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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/28466607/conformational-latitude-activity-relationship-of-kppr-tetrapeptide-analogues-toward-their-ability-to-inhibit-binding-of-vascular-endothelial-growth-factor-165-to-neuropilin-1
#1
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
#2
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
#3
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
#4
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
#5
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
#6
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
#7
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
#8
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
#9
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
#10
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
https://www.readbyqxmd.com/read/28370688/impact-of-the-amino-acid-sequence-on-the-conformation-of-side-chain-lactam-bridged-octapeptides
#11
Saskia Neukirchen, Viktoria Krieger, Cornelia Roschger, Mario Schubert, Brigitta Elsässer, Chiara Cabrele
Synthetic helical peptides are valuable scaffolds for the development of modulators of protein-protein interactions involving helical motifs. Backbone-to-side chain or side chain-to-side chain constraints have been and still are intensively exploited to stabilize short α-helices. Very often, these constraints have been combined with backbone modifications induced by Cα-tetrasubstituted, β-, or γ-amino acids, which facilitate the α-peptide or α/β/γ-peptide adopting an α-helical conformation. In this work, we investigated the helical character of octapeptides that were cyclized by a Lys-Asp-(i,i + 4)-lactam bridge...
March 29, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28370673/generation-of-monoclonal-antibodies-against-mitocryptide-2-toward-a-new-strategy-to-investigate-the-biological-roles-of-cryptides
#12
Tatsuya Hattori, Takenori Yamada, Hiroki Morikawa, Takayuki Marutani, Koki Tsutsumi, Kodai Nishino, Toshihiro Shimizu, Yoshisuke Nishi, Yoshiaki Kiso, Hidehito Mukai
We recently identified a novel family of neutrophil-activating peptides including mitocryptide-1 and mitocryptide-2 (MCT-2) that are endogenously produced from various mitochondrial proteins. Among them, MCT-2 is an N-formylated pentadecapeptide derived from mitochondrial cytochrome b and is found to promote neutrophilic migration and phagocytosis efficiently. Signaling mechanisms of neutrophil activation by MCT-2 have been investigated at the cellular level, and MCT-2 has been demonstrated to be an endogenous specific ligand for formyl peptide receptor-2 (also referred to as formyl peptide receptor-like 1)...
March 29, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28332260/biological-characterization-of-novel-nitroimidazole-peptide-conjugates-in-vitro-and-in-vivo
#13
Ralf Bergmann, Katrin Splith, Jens Pietzsch, Michael Bachmann, Ines Neundorf
Recently, we reported on the design of a multimodal peptide conjugate useful as delivery platform for targeting hypoxic cells. A nitroimidazole (2-(2-nitroimidazol-1-yl)acetic acid, NIA) moiety, which is selectively entrapped in hypoxic cells, was coupled to a cell-penetrating peptide serving as the transporter. Furthermore, attachment of a bifunctional linker allowed the introduction of a diagnostic or therapeutic radiometal. However, although selective tumor accumulation could be detected in vivo, a fast renal clearance of the compound was observed...
March 23, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28332258/n-terminal-chemical-protein-labeling-using-the-naturally-split-gos-terl-intein
#14
Anne-Lena Bachmann, Henning D Mootz
Chemoselective and regioselective chemical protein labeling is of great importance, yet no current technique is sufficiently general and simple to perform. Protein trans-splicing by split inteins can be used to ligate short tags with chemical labels to either the N or the C terminus of a protein. The CysTag approach exploits split intein fragments without a cysteine fused with such a short tag containing a single cysteine that is easily amenable to selective modification using classical cysteine bioconjugation...
March 23, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28326661/role-of-single-disulfide-linkages-in-the-folding-and-activity-of-scyllatoxin-based-bh3-domain-mimetics
#15
Danushka Arachchige, M Margaret Harris, Zachary Coon, Jacob Carlsen, Justin M Holub
Anti-apoptotic Bcl-2 proteins are implicated in pathogenic cell survival and have attracted considerable interest as therapeutic targets. We recently developed a class of synthetic peptide based on scyllatoxin (ScTx) designed to mimic the helical BH3 interaction domain of the pro-apoptotic Bcl-2 protein Bax. In this communication, the contribution of single disulfides in the folding and function of ScTx-Bax peptides was investigated. We synthesized five ScTx-Bax variants, each presenting a different combination of native disulfide linkage and evaluated their ability to directly bind Bcl-2 in vitro...
March 22, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28299865/novel-short-antimicrobial-peptide-isolated-from-xenopus-laevis-skin
#16
Yu Zhang, Songcai Liu, Siming Li, Yunyun Cheng, Linyan Nie, Gang Wang, Chen Lv, Wenzhen Wei, Cheng Cheng, Feng Hou, Linlin Hao
A rich source of bioactive peptides, including a large number of antimicrobial peptides, has been found in amphibian skin. In this study, a novel short antimicrobial peptide was purified from Xenopus laevis skin and characterised through reversed-phase high-performance liquid chromatography, Edman degradation and matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry. The peptide was composed of six amino acids with a sequence of DEDLDE and thus named X. laevis antibacterial peptide-P2 (XLAsp-P2)...
March 16, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28299840/antimicrobial-activity-and-stability-of-protonectin-with-d-amino-acid-substitutions
#17
Shuai Qiu, Ranran Zhu, Yanyan Zhao, Xiaoping An, Fengjing Jia, Jinxiu Peng, Zelin Ma, Yuanyuan Zhu, Jiayi Wang, Jinhuan Su, Qingjun Wang, Hailin Wang, Yuan Li, Kairong Wang, Wenjin Yan, Rui Wang
The misuse and overuse of antibiotics result in the emergence of resistant bacteria and fungi, which make an urgent need of the new antimicrobial agents. Nowadays, antimicrobial peptides have attracted great attention of researchers. However, the low physiological stability in biological system limits the application of naturally occurring antimicrobial peptides as novel therapeutics. In the present study, we synthesized derivatives of protonectin by substituting all the amino acid residues or the cationic lysine residue with the corresponding D-amino acids...
March 16, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28271599/peptides-recent-developments-and-future-directions-at-the-15th-naples-workshop-on-bioactive-peptides
#18
EDITORIAL
Giancarlo Morelli
No abstract text is available yet for this article.
March 8, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28247497/centipede-venom-peptide-ssmtx-i-with-two-intramolecular-disulfide-bonds-shows-analgesic-activities-in-animal-models
#19
Ying Wang, Xiaojie Li, Meifeng Yang, Chunyun Wu, Zhirong Zou, Jing Tang, Xinwang Yang
Pain is a major symptom of many diseases and results in enormous pressures on human body or society. Currently, clinically used analgesic drugs, including opioids and nonsteroidal anti-inflammatory drugs, have adverse reactions, and thus, the development of new types of analgesic drug candidates is urgently needed. Animal venom peptides have proven to have potential as new types of analgesic medicine. In this research, we describe the isolation and characterization of an analgesic peptide from the crude venom of centipede, Scolopendra subspinipes mutilans...
March 1, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/28421689/on-resin-n-formylation-of-peptides-a-head-to-head-comparison-of-reagents-in-solid-phase-synthesis-of-ligands-for-formyl-peptide-receptors
#20
Simon Bendt Christensen, Anna Mette Hansen, Henrik Franzyk
4-Nitrophenyl formate was found to be the most convenient reagent in solid-phase formylation of peptides with a high formylation degree within 20 min to 3 h depending on reaction temperature and length of peptide.
May 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
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