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Journal of Peptide Science: An Official Publication of the European Peptide Society

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https://www.readbyqxmd.com/read/28627122/a-biotinylated-peptide-bp21-as-a-novel-potent-anti-anaphylactic-agent-targeting-platelet-activating-factor
#1
Akira Sato, Keiichi Ebina
Platelet-activating factor (PAF) is an important mediator of anaphylaxis and is therefore an anti-anaphylactic drug target. We recently reported that synthetic N-terminally biotinylated peptides (BP4-BP29) inhibit PAF by directly interacting with PAF and its metabolite/precursor lyso-PAF. In this study, we investigated whether the biotinylated peptides can inhibit anaphylactic reactions in vivo. In mouse models of anaphylaxis, one of the peptides, BP21, markedly and dose-dependently inhibited hypothermia with a maximum dose-response within 30 min after administration, even at doses 20 times lesser than doses of the known PAF antagonist CV-3988...
June 19, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28626916/unexpected-functions-of-angiotensin-converting-enzyme-beyond-its-enzymatic-activity
#2
REVIEW
Jean Martinez
Angiotensin converting enzyme (ACE) is a well-known enzyme, largely studied for its action on hypertension, as it produces angiotensin II from angiotensin I. This paper describes two original behaviours of ACE. We showed that ACE could hydrolyse gastrin, a neuropeptide from the gastrointestinal tract, releasing the C-terminal amidated dipeptide H-Asp-Phe-NH2 . This dipeptide is believed to be involved in the gastrin-induced acid secretion in the stomach. This hypothetic mechanism of action of gastrin resulted in a strategy to rationally design gastrin receptor antagonists...
June 19, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28626925/stoichiometric-analysis-of-oligomeric-states-of-three-class-a-gpcrs-chemokine-cxcr4-dopamine-d2-and-prostaglandin-ep1-receptors-on-living-cells
#3
Kenichi Kawano, Tetsuya Yagi, Nozomu Fukada, Yoshiaki Yano, Katsumi Matsuzaki
G-protein-coupled receptors (GPCRs) form the largest family of transmembrane receptors, and their oligomerization has been suggested to be related to their functions. Despite extensive studies, their oligomeric states are highly controversial. One of the reasons is the overestimation of oligomerization by conventional methods. We recently established a stoichiometric analysis method for precisely determining the oligomeric state of membrane proteins on living cells with the combined use of the coiled-coil labeling method and a spectral imaging technique and showed that the prototypical class-A GPCR β2 -adrenergic receptor (β2 AR) did not form functional oligomers...
June 18, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28612448/visible-light-photoredox-catalyzed-desulfurization-of-thiol-and-disulfide-containing-amino-acids-and-small-peptides
#4
Myungmo Lee, Saskia Neukirchen, Chiara Cabrele, Oliver Reiser
A scalable protocol for the desulfurization of cysteine by using visible light, the photocatalyst Ir(dF(CF3 )ppy)2 (dtb-bpy)PF6 and triethylphosphite under biphasic reaction conditions has been developed. The loading of the catalyst can be as low as 0.01 mol%, which can be efficiently removed during the workup (≤0.3 ppm), giving rise to the corresponding desulfurized product in high yields. This method has been applied also to cystine, penicillamine, and reduced and oxidized glutathione. The desulfurization has been found to be pH sensitive, with an optimal pH value of 6...
June 14, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28608418/characterization-of-an-insulinotropic-peptide-from-skin-secretions-of-odorrana-andersonii
#5
Weijie Shang, Xinwang Yang, Xiaoman Ju, Yueying Xie, Yun Zhang, Wen-Hui Lee
Insulinotropic peptide agents are regarded as potential candidates for anti-diabetic treatment. In the present study, a novel insulinotropic peptide, termed OA-A1, was purified from frog skin secretions of Odorrana andersonii. Mature OA-A1 was determined to be a 1965.049 Da peptide with an amino acid sequence of LVGKLLKGAVGDVCGLLPIC, in which an intramolecular disulfide bridge was formed by two cysteine residues. At the cellular level, OA-A1 exhibited potent proliferation promoting effects on mouse-derived pancreatic β-TC-6 cells and significantly stimulated insulin release in β-TC-6 cells at a minimum concentration of 1 nM...
June 13, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28608410/pyrazole-amino-acids-hydrogen-bonding-directed-conformations-of-3-amino-1h-pyrazole-5-carboxylic-acid-residue
#6
Anna Kusakiewicz-Dawid, Monika Porada, Wioletta Ochędzan-Siodłak, Małgorzata A Broda, Maciej Bujak, Dawid Siodłak
A series of model compounds containing 3-amino-1H-pyrazole-5-carboxylic acid residue with N-terminal amide/urethane and C-terminal amide/hydrazide/ester groups were investigated by using NMR, Fourier transform infrared, and single-crystal X-ray diffraction methods, additionally supported by theoretical calculations. The studies demonstrate that the most preferred is the extended conformation with torsion angles ϕ and ψ close to ±180°. The studied 1H-pyrazole with N-terminal amide/urethane and C-terminal amide/hydrazide groups solely adopts this energetically favored conformation confirming rigidity of that structural motif...
June 13, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28585417/cyanobacterial-peptides-as-a-prototype-for-the-design-of-cathepsin-d-inhibitors
#7
Hao Xu, Keting Bao, Shuai Tang, Jing Ai, Haiyan Hu, Wei Zhang
Cathepsin D (Cath D) is overexpressed and secreted in a number of solid tumors and involved in the progress of tumor invasion, proliferation, metastasis, and apoptosis. Inhibition of Cath D is regarded as an attractive pathway for the development of novel anticancer drugs. Our previous studies revealed that tasiamide B, a cyanobacterial peptide that contained a statine-like unit, exhibited good inhibition against Cath D and other aspartic proteases. Using this natural product as prototype, we designed and synthesized three new analogs, which bear isophthalic acid fragment at the N-terminus and isobutyl amine (1), cyclopropyl amine (2), or 3-methoxybenzyl amine (3) moiety at the C-terminus...
June 6, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28580755/crabrolin-a-natural-antimicrobial-peptide-structural-properties
#8
Massimiliano Aschi, Argante Bozzi, Carla Luzi, Nadia Bouchemal, Marco Sette
A joint application of experimental and computational approaches has revealed the exceptionally high attitude of crabrolin, a 13-residue peptide with sequence FLPLILRKIVTAL-NH2 , to adopt alpha-helix conformation not only in membrane-mimicking solvents but also in the presence of a not negligible amount of water. Our study shows that this propensity essentially resides in the intrinsic thermodynamic stability of alpha-helix conformation whose kinetic stability is drastically reduced in water solvent. Our analysis suggests that this is due to two effects enhanced by water: a more local effect consisting of the demolition of intra-peptide H-bonds, essential for the alpha-helix formation, and a bulk - electrostatic - effect favoring conformational states more polar than alpha-helix...
June 5, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28580683/simple-method-to-assess-stability-of-immobilized-peptide-ligands-against-proteases
#9
Silvana L Giudicessi, María L Salum, Soledad L Saavedra, María C Martínez-Ceron, Osvaldo Cascone, Rosa Erra-Balsells, Silvia A Camperi
Although peptides are used as affinity chromatography ligands, they could be digested by proteases. Usually, peptide stability is evaluated in solution, which differs from the resin-bounded peptide behavior. Furthermore, the study of the degradation products requires purification steps before analysis. Here, we describe an easy method to assess immobilized peptide stability. Sample peptides were synthesized on hydroxymethylbenzamide-ChemMatrix resin. Peptidyl-resin beads were then incubated with solutions containing proteases...
June 5, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28543807/aromatic-interaction-mediated-inhibition-of-%C3%AE-amyloid-assembly-structures-and-cytotoxicity
#10
Hanyi Xie, Jiaxi Peng, Changliang Liu, Xiaocui Fang, Hongyang Duan, Yimin Zou, Yanlian Yang, Chen Wang
Abnormal aggregation of β-amyloid (Aβ) peptide plays an important role in the onset and progress of Alzheimer's disease (AD); hence, targeting Aβ aggregation is considered as an effective therapeutic strategy. Here, we studied the aromatic-interaction-mediated inhibitory effect of oligomeric polypeptides (K8Y8, K4Y8, K8W8) on Aβ42 fibrillization process. The polypeptides containing lysine as well as representative aromatic amino acids of tryptophan or tyrosine were found to greatly suppress the aggregation as evaluated by thioflavin T assay...
May 23, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28466607/conformational-latitude-activity-relationship-of-kppr-tetrapeptide-analogues-toward-their-ability-to-inhibit-binding-of-vascular-endothelial-growth-factor-165-to-neuropilin-1
#11
Bartlomiej Fedorczyk, Piotr F J Lipiński, Dagmara Tymecka, Anna K Puszko, Beata Wilenska, Gerard Y Perret, Aleksandra Misicka
Neuropilin-1 has been found to be overexpressed in several kinds of malignant tumors, and it is postulated that its interaction with the vascular endothelial growth factor 165 leads to progression of tumor vascularization and growth. Several analogues (KxxR) with various conformational latitudes have been synthesized and found as inhibitors of NRP-1. Detailed insight provided by molecular dynamics simulation allowed forming a clear relationship between flexibility of xx part of the molecule and its inhibitory activity...
May 3, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28466571/synthesis-of-relaxin-2-and-insulin-like-peptide-5-enabled-by-novel-tethering-and-traceless-chemical-excision
#12
Kishore Thalluri, Binbin Kou, Xu Yang, Alexander N Zaykov, John P Mayer, Vasily M Gelfanov, Fa Liu, Richard D DiMarchi
This report presents an entirely chemical, general strategy for the synthesis of relaxin-2 and insulin-like peptide 5. Historically, these two peptides have represented two of the more synthetically challenging members of the insulin superfamily. The key synthetic steps involve two sequential oxime ligations to covalently link the individual A-chain and B-chain, followed by disulfide bond formation under aqueous, redox conditions. This is followed by two chemical reactions that employ diketopiperazine cyclization-mediated cleavage and ester hydrolysis to liberate the connecting peptide and the heterodimeric product...
May 3, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28449250/self-assembly-of-peptide-boroxoles-on-cis-dihydroxylated-oligoamide-templates-in-water
#13
André Wuttke, Armin Geyer
We develop templates that can be used to stabilize consistent oligomers of a bioactive peptide. In the present study, we synthesize oligomers of an antibody epitope from the amyloidogenic prion protein. Dynamic covalent chemistry is the basis for the spontaneous condensation of 2, 3, 4 or 6 peptides with qualified polyol templates presenting the required number of bioorthogonal ligation sites. To study this process in aqueous solution, the N-terminal amino acid of a 13-mer peptide is first acylated with 4-carboxy-benzoboroxole (1-hydroxy-1,3-dihydrobenzo[c][1,2] oxaborole-5-carboxylic acid) and then mixed with the template to obtain self-assembled miniamyloids of specified degree of oligomerization...
April 27, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28429419/semi-synthesis-of-murine-prion-protein-by-native-chemical-ligation-and-chemical-activation-for-preparation-of-polypeptide-%C3%AE-thioester
#14
Lei Shi, Huai Chen, Si-Yu Zhang, Ting-Ting Chu, Yu-Fen Zhao, Yong-Xiang Chen, Yan-Mei Li
Prions are suspected as pathogen of the fatal transmissible spongiform encephalopathies. Strategies to access homogenous prion protein (PrP) are required to fully comprehend the molecular mechanism of prion diseases. However, the polypeptide fragments from PrP show a high tendency to form aggregates, which is a gigantic obstacle of protein synthesis and purification. In this study, murine prion sequence 90 to 230 that is the core three-dimensional structure domain was constructed from three segments murine PrP (mPrP)(90-177), mPrP(178-212), and mPrP(213-230) by combining protein expression, chemical synthesis and chemical ligation...
April 21, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28429417/immobilization-methods-for-the-rapid-total-chemical-synthesis-of-proteins-on-microtiter-plates
#15
Robert Zitterbart, Michael Krumrey, Oliver Seitz
The chemical synthesis of proteins typically involves the solid-phase peptide synthesis of unprotected peptide fragments that are stitched together in solution by native chemical ligation (NCL). The process is slow, and throughput is limited because of the need for repeated high performance liquid chromatography purification steps after both solid-phase peptide synthesis and NCL. With an aim to provide faster access to functional proteins and to accelerate the functional analysis of synthetic proteins by parallelization, we developed a method for the high performance liquid chromatography-free synthesis of proteins on the surface of microtiter plates...
April 21, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28425159/n-terminal-diproline-and-charge-group-effects-on-the-stabilization-of-helical-conformation-in-alanine-based-short-peptides-cd-studies-with-water-and-methanol-as-solvent
#16
Bhupesh Goyal, Kinshuk Raj Srivastava, Susheel Durani
Protein folding problem remains a formidable challenge as main chain, side chain and solvent interactions remain entangled and have been difficult to resolve. Alanine-based short peptides are promising models to dissect protein folding initiation and propagation structurally as well as energetically. The effect of N-terminal diproline and charged side chains is assessed on the stabilization of helical conformation in alanine-based short peptides using circular dichroism (CD) with water and methanol as solvent...
April 20, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28425152/nmr-structures-and-molecular-dynamics-simulation-of-hylin-a1-peptide-analogs-interacting-with-micelles
#17
Edson Crusca, Amanda Souza Câmara, Carolina Oliveira Matos, Reinaldo Marchetto, Eduardo Maffud Cilli, Luciano Morais Lião, Aline Lima de Oliveira
Antimicrobial peptides are recognized candidates with pharmaceutical potential against epidemic emerging multi-drug resistant bacteria. In this study, we use nuclear magnetic resonance spectroscopy and molecular dynamics simulations to determine the unknown structure and evaluate the interaction with dodecylphosphatidylcholine (DPC) and sodium dodecylsulphate (SDS) micelles with three W(6) -Hylin-a1 analogs antimicrobial peptides (HyAc, HyK, and HyD). The HyAc, HyK, and HyD bound to DPC micelles are all formed by a unique α-helix structure...
April 20, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28378383/effects-of-replacement-and-addition-of-an-amino-acid-contained-in-a-cyclic-peptide-corresponding-to-a-%C3%AE-hairpin-loop-sequence-of-human-egf-receptor
#18
Kazuya Kobayashi, Takaaki Mizuguchi, Yasunao Hattori, Naho Ohara, Ryunosuke Ninomiya, Mika Iida, Honami Ooe, Yukako Yamazaki, Minami Takata, Hirokazu Tamamura, Kenichi Akaji
Effects of replacement and addition of an amino acid in a cyclic decapeptide 1 (cyclic-CYNPTTYQMC) for inhibitory activity to dimerization of human epidermal growth factor receptor (EGFR) were examined. By alanine scanning of 1 corresponding to the arm structure (residues 246-254) of a β-hairpin loop sequence (residues 242-259) of EGFR, it was confirmed that replacement of any amino acid in the loop structure lowered the dimerization inhibitory activity of 1. Among the residues examined, Tyr at position 246 and Thr at 250 were found to be crucial for dimer formation...
April 4, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28378376/fluorescent-and-luminescent-fusion-proteins-for-analyses-of-amyloid-beta-peptide-aggregation
#19
Kenji Usui, Masayasu Mie, Takashi Andou, Hisakazu Mihara, Eiry Kobatake
The amyloid beta (Aβ) peptide is regarded as a causative agent of Alzheimer's disease. In this study, fluorescent and luminescent fusion proteins were constructed to analyze Aβ aggregation. A system was developed to monitor changes in luminescence that provides information about Aβ aggregation. In the presence of monomeric Aβ, the fusion protein exhibits higher luminescence intensity, and the luminescence intensity is diminished after aggregation of the fusion protein and Aβ. In contrast, the fluorescence is sustained in the presence of Aβ...
April 4, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28371154/synthesis-of-hemithioindigo-based-chromopeptides-by-using-the-tmb-auxiliary-in-native-chemical-ligation-studies
#20
S Kitzig, K Rück-Braun
The 4,5,6-trimethoxy-2-mercaptobenzyl auxiliary was used in auxiliary-based native chemical ligation reactions with Boc-protected pHTI and mHTI ω-amino acid thioesters 2a,b for the construction of small hemithioindigo (HTI)-based chromopeptides 6a,b with a class 1 PDZ binding motif. While reversible tris(2-carboxyethyl)phosphine (TCEP)-HTI adduct formation required moderate use of access TCEP, the Na ascorbate concentration was broadly varied for optimization of the reaction conditions. In the studies presented, the mHTI ω-amino acid thioester 2b proved to be slightly less reactive than the pHTI ω-amino acid thioester 2a...
March 30, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
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