization at an engineered lysine-25 residue. Potent PEGylated peptides with improved ...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.22270

    authors: Miranda LP,Shi L,Holder JR,Wright M,Gegg CV,Johnson E,Wild K,Stenkilsson M,Doellgast G,Manning BH,Salyers K

    更新日期:2013-07-01 00:00:00

  • Molecular dynamic simulation studies on the effect of one residue chain staggering on the structure and stability of heterotrimeric collagen-like peptides with interruption.

    abstract::A systematic molecular dynamics (MD) simulation has been carried out on collagen-like peptides with different combinations of interruptions in the Gly-X(AA) -Y(AA) repeats. Although experimental studies have been carried out to elucidate the structural consequences of homotrimeric collagen-like peptides, this is the f...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.22085

    authors: Singam ER,Balamurugan K,Gopalakrishnan R,Subramanian SR,Subramanian V,Ramasami T

    更新日期:2012-11-01 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

  • Thermal stability of DNA with interstrand crosslinks.

    abstract::Although many anticancer drugs exert their biological activity by forming DNA interstrand crosslinks (ICLs), the thermodynamics of biologically relevant long crosslinked DNAs has not been intensively studied in contrast to short duplexes. Here, we carry out computer modeling of the shift of melting temperature of long...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.22077

    authors: Chang CL,Lando DY,Fridman AS,Hu CK

    更新日期:2012-10-01 00:00:00

  • Molecular mass and chain conformation of carboxymethylated derivatives of beta-glucan from sclerotia of Pleurotus tuber-regium.

    abstract::Seven water-insoluble (1 --> 3)-beta-D-glucan fractions TM8-1 to TM8-7 with weight-average molecular mass M(w) ranged from 2.22 to 77.4 x 10(4) obtained from the sclerotia of Pleurotus tuber-regium were carboxymethylated to produce the water-soluble fractions CTM8-1 to CTM8-7 with M(w) ranged from 3.87 to 87.8 x 10(4)...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.10277

    authors: Zhang M,Zhang L,Cheung PC

    更新日期:2003-02-01 00:00:00

  • RNA solvation: a molecular dynamics simulation perspective.

    abstract::With the availability of accurate methods to treat the electrostatic long-range interactions, molecular dynamics simulations have resulted in refined dynamical models of the structure of the hydration shell around RNA motifs. The models reviewed here range from basic Watson-Crick to more specific noncanonical base pai...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/1097-0282(2000)56:4<266::AID-BIP10027>3.0.

    authors: Auffinger P,Westhof E

    更新日期:2000-01-01 00:00:00

  • Fourier transform IR spectroscopy study for new insights into molecular properties and activation mechanisms of visual pigment rhodopsin.

    abstract::Fourier transform IR (FTIR) spectroscopy has been successfully applied in recent years to examine the functional and structural properties of the membrane protein rhodopsin, a prototype G protein coupled receptor. Unlike UV-visible spectroscopy, FTIR spectroscopy is structurally sensitive. It may give us both global i...

    journal_title:Biopolymers

    pub_type: 杂志文章,评审

    doi:10.1002/bip.10407

    authors: Vogel R,Siebert F

    更新日期:2003-01-01 00:00:00

  • Vibrational studies of the disulfide group in proteins. VI. General correlations of SS and CS stretch frequencies with disulfide bridge geometry.

    abstract::Normal mode calculations have been done on a range of disulfide bridge conformations in order to determine how the SS stretch and CS stretch frequencies depend on structure. In addition to varying the C alpha C beta SS and NC alpha C beta S dihedral angles, we have varied the phi, psi of the adjoining peptide groups s...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360320813

    authors: Qian W,Krimm S

    更新日期:1992-08-01 00:00:00

  • Total chemical synthesis and oxidative folding of delta-conotoxin PVIA containing an N-terminal propeptide.

    abstract::Small disulfide-rich peptides are translated as larger precursors typically containing an N-terminal prepro sequence. In this study, we investigated the role of a propeptide in the oxidative folding of an extremely hydrophobic delta-conotoxin, PVIA. delta-Conotoxin PVIA (delta-PVIA) is a 29-amino acid neurotoxin stabi...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20211

    authors: Buczek P,Buczek O,Bulaj G

    更新日期:2005-01-01 00:00:00

  • The role of proline-containing peptide triads in β-sheet formation: A kinetic study.

    abstract::The design of biomimetic materials through molecular self-assembly is a growing area of modern nanotechnology. With problems of protein folding, self-assembly, and sequence-structure relationships as essential in nanotechnology as in biology, the effect of the nucleation of β-hairpin formation by proline on the foldin...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.22622

    authors: Takor GA,Higashiya S,Sikirzhytski VK,Seeley JP,Lednev IK,Welch JT

    更新日期:2015-06-01 00:00:00

  • A differential scanning calorimetric study of the conformational transitions of schizophyllan in mixtures of water and dimethylsulfoxide.

    abstract::The thermal conformational transitions of two sonicated samples of schizophyllan were studied in water-dimethylsulfoxide (DMSO) mixtures by high-sensitivity differential scanning calorimetry (DSC). Two transitions were observed over most of the range of solvent compositions. These were assigned to an internal change o...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360280208

    authors: Kitamura S,Kuge T

    更新日期:1989-02-01 00:00:00

  • Peptide structural analysis by solid-state NMR spectroscopy.

    abstract::Solid-state nmr spectroscopy provides a robust method for investigating polypeptides that have been prepared by chemical synthesis and that are immobilized by strong interactions with solid surfaces or large macroscopic complexes. Solid-state nmr spectroscopy has been widely used to investigate membrane polypeptides o...

    journal_title:Biopolymers

    pub_type: 杂志文章,评审

    doi:10.1002/(SICI)1097-0282(1999)51:3<174::AID-BIP2>3.

    authors: Bechinger B,Kinder R,Helmle M,Vogt TC,Harzer U,Schinzel S

    更新日期:1999-01-01 00:00:00

  • Spectroscopic studies of interaction of chlorobenzylidine with DNA.

    abstract::Electronic absorbance and fluorescence titrations are used to probe the interaction of chlorobenzylidine with DNA. The binding of chlorobenzylidine to DNA results in hypochromism, a small shift to a longer wavelength in the absorption spectra, and emission quenching in the fluorescence spectra. These spectral characte...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.10001

    authors: Zhong W,Yu JS,Huang W,Ni K,Liang Y

    更新日期:2001-01-01 00:00:00

  • Impact of thymine glycol damage on DNA duplex energetics: Correlations with lesion-induced biochemical and structural consequences.

    abstract::The magnitude and nature of lesion-induced energetic perturbations empirically correlate with mutagenicity/cytotoxicity profiles and can be predictive of lesion outcomes during polymerase-mediated replication in vitro. In this study, we assess the sequence and counterbase-dependent energetic impact of the Thymine glyc...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.22680

    authors: Minetti CA,Remeta DP,Iden CR,Johnson F,Grollman AP,Breslauer KJ

    更新日期:2015-09-01 00:00:00

  • 13C CPMAS NMR studies of the elastin-like polypeptide (LGGVG)n.

    abstract::The elucidation of structure-function relationships in insoluble elastin is often approached using elastin-like polypeptides. In this manner, the characterization of the different regions in this extensive biopolymer may be facilitated in a "piece-wise" manner. Our solid-state NMR experiments indicate that (LGGVG)n ha...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.10470

    authors: Kumashiro KK,Kurano TL,Niemczura WP,Martino M,Tamburro AM

    更新日期:2003-10-01 00:00:00

  • Molecular design and genetic optimization of antimicrobial peptides containing unnatural amino acids against antibiotic-resistant bacterial infections.

    abstract::Antimicrobial peptides (AMPs) have been the focus of intense research towards the finding of a viable alternative to current small-molecule antibiotics, owing to their commonly observed and naturally occurring resistance against pathogens. However, natural peptides have many problems such as low bioavailability and hi...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.22885

    authors: He Y,He X

    更新日期:2016-09-01 00:00:00

  • Vibrations-determined properties of green fluorescent protein.

    abstract::The physicochemical characteristics of the green fluorescent protein (GFP), including the thermodynamic properties (entropy, enthalpy, Gibbs' free energy, heat capacity), normal mode vibrations, and atomic fluctuations, were investigated. The Gaussian 03 computational chemistry program was employed for normal mode ana...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20264

    authors: Krasnenko V,Tkaczyk AH,Tkaczyk ER,Farkas O,Mauring K

    更新日期:2005-06-15 00:00:00

  • Cyclotide synthesis and supply: from plant to bioprocess.

    abstract::Cyclotides are disulfide-rich miniproteins with a circular backbone and a knotted arrangement ofdisulfide bonds. Because these plant-derived peptides are resistant to degradation and exhibit a diverse range of bioactivity they have become important agronomic and industrial objectives. They belong to a group of compoun...

    journal_title:Biopolymers

    pub_type: 杂志文章,评审

    doi:10.1002/bip.21466

    authors: Dörnenburg H

    更新日期:2010-01-01 00:00:00

  • Keratin-lipid structural organization in the corneous layer of snake.

    abstract::The shed epidermis (molt) of snakes comprises four distinct layers. The upper two layers, here considered as beta-layer, contain essentially beta-keratin. The following layer, known as mesos-layer, is similar to the human stratum corneum, and is formed by thin cells surrounded by intercellular lipids. The latter layer...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.21184

    authors: Ripamonti A,Alibardi L,Falini G,Fermani S,Gazzano M

    更新日期:2009-12-01 00:00:00

  • Exploration of the conformational space of oxytocin and arginine-vasopressin using the electrostatically driven Monte Carlo and molecular dynamics methods.

    abstract::Conformational analysis of the neurohypophyseal hormones oxytocin (OT) and arginine-vasopressin (AVP) has been carried out using two different computational approaches and three force fields, namely by the Electrostatically Driven Monte Carlo (EDMC) method, with the Empirical Conformational Energy Program for Peptides...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/(sici)1097-0282(199602)38:2<157::aid-bip3>

    authors: Liwo A,Tempczyk A,Ołdziej S,Shenderovich MD,Hruby VJ,Talluri S,Ciarkowski J,Kasprzykowski F,Lankiewicz L,Grzonka Z

    更新日期:1996-02-01 00:00:00

  • Synthetic immunogens. Part IV: Conformational studies on gastrin conjugates with the human immunoglobulin G1 hinge peptide 225-232/225'-232'.

    abstract::Hybrids of the double-chain bis-cystinyl fragment 225-232/225'-232' of human immunoglobulin G1 (IgG1) with the human little-gastrin sequence 2-17 were found to induce in animals a strong antigastrin humoral immune response with antibody titers comparable to those raised with conventional gastrin/carrier-protein conjug...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360310603

    authors: Moroder L,Bali JP,Kobayashi Y

    更新日期:1991-05-01 00:00:00

  • Transfer RNA recognition by aminoacyl-tRNA synthetases.

    abstract::The aminoacyl-tRNA synthetases are an ancient group of enzymes that catalyze the covalent attachment of an amino acid to its cognate transfer RNA. The question of specificity, that is, how each synthetase selects the correct individual or isoacceptor set of tRNAs for each amino acid, has been referred to as the second...

    journal_title:Biopolymers

    pub_type: 杂志文章,评审

    doi:10.1002/(SICI)1097-0282(1999)52:1<1::AID-BIP1>3.0.

    authors: Beuning PJ,Musier-Forsyth K

    更新日期:1999-01-01 00:00:00

  • New directions for protease inhibitors directed drug discovery.

    abstract::Proteases play crucial roles in various biological processes, and their activities are essential for all living organisms-from viruses to humans. Since their functions are closely associated with many pathogenic mechanisms, their inhibitors or activators are important molecular targets for developing treatments for va...

    journal_title:Biopolymers

    pub_type: 杂志文章,评审

    doi:10.1002/bip.22780

    authors: Hamada Y,Kiso Y

    更新日期:2016-11-04 00:00:00

  • A quantum-dynamics study of the prototropic tautomerism of guanine and its contribution to spontaneous point mutations in Escherichia coli.

    abstract::High-level quantum-chemical and quantum-dynamics calculations are reported on the tautomerization equilibrium and rate constants of guanine and its complexes with one and two water molecules. The results are used to estimate the fraction of guanine present in the cell during DNA synthesis as the unwanted tautomer that...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/1097-0282(2001)61:1<77::AID-BIP10062>3.0.C

    authors: Gorb L,Podolyan Y,Leszczynski J,Siebrand W,Fernández-Ramos A,Smedarchina Z

    更新日期:2001-01-01 00:00:00

  • Interaction between the movement protein of barley yellow dwarf virus and the cell nuclear envelope: role of a putative amphiphilic alpha-helix at the N-terminus of the movement protein.

    abstract::The open reading frame 4 (ORF 4) gene product of barley yellow dwarf virus (BYDV) may act as a movement protein (MP) by assisting the transport of viral genomic RNA across the nuclear envelope (NE) of host plant cells. To investigate interactions between BYDV MP and the NE, wild-type and mutant open reading frame (ORF...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20334

    authors: Liu K,Xia Z,Zhang Y,Wen Y,Wang D,Brandenburg K,Harris F,Phoenix DA

    更新日期:2005-10-05 00:00:00

  • Morphology and aggregation of RADA-16-I peptide Studied by AFM, NMR and molecular dynamics simulations.

    abstract::RADA-16-I is a self-assembling peptide which forms biocompatible fibrils and hydrogels. We used molecular dynamics simulations, atomic-force microscopy, NMR spectroscopy, and thioflavin T binding assay to examine size, structure, and morphology of RADA-16-I aggregates. We used the native form of RADA-16-I (H-(ArgAlaAs...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.22755

    authors: Bagrov D,Gazizova Y,Podgorsky V,Udovichenko I,Danilkovich A,Prusakov K,Klinov D

    更新日期:2016-01-01 00:00:00

  • Beta-hairpin stabilization in a 28-residue peptide derived from the beta-subunit sequence of human chorionic gonadotropin hormone.

    abstract::The beta-subunit of the human chorionic gonadotropin (hCG) hormone, which is believed to be related to certain types of cancer, contains three hairpin-like fragments. To investigate the role of beta-hairpin formation in the early stages of the hCGbeta folding, a 28-residue peptide with the sequence RDVRFESIRLPGSPRGVNP...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/(SICI)1097-0282(19991005)50:4<413::AID-BIP

    authors: Silva RA,Sherman SA,Keiderling TA

    更新日期:1999-10-05 00:00:00

  • Secondary structure of a core protein from pig skin proteodermatan sulfate: CD and Fourier transform IR spectroscopic studies in solution.

    abstract::The secondary structure of a 38 kDa core protein from pig skin proteodermatan sulfate (PDS), was investigated in solution using CD and Fourier transform (FT) ir spectroscopy. Both techniques generally have provided complementary data on the secondary structures of proteins. CD spectral analysis has shown that the core...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360281109

    authors: Renugopalakrishnan V,Damle SP,Horowitz PM,Moore S,Hutson TB,Gregory JD

    更新日期:1989-11-01 00:00:00

  • Synthesis of new hydrophilic microspheres: optimized carriers for microparticle-enhanced nephelometric immunoassays.

    abstract::To optimize antigen-antibody reactions, we have synthesized chemically well-defined hydrophilic microspheres. Proteins or haptens were covalently linked to these carriers. When the microsphere conjugates were agglutinated by the corresponding antiserum, the size of the complex artificially increased during the immunol...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360320808

    authors: Marchand J,Varcin P,Riochet D,Montagne P,Cuilliere ML,Duheille J,Pau B

    更新日期:1992-08-01 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