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Journal of Peptide Science,Volume 24, Issue 3, March 2018. (Source: Journal of Peptide Science)
Source: Journal of Peptide Science - February 12, 2018 Category: Biochemistry Source Type: research
4 ‐Fluorophenyl 3‐nitro‐2‐pyridinesulfenate as a practical protecting agent for amino acids
We report a new protecting agent (1, Npys‐OPh(pF)) for 3‐nitro‐2‐pyridine (Npy) sulfenylation of amino, hydroxy, and thiol functional groups. Several Npys phenoxides were synthesized from Npys chloride (Npys‐Cl) and phenols in the presence of base in 1‐step reaction, and their ability for Npy‐sulfenylation was evaluated. As a result, 1 was selected as a new Npy‐sulfenylation agent with advantages including improved physicochemical stability, more controllable reactivity, and easier handling than the conventional protecting agent Npys‐Cl.
We developed a new protecting reagent, 4‐fluorophenyl 3‐nitro...
Source: Journal of Peptide Science - February 1, 2018 Category: Biochemistry Authors: Yan Cui, C édric Rentier, Akihiro Taguchi, Kentaro Takayama, Atsuhiko Taniguchi, Yoshio Hayashi Tags: RAPID COMMUNICATION Source Type: research
Respirable powder formulation of a shortened vasoactive intestinal peptide analog for treatment of airway inflammatory diseases
The aim of present study was to develop a respirable powder (RP) of a shortened vasoactive intestinal peptide (VIP) analog for inhalation. VIP and C‐terminally truncated VIP analogs were synthesized with a solid‐phase method. A structure‐activity relationship (SAR) study was carried out in terms with binding and relaxant activities of the peptides. Prepared RP formulation of a shortened VIP analog was physicochemically characterized by morphological, in vitro aerodynamic, and pharmacological assessments. The SAR study demonstrated that the N‐terminal 23 amino acid residues were required for biological activity of V...
Source: Journal of Peptide Science - February 1, 2018 Category: Biochemistry Authors: Hiroki Suzuki, Takahiro Mizumoto, Yoshiki Seto, Hideyuki Sato, Satomi Onoue Tags: RESEARCH ARTICLE Source Type: research
Antifungal dipeptides incorporating an inhibitor of homoserine dehydrogenase
The antifungal activity of 5‐hydroxy‐4‐oxo‐l‐norvaline (HONV), exhibited under conditions mimicking human serum, may be improved upon incorporation of this amino acid into a dipeptide structure. Several HONV‐containing dipeptides inhibited growth of human pathogenic yeasts of the Candida genus in the RPMI‐1640 medium, with minimal inhibitory concentration values in the 32 to 64 μg mL−1 range. This activity was not affected by multidrug resistance that is caused by overexpression of genes encoding drug efflux proteins. The mechanism of antifungal action of HONV dipeptides involved uptake by the oligopepti...
Source: Journal of Peptide Science - January 11, 2018 Category: Biochemistry Authors: Andrzej S. Skwarecki, Marta Schielmann, Dorota Martynow, Marcin Kawczy ński, Aleksandra Wiśniewska, Maria J. Milewska, Sławomir Milewski Tags: RESEARCH ARTICLE Source Type: research
Design, expression, and characterization of the hybrid antimicrobial peptide T ‐catesbeianin‐1 based on FyuA
The overuse of antibiotics has resulted in the emergence of antibiotic‐resistant bacteria, which presents an urgent need for new antimicrobial agents. At present, antimicrobial peptides have attracted a great deal of attention from researchers. However, antimicrobial peptides often affect a broad range of microorganisms, including the normal flora in a host organism. In the present study, we designed a novel hybrid antimicrobial peptide, expressed the hybrid peptide, and studied its specific target. The hybrid peptide, named T‐catesbeianin‐1, which includes the FyuA‐binding domain of pesticin and the peptide catesb...
Source: Journal of Peptide Science - January 11, 2018 Category: Biochemistry Authors: Huihui Xu, Kunyuan Tie, Yang Zhang, Xin Feng, Yuan Cao, Wenyu Han Tags: RESEARCH ARTICLE Source Type: research
Molecular characterization of the β‐amyloid(4‐10) epitope of plaque specific Aβ antibodies by affinity‐mass spectrometry using alanine site mutation
Alzheimer disease is a neurodegenerative disease affecting an increasing number of patients worldwide. Current therapeutic strategies are directed to molecules capable to block the aggregation of the β‐amyloid(1‐42) (Aβ) peptide and its shorter naturally occurring peptide fragments into toxic oligomers and amyloid fibrils. Aβ‐specific antibodies have been recently developed as powerful antiaggregation tools. The identification and functional characterization of the epitope structures of Aβ antibodies contributes to the elucidation of their mechanism of action in the human organism. In previous studies, the Aβ(4...
Source: Journal of Peptide Science - January 11, 2018 Category: Biochemistry Authors: Raluca Ștefănescu, Loredana Lupu, Marilena Manea, Roxana E. Iacob, Michael Przybylski Tags: RESEARCH ARTICLE Source Type: research
Max Bergmann award lecture:Macromolecular medicinal chemistry as applied to metabolic diseases
This report reviews advances in macromolecular medicinal chemistry as applied to metabolic diseases, with particular emphasis on contributions from the DiMarchi laboratory in collaboration with multiple international investigators. The design of high potency peptides with balanced biological action at multiple receptors, and advances in synthetic chemistry as applied to insulin‐related peptides are highlighted (Source: Journal of Peptide Science)
Source: Journal of Peptide Science - January 11, 2018 Category: Biochemistry Authors: Richard D. DiMarchi, John P. Mayer, Vasily M. Gelfanov, Matthias Tsch öp Tags: REVIEW Source Type: research
Max ‐Bergmann award lecture:A RaPID way to discover bioactive nonstandard peptides assisted by the flexizyme and FIT systems
Although general review articles should cover various people's achievements related to the subject, this review is privileged to describe the technology developed by Suga (and colleagues) as a recipient of the Max‐Bergmann Medal in 2016. The technology consists of 3 unique and essential tools, flexizymes, FIT, and RaPID systems. This review describes the history of the development of each tool and discusses the recent applications of the RaPID system to discover potent nonstandard peptides for therapeutic and diagnostic uses.
“RaPID (Radom non‐standard Peptides Discovery) system. Selective enrichment of binding‐ac...
Source: Journal of Peptide Science - January 11, 2018 Category: Biochemistry Authors: Hiroaki Suga Tags: REVIEW Source Type: research
Introducing the new journal design for the Journal of Peptide Science
(Source: Journal of Peptide Science)
Source: Journal of Peptide Science - January 11, 2018 Category: Biochemistry Authors: Stephen Raywood Tags: EDITORIAL Source Type: research
Issue information
(Source: Journal of Peptide Science)
Source: Journal of Peptide Science - January 11, 2018 Category: Biochemistry Tags: ISSUE INFORMATION Source Type: research
A practical diastereoselective synthesis of ( −)‐bestatin
Diastereoselective addition of nitromethane to Boc‐D‐Phe‐H in the presence of sodium hydride in diethyl ether/hexane containing 15‐crown‐5 and subsequent N,O‐protection with 2,2‐dimethoxypropane gave trans‐oxazolidine in a diastereomeric ratio of >16:1. The oxazolidine was easily separated by column chromatography, which after Nef reaction was coupled to H‐Leu‐OtBu. The 8‐step synthesis afforded (−)‐bestatin in an overall yield of 24.7% after deprotection and ion exchange.
An 8‐step diastereoselective synthesis of (−)‐bestatin is developed via nitro‐aldol reaction in a nonpolar solvent...
Source: Journal of Peptide Science - January 1, 2018 Category: Biochemistry Authors: Suisheng Shang, Andreas V. Willems, Satendra S. Chauhan Tags: RESEARCH ARTICLE Source Type: research
Assessment of the potential of temporin peptides from the frog Rana temporaria (Ranidae) as anti ‐diabetic agents
Temporin A (FLPLIGRVLSGIL‐NH2), temporin F (FLPLIGKVLSGIL‐NH2), and temporin G (FFPVIGRILNGIL‐NH2), first identified in skin secretions of the frog Rana temporaria, produced concentration‐dependent stimulation of insulin release from BRIN‐BD11 rat clonal β‐cells at concentrations ≥1 nM, without cytotoxicity at concentrations up to 3 μM. Temporin A was the most effective. The mechanism of insulinotropic action did not involve an increase in intracellular Ca2+ concentrations. Temporins B, C, E, H, and K were either inactive or only weakly active. Temporins A, F, and G also produced a concentration‐depende...
Source: Journal of Peptide Science - January 1, 2018 Category: Biochemistry Authors: Vishal Musale, Bruno Casciaro, Maria Luisa Mangoni, Yasser H.A. Abdel ‐Wahab, Peter R. Flatt, J. Michael Conlon Tags: RESEARCH ARTICLE Source Type: research
Amyloid ‐like aggregation of designer bolaamphiphilic peptides: Effect of hydrophobic section and hydrophilic heads
In this study, we showed that a series of designer bolaamphiphilic peptides could undergo amyloid‐like aggregation even though they didn't possess typical β‐sheet secondary structure. Through systematic amino acid substitution, we found that for the self‐assembling ability, the number and species of amino acid in hydrophobic section could be variable as long as enough hydrophobic interaction is provided, while different polar amino acids as the hydrophilic heads could change the self‐assembling nanostructures with their aggregating behaviors affected by pH value change. Based on these results, novel self‐assembl...
Source: Journal of Peptide Science - December 1, 2017 Category: Biochemistry Authors: Feng Qiu, Chengkang Tang, Yongzhu Chen Tags: RESEARCH ARTICLE Source Type: research
Preparation of tri(ethylene glycol) grafted core ‐shell type polymer support for solid‐phase peptide synthesis
A core‐shell type polymer support for solid‐phase peptide synthesis has been developed for high coupling efficiency of peptides and versatile applications such as on‐bead bioassays. Although various kinds of polymer supports have been developed, they have their own drawbacks including poor accessibility of reagents and incompatibility in aqueous solution. In this paper, we prepared hydrophilic tri(ethylene glycol) (TEG) grafted core‐shell type polymer supports (TEG SURE) for efficient solid‐phase peptide synthesis and on‐bead bioassays. TEG SURE was prepared by grafting TEG derivative on the surface of AM PS re...
Source: Journal of Peptide Science - December 1, 2017 Category: Biochemistry Authors: Jaehi Kim, Seojung Kim, Dong ‐Sik Shin, Yoon‐Sik Lee Tags: RESEARCH ARTICLE Source Type: research
Modeling of a C ‐end rule peptide adsorbed onto gold nanoparticles
The RPAR peptide, a prototype C‐end Rule (CendR) sequence that binds to neuropilin‐1 (NRP‐1), has potential therapeutic uses as internalization trigger in anticancer nanodevices. Recently, the functionalization of gold nanoparticles with CendR peptides has been proved to be a successful strategy to target the NRP‐1 receptor in prostate cancer cells. In this work, we investigate the influence of two gold surface facets, (100) and (111), on the conformational preferences of RPAR using molecular dynamics simulations. Both clustering and conformational analyses revealed that the peptide backbone becomes very rigid upon...
Source: Journal of Peptide Science - December 1, 2017 Category: Biochemistry Authors: Jordi Triguero, Alejandra Flores ‐Ortega, David Zanuy, Carlos Alemán Tags: RESEARCH ARTICLE Source Type: research
