A biotinylated peptide, BP21, as a novel potent anti ‐anaphylactic agent targeting platelet‐activating factor
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. In contrast, the anti‐hypothermic effect of BGP21, in which the Tyr‐Lys‐Asp‐Gly sequence in BP21 was modified to a Gly‐Gly‐Gly‐Gly sequence, was less than that of BP21. The alanine scanning and shuffling the amino acid residues of BP4 (Tyr‐Lys...
Source: Journal of Peptide Science - June 1, 2017 Category: Biochemistry Authors: Akira Sato, Keiichi Ebina Tags: Research Article Source Type: research
Stoichiometric analysis of oligomeric states of three class ‐A GPCRs, chemokine‐CXCR4, dopamine‐D2, and prostaglandin‐EP1 receptors, on living cells
In this study, we expanded our study to three well‐studied class‐A GPCRs: C‐X‐C chemokine receptor of stromal cell‐derived factor‐1α (CXCR4), dopamine receptor D2 short isotype (D2R), and prostaglandin E receptor subtype 1 (EP1R). We found that these receptors did not form constitutive homooligomers. The receptors exhibited calcium signaling upon agonist stimulation as monomers, although CXCR4 and EP1R gradually clustered after fast signaling. We conclude that homooligomerization is not necessary for the signal transductions of these four class‐A GPCRs. Copyright © 2017 European Peptide Society and John Wil...
Source: Journal of Peptide Science - June 1, 2017 Category: Biochemistry Authors: Kenichi Kawano, Tetsuya Yagi, Nozomu Fukada, Yoshiaki Yano, Katsumi Matsuzaki Tags: Special Issue Article Source Type: research
Visible ‐light photoredox‐catalyzed desulfurization of thiol‐ and disulfide‐containing amino acids and small peptides
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 6.5 and 7.0 for the cysteine derivatives and gluta...
Source: Journal of Peptide Science - June 1, 2017 Category: Biochemistry Authors: Myungmo Lee, Saskia Neukirchen, Chiara Cabrele, Oliver Reiser Tags: Research Article Source Type: research
Characterization of an insulinotropic peptide from skin secretions of Odorrana andersonii
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...
Source: Journal of Peptide Science - June 1, 2017 Category: Biochemistry Authors: Weijie Shang, Xinwang Yang, Xiaoman Ju, Yueying Xie, Yun Zhang, Wen ‐Hui Lee Tags: Research Article Source Type: research
Cyanobacterial peptides as a prototype for the design of cathepsin D inhibitors
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), cyclo...
Source: Journal of Peptide Science - June 1, 2017 Category: Biochemistry Authors: Hao Xu, Keting Bao, Shuai Tang, Jing Ai, Haiyan Hu, Wei Zhang Tags: Research Article Source Type: research
Crabrolin, a natural antimicrobial peptide: structural properties
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 demo...
Source: Journal of Peptide Science - June 1, 2017 Category: Biochemistry Authors: Massimiliano Aschi, Argante Bozzi, Carla Luzi, Nadia Bouchemal, Marco Sette Tags: Research Article Source Type: research
Aromatic ‐interaction‐mediated inhibition of β‐amyloid assembly structures and cytotoxicity
This study could be beneficial for developing peptide‐based inhibitory agents for amyloidoses. Copyright © 2017 European Peptide Society and John Wiley & Sons, Ltd.
We demonstrate the inhibitory effect of oligomeric polypeptides containing representative aromatic amino acids of tryptophan and tyrosine (K8Y8, K4Y8, K8W8) on Aβ42 fibrillization process. Through direct binding at the N‐terminus of Aβ42 by π–π stacking between aromatic amino acids and Phe19, together with hydrogen bonds, the polypeptides can remarkably weaken the aggregation and fibrillization process of Aβ42, inhabit the β‐sheet formation ...
Source: Journal of Peptide Science - May 23, 2017 Category: Biochemistry Authors: Hanyi Xie, Jiaxi Peng, Changliang Liu, Xiaocui Fang, Hongyang Duan, Yimin Zou, Yanlian Yang, Chen Wang Tags: Research Article Source Type: research
Issue information
(Source: Journal of Peptide Science)
Source: Journal of Peptide Science - May 15, 2017 Category: Biochemistry Tags: Issue Information Source Type: research
Synthesis of relaxin ‐2 and insulin‐like peptide 5 enabled by novel tethering and traceless chemical excision
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 produ...
Source: Journal of Peptide Science - May 3, 2017 Category: Biochemistry Authors: Kishore Thalluri, Binbin Kou, Xu Yang, Alexander N. Zaykov, John P. Mayer, Vasily M. Gelfanov, Fa Liu, Richard D. DiMarchi Tags: Research Article Source Type: research
Conformational latitude – activity relationship of KPPR tetrapeptide analogues toward their ability to inhibit binding of vascular endothelial growth factor 165 to neuropilin‐1
Neuropilin‐1 (NRP‐1) has been found to be overexpressed in several kinds of malignant tumors, and it is postulated that in pathological angiogenesis, its interaction with the vascular endothelial growth factor 165 (VEGF165) leads to progression of tumor vascularization and growth. Herein, we present synthesis and in vitro evaluation of tetrapeptides with the general sequence KxxR, where xx represents two canonical amino acid residues or a single amino acid possessing hydrocarbon backbone. All synthesized compounds were found to be inhibitors of VEGF165/NRP‐1 interactions. The rationale behind their design was to eluc...
Source: Journal of Peptide Science - May 1, 2017 Category: Biochemistry Authors: Bartlomiej Fedorczyk, Piotr F. J. Lipi ński, Dagmara Tymecka, Anna K. Puszko, Beata Wilenska, Gerard Y. Perret, Aleksandra Misicka Tags: Research Article Source Type: research
Self ‐assembly of peptide boroxoles on cis‐dihydroxylated oligoamide templates in water
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...
Source: Journal of Peptide Science - April 27, 2017 Category: Biochemistry Authors: Andr é Wuttke, Armin Geyer Tags: Research Article Source Type: research
Semi ‐synthesis of murine prion protein by native chemical ligation and chemical activation for preparation of polypeptide‐α‐thioester
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. The protein sequence 90 to 177 was obtained from expression and finally converted into the polypeptide hydrazide by chemical activation of a cysteine in the tail. The other two polypeptide fragments of the C‐terminal were obtained by chemical synthesis, which utilized the strategies of isopeptide and pseudoproline building blocks to complete the sy...
Source: Journal of Peptide Science - April 21, 2017 Category: Biochemistry Authors: Lei Shi, Huai Chen, Si ‐Yu Zhang, Ting‐Ting Chu, Yu‐Fen Zhao, Yong‐Xiang Chen, Yan‐Mei Li Tags: Research Article Source Type: research
Immobilization methods for the rapid total chemical synthesis of proteins on microtiter plates
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 o...
Source: Journal of Peptide Science - April 21, 2017 Category: Biochemistry Authors: Robert Zitterbart, Michael Krumrey, Oliver Seitz Tags: Special Issue Article Source Type: research
NMR structures and molecular dynamics simulation of hylin ‐a1 peptide analogs interacting with micelles
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 W6‐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. Moreover, all peptides reach the DPC micelles' core, which thus suggests that the N‐terminal modifications do not influence the interaction with zwiterionic surfaces. On the other hand, only HyAc and HyK peptides ...
Source: Journal of Peptide Science - April 20, 2017 Category: Biochemistry Authors: Edson Crusca, Amanda Souza C âmara, Carolina Oliveira Matos, Reinaldo Marchetto, Eduardo Maffud Cilli, Luciano Morais Lião, Aline Lima de Oliveira Tags: Research Article Source Type: research
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
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. A1 (Ac–Pro–Pro–Ala–Lys–Ala–Lys–Ala–Lys–Ala–NH2) is designed to assess the effect of N‐...
Source: Journal of Peptide Science - April 20, 2017 Category: Biochemistry Authors: Bhupesh Goyal, Kinshuk Raj Srivastava, Susheel Durani Tags: Research Article Source Type: research
