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Peptide synthesis

Noam Brown, Jiangtao Lei, Chendi Zhan, Linda J W Shimon, Lihi Adler-Abramovich, Guanghong Wei, Ehud Gazit
Self-assembly is a process of key importance in natural systems and in nanotechnology. Peptides are attractive building blocks due to their relative facile synthesis, biocompatibility and other unique properties. Diphenylalanine (FF) and its derivatives are known to form nanostructures of various architectures and remarkable characteristics. The larger triphenylalanine (FFF) was found to self-assemble as efficiently as FF, forming related but distinct architectures of plate-like and spherical nanostructures...
March 20, 2018: ACS Nano
Kristal Jesús-de la Cruz, Carlos Alfonso Álvarez-González, Emyr Peña, José Antonio Morales-Contreras, Ángela Ávila-Fernández
In fishes, trypsins are adapted to different environmental conditions, and the biochemical and kinetic properties of a broad variety of native isoforms have been studied. Proteolytic enzymes remain in high demand in the detergent, food, and feed industries; however, our analysis of the literature showed that, in the last decade, some fish trypsins have been studied for the synthesis of industrial peptides and for specific biomedical uses as antipathogenic agents against viruses and bacteria, which have been recently patented...
April 2018: 3 Biotech
Joseph M Rogers, Sunbum Kwon, Simon J Dawson, Pradeep K Mandal, Hiroaki Suga, Ivan Huc
Translation, the mRNA-templated synthesis of peptides by the ribosome, can be manipulated to incorporate variants of the 20 cognate amino acids. Such approaches for expanding the range of chemical entities that can be produced by the ribosome may accelerate the discovery of molecules that can perform functions for which poorly folded, short peptidic sequences are ill suited. Here, we show that the ribosome tolerates some artificial helical aromatic oligomers, so-called foldamers. Using a flexible tRNA-acylation ribozyme-flexizyme-foldamers were attached to tRNA, and the resulting acylated tRNAs were delivered to the ribosome to initiate the synthesis of non-cyclic and cyclic foldamer-peptide hybrid molecules...
March 19, 2018: Nature Chemistry
Davoud Mozhdehi, Kelli M Luginbuhl, Joseph R Simon, Michael Dzuricky, Rüdiger Berger, H Samet Varol, Fred C Huang, Kristen L Buehne, Nicholas R Mayne, Isaac Weitzhandler, Mischa Bonn, Sapun H Parekh, Ashutosh Chilkoti
Post-translational modification of proteins is a strategy widely used in biological systems. It expands the diversity of the proteome and allows for tailoring of both the function and localization of proteins within cells as well as the material properties of structural proteins and matrices. Despite their ubiquity in biology, with a few exceptions, the potential of post-translational modifications in biomaterials synthesis has remained largely untapped. As a proof of concept to demonstrate the feasibility of creating a genetically encoded biohybrid material through post-translational modification, we report here the generation of a family of three stimulus-responsive hybrid materials-fatty-acid-modified elastin-like polypeptides-using a one-pot recombinant expression and post-translational lipidation methodology...
March 19, 2018: Nature Chemistry
Chayanid Ongpipattanakul, Satish Nair
Circular peptides have long been sought after as scaffolds for drug design as they demonstrate protein-like properties in the context of small, constrained peptides. Traditional routes towards the production of cyclic peptides rely on synthesis or semi-synthetic methods, which restrict their use as platforms for the production of large, structurally diverse chemical libraries. Here, we discuss the biosynthetic routes towards the N-C macrocyclization of linear peptide precursors, specifically, those transformations that are catalyzed by peptidases...
March 19, 2018: Biochemistry
Jianhua Ren, Yadwinder S Mann, Yuntao Zhang, Michael D Browne
Peptoids are sequence-controlled peptide-mimicking oligomers consisting of N-alkylated glycine units. Among many potential applications, peptoids have been thought of as a type of molecular information storage. Mass spectrometry analysis has been considered the method of choice for sequencing peptoids. Peptoids can be synthesized via solid phase chemistry using a repeating two-step reaction cycle. Here we present a method to manually synthesize oligo-peptoids and to analyze the sequence of the peptoids using tandem mass spectrometry (MS/MS) techniques...
February 21, 2018: Journal of Visualized Experiments: JoVE
E Ridolo, I Martignago, S Masieri
Allergic Rhinitis (AR) is an IgE-mediated hypersensitivity disease caused by inhalation of an allergen to which the patients is sensitized. Etiopathogenesis of AR comprises a sensitization phase, an immediate phase and a late phase. In the sensitization phase, inhaled allergens are processed in peptides and come into contact with the nasal mucosa cells. Antigen-Presenting Cells (APCs), especially represented by Dendritic Cells (DCs), capture them through the interaction with their own MHC class II complexes and migrate to lymph nodes...
January 2018: Journal of Biological Regulators and Homeostatic Agents
Jana Janssens, Yannick Vermeiren, Erik Fransen, Tony Aerts, Debby Van Dam, Sebastiaan Engelborghs, Peter P De Deyn
Introduction: Given the challenges concerning the differential diagnosis of dementia, we investigated the possible added value of monoaminergic compounds to the standard cerebrospinal fluid (CSF) Alzheimer's disease (AD) biomarkers. Particularly, regarding the AD versus dementia with Lewy bodies (DLB) comparison, monoamines or their metabolites might have added discriminative value as there is a more severe neuropathological burden in the locus coeruleus of DLB patients, the principal site of noradrenaline synthesis...
2018: Alzheimer's & Dementia: Diagnosis, Assessment & Disease Monitoring
Sandra C Vega, Diana A Martínez, María Del S Chalá, Hernán A Vargas, Jaiver E Rosas
Multidrug resistance of pathogenic bacteria has become a public health crisis that requires the urgent design of new antibacterial drugs such as antimicrobial peptides (AMPs). Seeking to obtain new, lactoferricin B (LfcinB)-based synthetic peptides as viable early-stage candidates for future development as AMPs against clinically relevant bacteria, we designed, synthesized and screened three new cationic peptides derived from bovine LfcinB. These peptides contain at least one RRWQWR motif and differ by the copy number (monomeric, dimeric or tetrameric) and structure (linear or branched) of this motif...
2018: Frontiers in Microbiology
Anouk S Lubbe, Qing Liu, Sanne J Smith, Jan Willem de Vries, Jos C M Kistemaker, Alex H De Vries, Ignacio Faustino, Zhuojun Meng, Wiktor Szymanski, Andreas Herrmann, Ben L Feringa
Reversible control over the functionality of biological systems via external triggers may be used in future medicine to reduce the need for invasive procedures. Additionally, externally regulated biomacromolecules are now considered as particularly attractive tools in nanoscience and the design of smart materials, due to their highly programmable nature and complex functionality. Incorporation of photoswitches into biomolecules, such as peptides, antibiotics and nucleic acids, has generated exciting results in the past few years...
March 18, 2018: Journal of the American Chemical Society
Guanyu Chen, Darren Svirskis, Weiyue Lu, Man Ying, Yuan Huang, Jingyuan Wen
Gemcitabine is a nucleoside analogue effective against a number of cancers. However, the full potential of this drug has not been realised, in part due to low oral bioavailability and frequent dosing requirements. This study reports the synthesis, in-vitro, ex-vivo and in-vivo evaluation of trimethyl chitosan (TMC) - CSKSSDYQC (CSK) peptide conjugates capable of enhancing the oral bioavailability of gemcitabine due to the ability to target intestinal goblet cells and promote intestinal cellular uptake. TMC was synthesized by a novel two-step methylation method to improve quanternization and yield...
March 13, 2018: Journal of Controlled Release: Official Journal of the Controlled Release Society
Andrzej T Slominski, Michal A Zmijewski, Przemyslaw M Plonka, Jerzy P Szaflarski, Ralf Paus
The skin, a self-regulating protective barrier organ, is empowered with sensory and computing capabilities to counteract the environmental stressors to maintain/restore disrupted cutaneous homeostasis. These complex functions are coordinated by a cutaneous neuro-endocrine system that also communicates in a bidirectional fashion with the central nervous, endocrine and immune systems, all acting in concert to control body homeostasis. While ultraviolet energy (UV) has played an important role in the origin and evolution of life, UV absorption by the skin not only triggers mechanisms that defend skin integrity and regulate global homeostasis, but also induces skin pathology (e...
March 12, 2018: Endocrinology
Maciej J Stawikowski, Gregg B Fields
A novel and convenient method for the synthesis of C -terminally branched collagen-model peptides has been achieved using tricine ( N -[tris(hydroxymethyl)methyl]glycine) as a branching scaffold and 1,2-diaminoethane or 1,4-diaminobutane as a linker. The peptide sequence was incorporated directly onto the linker and scaffold during solid-phase synthesis without additional manipulations. The resulting branched triple-helical peptides exhibited comparable thermal stabilities to the parent, unbranched sequence, and served as substrates for matrix metalloproteinase-1 (MMP-1)...
January 10, 2018: Tetrahedron Letters
Alejandro Amor-Coarasa, James Kelly, Shashikanth Ponnala, Yogindra Vedvyas, Anastasia Nikolopoulou, Clarence Williams, Moonsoo M Jin, J David Warren, John W Babich
INTRODUCTION: CXCR4 specific [18 F]-labeled positron emission tomography (PET) imaging agents are needed which would enable general distribution of the radiotracer for clinical investigation. We sought to synthesize, radiolabel and evaluate [18 F]RPS-544, a novel non-peptide CXCR4 antagonist as a CXCR4 specific probe. We compared [18 F]RPS-544 with the previously published [18 F]-3 ([18 F]RPS-510 in this paper) in a bi-lateral tumor model of differential CXCR4 expression for its ability to selectively target CXCR4 expression...
January 31, 2018: Nuclear Medicine and Biology
Dhivya Kumar, Rebecca T Thomason, Maya Yankova, Jonathan D Gitlin, Richard E Mains, Betty A Eipper, Stephen M King
The assembly of membranous extensions such as microvilli and cilia in polarized cells is a tightly regulated, yet poorly understood, process. Peptidylglycine α-amidating monooxygenase (PAM), a membrane enzyme essential for the synthesis of amidated bioactive peptides, was recently identified in motile and non-motile (primary) cilia and has an essential role in ciliogenesis in Chlamydomonas, Schmidtea and mouse. In mammalian cells, changes in PAM levels alter secretion and organization of the actin cytoskeleton...
March 14, 2018: Scientific Reports
Pernille Wismann, Søren L Pedersen, Gitte Hansen, Karin Mannerstedt, Philip J Pedersen, Palle B Jeppesen, Niels Vrang, Keld Fosgerau, Jacob Jelsing
AIM: Analogues of several gastrointestinal peptide hormones have been developed into effective medicines for treatment of diseases such as type 2 diabetes mellitus (T2DM), obesity and short bowel syndrome (SBS). In this study, we aimed to explore whether the combination of glucagon-like peptide-1 (GLP-1) and glucagon-like peptide-2 (GLP-2) into a potent co-agonist could provide additional benefits compared to existing monotherapies. METHODS: A short-acting (GUB09-123) and a half-life extended (GUB09-145) GLP-1/GLP-2 co-agonist were generated using solid-phase peptide synthesis and tested for effects on food intake, body weight, glucose homeostasis, and gut proliferation in lean mice and in diabetic db/db mice...
March 11, 2018: Physiology & Behavior
Hui Sun, Yuanxiu Hong, Yuejing Xi, Yijie Zou, Jingyi Gao, Jianzhong Du
Antimicrobial peptides (AMPs) have been attracting much attention due to their excellent antimicrobial efficiency and low rate in driving antimicrobial resistance (AMR) which has been increasing globally to alarming levels. Conjugation of AMPs into functional polymers not only preserves excellent antimicrobial activities but reduces the toxicity and offers more functionalities, which brings new insight towards developing multifunctional biomedical materials such as hydrogels, polymer vesicles, polymer micelles, etc...
March 14, 2018: Biomacromolecules
Mahboubeh Kheirabadi, Gardner S Creech, Jennifer X Qiao, David S Nirschl, David K Leahy, Kenneth M Boy, Percy H Carter, Martin D Eastgate
Macrocyclic peptides containing N-alkylated amino acids have emerged as a promising therapeutic modality, capable of modulating protein-protein interactions and intracellular delivery of hydrophilic payloads. While multi-channel automated Solid Phase Peptide Synthesis (SPPS) is a practical approach for peptide synthesis, the requirement for slow and inefficient chromatographic purification of the product peptides is a significant limitation to exploring these novel compounds. Herein, we invent a "catch-release" strategy for the non-chromatographic purification of macrocyclic peptides...
March 14, 2018: Journal of Organic Chemistry
Mahmoud Nasrollahzadeh, Mohaddeseh Sajjadi, Fatemeh Ghorbannezhad, S Mohammad Sajadi
A3 coupling is one of the few transition-metal catalyzed carbon-carbon bond forming reactions that have been established as a most direct, efficient and atom-economical synthetic approach to afford propargylamine derivatives using various catalysts. A large number of nanosized heterogeneous catalysts for three-component coupling reactions between an aldehyde, an amine, and a terminal alkyne have been popularly introduced as an A3 coupling in the last decade. The coupling product has found a broad application as a key intermediate for a variety of heterocyclic useful compounds and numerous biologically active molecules such as β-lactams, conformationally restricted peptides, isosteres, herbicides, fungicides, indolizines, pyrroles, quinolines and therapeutic drug molecules...
March 14, 2018: Chemical Record: An Official Publication of the Chemical Society of Japan ... [et Al.]
Susan E Hagen, Kun Liu, Yafei Jin, Lolita Piersimoni, Philip C Andrews, Hollis D Showalter
Two novel cyclic quaternary amine crosslinking probes are synthesized for structural mass spectrometry of protein complexes in solution and for analysis of protein interactions in organellar and whole cell extracts. Each exhibits high aqueous solubility, excellent protein crosslinking efficiencies, low collision induced dissociation (CID) energy fragmentation efficiencies, high stoichiometries of reaction, increased charges of crosslinked peptide ions, and maintenance of overall surface charge balance of crosslinked proteins...
March 14, 2018: Organic & Biomolecular Chemistry
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