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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/29446187/4-fluorophenyl-3-nitro-2-pyridinesulfenate-as-a-practical-protecting-agent-for-amino-acids
#1
Yan Cui, Cédric Rentier, Akihiro Taguchi, Kentaro Takayama, Atsuhiko Taniguchi, Yoshio Hayashi
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...
February 15, 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29441631/respirable-powder-formulation-of-a-shortened-vasoactive-intestinal-peptide-analog-for-treatment-of-airway-inflammatory-diseases
#2
Hiroki Suzuki, Takahiro Mizumoto, Yoshiki Seto, Hideyuki Sato, Satomi Onoue
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 VIP...
February 14, 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29430772/a-practical-diastereoselective-synthesis-of-bestatin
#3
Suisheng Shang, Andreas V Willems, Satendra S Chauhan
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.
February 12, 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29349894/assessment-of-the-potential-of-temporin-peptides-from-the-frog-rana-temporaria-ranidae-as-anti-diabetic-agents
#4
Vishal Musale, Bruno Casciaro, Maria Luisa Mangoni, Yasser H A Abdel-Wahab, Peter R Flatt, J Michael Conlon
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...
January 19, 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29239498/amyloid-like-aggregation-of-designer-bolaamphiphilic-peptides-effect-of-hydrophobic-section-and-hydrophilic-heads
#5
Feng Qiu, Chengkang Tang, Yongzhu Chen
Amyloid-like aggregation of natural proteins or polypeptides is an important process involved in many human diseases as well as some normal biological functions. Plenty of works have been done on this ubiquitous phenomenon, but the molecular mechanism of amyloid-like aggregation has not been fully understood yet. 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...
December 14, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29235177/preparation-of-tri-ethylene-glycol-grafted-core-shell-type-polymer-support-for-solid-phase-peptide-synthesis
#6
Jaehi Kim, Seojung Kim, Dong-Sik Shin, Yoon-Sik Lee
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...
December 13, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29231280/modeling-of-a-c-end-rule-peptide-adsorbed-onto-gold-nanoparticles
#7
Jordi Triguero, Alejandra Flores-Ortega, David Zanuy, Carlos Alemán
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...
December 12, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29159976/design-and-study-of-lipopeptide-inhibitors-on-preventing-aggregation-of-human-islet-amyloid-polypeptide-residues-11-20
#8
Yexuan Mao, Lanlan Yu, Mengfan Mao, Chuanguo Ma, Lingbo Qu
Type 2 diabetes mellitus, a kind of conformational disease, has become an epidemic disease, which seriously endangers the quality of life and health of human beings. The deposition of human islet amyloid polypeptide (hIAPP) has been considered as one of the major pathological features of type 2 diabetes mellitus. As lipopeptides have some hydrophobic groups, which are similar to the reported aggregation inhibitors, and some lipopeptides could prevent cells from depositing of amyloid fibrils, several potential lipopeptide inhibitors have been engineered and synthesized, which have been assessed for their inhibitory effect in preventing amyloid fibrils formation of hIAPP11-20 by using the conventional thioflavin-T fluorescence assay and new technique microscale thermophoresis (MST)...
November 21, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29436155/design-of-cyclic-and-d-amino-acids-containing-peptidomimetics-for-inhibition-of-protein-protein-interactions-of-her2-her3
#9
Sandeep Pallerla, Himgauri Naik, Sitanshu Singh, Ted Gauthier, Rushikesh Sable, Seetharama D Jois
HER2 receptors are surface proteins belonging to the epidermal growth factor family of receptors. Their numbers are elevated in breast, lung, and ovarian cancers. HER2-positive cancers are aggressive, have higher mortality rate, and have a poor prognosis. We have designed peptidomimetics that bind to HER2 and block the HER2-mediated dimerization of epidermal growth factor family of receptors. Among these, a symmetrical cyclic peptidomimetic (compound 18) exhibited antiproliferative activity in HER2-overexpressing lung cancer cell lines with IC50 values in the nanomolar concentration range...
February 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29436154/new-methodology-for-automated-spot-synthesis-of-peptides-on-cellulose-using-1-3-5-triazine-derivatives-as-linkers-and-as-coupling-reagents
#10
Justyna Fraczyk, Małgorzata Walczak, Zbigniew J Kaminski
Two new rigid bi-aromatic linkers for synthesis of peptide arrays by SPOT methodology were obtained from cellulose treated with 2,4-dichloro-6-methoxy-1,3,5-triazine. Reaction with m-phenylenediamine gave non-cleavable TYPE I linker which enabled attachment of the peptides via resistant to harsh reaction conditions amide, ether, and amine bonds. Reaction with 3-Fmoc-aminobenzoic acid followed by thermal isomerization of the intermediate "superactive" ester producing an amide-like bond gave TYPE II linker that was very stable during peptide synthesis...
February 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29322652/introducing-the-new-journal-design-for-the-journal-of-peptide-science
#11
EDITORIAL
Stephen Raywood
No abstract text is available yet for this article.
January 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29322651/antifungal-dipeptides-incorporating-an-inhibitor-of-homoserine-dehydrogenase
#12
Andrzej S Skwarecki, Marta Schielmann, Dorota Martynow, Marcin Kawczyński, Aleksandra Wiśniewska, Maria J Milewska, Sławomir Milewski
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...
January 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29322650/molecular-characterization-of-the-%C3%AE-amyloid-4-10-epitope-of-plaque-specific-a%C3%AE-antibodies-by-affinity-mass-spectrometry-using-alanine-site-mutation
#13
Raluca Ștefănescu, Loredana Lupu, Marilena Manea, Roxana E Iacob, Michael Przybylski
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...
January 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29322649/design-expression-and-characterization-of-the-hybrid-antimicrobial-peptide-t-catesbeianin-1-based-on-fyua
#14
Huihui Xu, Kunyuan Tie, Yang Zhang, Xin Feng, Yuan Cao, Wenyu Han
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 catesbeianin-1, was designed and expressed in Pichia pastoris X-33...
January 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29322648/max-bergmann-award-lecture-a-rapid-way-to-discover-bioactive-nonstandard-peptides-assisted-by-the-flexizyme-and-fit-systems
#15
Hiroaki Suga
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...
January 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29322647/max-bergmann-award-lecture-macromolecular-medicinal-chemistry-as-applied-to-metabolic-diseases
#16
REVIEW
Richard D DiMarchi, John P Mayer, Vasily M Gelfanov, Matthias Tschöp
This review presents the scope of research presented in an October 2016 lecture pertaining to the award of the 2015 Max Bergmann Medal. The advancement in synthetic and biosynthetic chemistry as applied to the discovery of novel macromolecular drug candidates is reviewed. The evolution of the technology from the design, synthesis, and development of the first biosynthetic peptides through the emergence of peptide-based incretin agonists that function by multiple biological mechanisms is exemplified by the progression of such peptides from preclinical to clinical study...
January 2018: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29193518/antimicrobial-activity-of-the-indolicidin-derived-novel-synthetic-peptide-in-58
#17
A S Vasilchenko, A V Vasilchenko, T M Pashkova, M P Smirnova, N I Kolodkin, I V Manukhov, G B Zavilgelsky, E A Sizova, O L Kartashova, A S Simbirtsev, E A Rogozhin, G K Duskaev, M V Sycheva
Natural peptides with antimicrobial activity are extremely diverse, and peptide synthesis technologies make it possible to significantly improve their properties for specific tasks. Here, we investigate the biological properties of the natural peptide indolicidin and the indolicidin-derived novel synthetic peptide In-58. In-58 was generated by replacing all tryptophan residues on phenylalanine in D-configuration; the α-amino group in the main chain also was modified by unsaturated fatty acid. Compared with indolicidin, In-58 is more bactericidal, more resistant to proteinase K, and less toxic to mammalian cells...
December 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29193517/biological-consequences-of-improving-the-structural-stability-of-hairpins-that-have-antimicrobial-activity
#18
Kalkena Sivanesam, Brandon L Kier, Samuel D Whedon, Champak Chatterjee, Niels H Andersen
Designing new antimicrobial peptides (AMPs) focuses heavily on the activity of the peptide and less on the elements that stabilize the secondary structure of these peptides. Studies have shown that improving the structure of naturally occurring AMPs can affect activity and so here we explore the relationship between structure and activity of two non-naturally occurring AMPs. We have used a backbone-cyclized peptide as a template and designed an uncyclized analogue of this peptide that has antimicrobial activity...
December 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29110415/structural-and-functional-studies-of-differentially-o-glycosylated-analogs-of-a-thrombin-inhibitory-peptide-variegin
#19
Pidathala R V Shabareesh, Ashish Kumar, Dinakar M Salunke, Kanwal J Kaur
Variegin is a 32-amino acid long thrombin inhibitory peptide isolated from the salivary gland extract of tropical bont tick Amblyomma variegatum. It was identified to be O-glycosylated on its Thr-14 side chain, and this glycosylated form was 14-fold more potent than that of its non-glycosylated form. However, as the identity of this glycosylation remained elusive, the mechanistic details underlying its functional impact are not yet known. In this report, we synthesized four different O-glycosylated analogs of variegin bearing physiologically relevant sugars on its Thr-14...
November 7, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
https://www.readbyqxmd.com/read/29110375/modulation-of-immunogenicity-of-poly-sarcosine-displayed-on-various-nanoparticle-surfaces-due-to-different-physical-properties
#20
Cheol Joo Kim, Eri Hara, Naoki Watabe, Isao Hara, Shunsaku Kimura
Poly(sarcosine) displayed on polymeric micelle is reported to trigger a T cell-independent type2 reaction with B1a cells in the mice to produce IgM and IgG3 antibodies. In addition to polymeric micelle, three kinds of vesicles displaying poly(sarcosine) on surface were prepared here to evaluate the amounts and avidities of IgM and IgG3, which were produced in mice, to correlate them with physical properties of the molecular assemblies. The largest amount of IgM was produced after twice administrations of a polymeric micelle of 35 nm diameter (G1)...
November 7, 2017: Journal of Peptide Science: An Official Publication of the European Peptide Society
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