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Peptide synthesis

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https://www.readbyqxmd.com/read/28921941/the-lactococcus-lactis-kf147-nonribosomal-peptide-synthetase-polyketide-synthase-system-confers-resistance-to-oxidative-stress-during-growth-on-plant-leaf-tissue-lysate
#1
Benjamin L Golomb, Annabelle O Yu, Laurynne C Coates, Maria L Marco
Strains of Lactococcus lactis isolated from plant tissues possess adaptations that support their survival and growth in plant-associated microbial habitats. We previously demonstrated that genes coding for a hybrid nonribosomal peptide synthetase/polyketide synthase (NRPS/PKS) system involved in production of an uncharacterized secondary metabolite are specifically induced in L. lactis KF147 during growth on plant tissues. Notably, this NRPS/PKS has only been identified in plant-isolated strains of L. lactis...
September 18, 2017: MicrobiologyOpen
https://www.readbyqxmd.com/read/28915041/preorganized-cyclic-%C3%AE-%C3%AE-disubstituted-%C3%AE-amino-acids-bearing-functionalized-side-chains-that-act-as-peptide-helix-inducers
#2
Hiroyuki Kobayashi, Takashi Misawa, Kenji Matsuno, Yosuke Demizu
Preorganized cyclic α,α-disubstituted α-amino acids (dAA) bearing functionalized side chains that acted as peptide-helix inducers, which could be used for solid-phase peptide synthesis, were designed and synthesized. Furthermore, a helical octapeptide with the following amino acid sequence was prepared, and its preferred conformation was analyzed based on its CD spectra: Ac-X(1)EYSAX(2)KA-NH2 (11: X(1) = Api(C4N3), X(2) = Ac6c). The side-chain azido functional group of peptide 11 was efficiently converted to various 1,2,3-triazole groups via Huisgen 1,3-dipolar cycloaddition reactions involving different types of alkynes...
September 15, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28915003/the-evolution-of-dna-templated-synthesis-as-a-tool-for-materials-discovery
#3
Rachel K O'Reilly, Andrew J Turberfield, Thomas R Wilks
Precise control over reactivity and molecular structure is a fundamental goal of the chemical sciences. Billions of years of evolution by natural selection have resulted in chemical systems capable of information storage, self-replication, catalysis, capture and production of light, and even cognition. In all these cases, control over molecular structure is required to achieve a particular function: without structural control, function may be impaired, unpredictable, or impossible. The search for molecules with a desired function is often achieved by synthesizing a combinatorial library, which contains many or all possible combinations of a set of chemical building blocks (BBs), and then screening this library to identify "successful" structures...
September 15, 2017: Accounts of Chemical Research
https://www.readbyqxmd.com/read/28912890/glioma-dual-targeting-nanohybrid-protein-toxin-constructed-by-intein-mediated-site-specific-ligation-for-multistage-booster-delivery
#4
Yingzhi Chen, Meng Zhang, Hongyue Jin, Dongdong Li, Fan Xu, Aihua Wu, Jinyu Wang, Yongzhuo Huang
Malignant glioma is one of the most untreatable cancers because of the formidable blood-brain barrier (BBB), through which few therapeutics can penetrate and reach the tumors. Biologics have been booming in cancer therapy in the past two decades, but their application in brain tumor has long been ignored due to the impermeable nature of BBB against effective delivery of biologics. Indeed, it is a long unsolved problem for brain delivery of macromolecular drugs, which becomes the Holy Grail in medical and pharmaceutical sciences...
2017: Theranostics
https://www.readbyqxmd.com/read/28910148/bulk-scale-formulation-of-therapeutic-doses-of-clinical-grade-ready-to-use-177-lu-dota-tate-the-intricate-radiochemistry-aspects
#5
Anupam Mathur, Vrinda Prashant, Navin Sakhare, Sudipta Chakraborty, K V Vimalnath, Repaka Krishna Mohan, Chanda Arjun, Barkha Karkhanis, Ravi Seshan, Sandip Basu, Aruna Korde, Sharmila Banerjee, Ashutosh Dash, Satbir Singh Sachdev
INTRODUCTION: (177)Lu-DOTA-TATE is a clinically useful and promising therapeutic radiopharmaceutical for peptide receptor radionuclide therapy of neuroendocrine tumors (NETs) overexpressing somatostatin receptors. Currently, the radiopharmaceutical is prepared in-house at nuclear medicine centers, thereby restricting its use to limited centers only. In this article, the authors describe systematic studies toward bulk scale formulation of "ready-to-use" (177)Lu-DOTA-TATE using medium specific activity (177)Lu (740-1110 GBq/mg) at a centralized radiopharmacy facility...
September 2017: Cancer Biotherapy & Radiopharmaceuticals
https://www.readbyqxmd.com/read/28906041/total-synthesis-of-skyllamycins-a-c
#6
Richard James Payne, Andrew Giltrap, Jake Haeckl, Kenji Kurita, Roger Linington
The skyllamycins are a family of highly functionalized non-ribosomal cyclic depsipeptide natural products which contain the extremely rare α OH-glycine functionality. Herein we report the first total synthesis of skyllamycins A-C, together with the biofilm inhibitory activity of the natural products. Linear peptide precursors for each natural product were prepared through an efficient solid-phase route incorporating a number of synthetic modified amino acids. A novel macrocyclization step between a C-terminal amide and a N-terminal glyoxylamide moiety served as a key transformation to install the unique α OH-glycine unit and generate the natural products in the final step of the synthesis...
September 14, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/28905460/synthesis-of-acylborons-by-ozonolysis-of-alkenylboronates-preparation-of-an-enantioenriched-amino-acid-acylboronate
#7
Jumpei Taguchi, Toshiki Ikeda, Rina Takahashi, Ikuo Sasaki, Yasushi Ogasawara, Tohru Dairi, Naoya Kato, Yasunori Yamamoto, Jeffrey W Bode, Hajime Ito
A concise synthesis of acylborons was achieved by ozonolysis of alkenyl MIDA (N-methyliminodiacetic acid) boronates. This reaction exhibits excellent functional group tolerance and is applicable to various acyl MIDA boronates and potassium acyltrifluroborates (KATs) that could not be synthesized by previous methods. In addition, α-amino acylborons, which would be essential for peptide ligations, were prepared for the first time. The acylboron of L-alanine was obtained in high enantiopurity and found to be configurationally stable...
September 14, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/28905052/cyclic-peptide-production-using-a-macrocyclase-with-enhanced-substrate-promiscuity-and-relaxed-recognition-determinants
#8
Cristina N Alexandru-Crivac, Christian Umeobika, Niina Leikoski, Jouni Jokela, Kirstie A Rickaby, André M Grilo, Peter Sjö, Alleyn T Plowright, Mohannad Idress, Eike Siebs, Ada Nneoyi-Egbe, Matti Wahlsten, Kaarina Sivonen, Marcel Jaspars, Laurent Trembleau, David P Fewer, Wael E Houssen
Macrocyclic peptides have promising therapeutic potential but the scaling up of their chemical synthesis is challenging. The cyanobactin macrocyclase PatGmac is an efficient tool for production but is limited to substrates containing 6-11 amino acids and at least one thiazoline or proline. Here we report a new cyanobactin macrocyclase that can cyclize longer peptide substrates and those not containing proline/thiazoline and thus allows exploring a wider chemical diversity.
September 14, 2017: Chemical Communications: Chem Comm
https://www.readbyqxmd.com/read/28903058/insuperable-problems-of-the-genetic-code-initially-emerging-in-an-rna-world
#9
Peter R Wills, Charles W Carter
Differential equations for error-prone information transfer (template replication, transcription or translation) are developed in order to consider, within the theory of autocatalysis, the advent of coded protein synthesis. Variations of these equations furnish a basis for comparing the plausibility of contrasting scenarios for the emergence of specific tRNA aminoacylation, ultimately by enzymes, and the relationship of this process with the origin of the universal system of molecular biological information processing embodied in the Central Dogma...
September 10, 2017: Bio Systems
https://www.readbyqxmd.com/read/28902490/direct-intra-nuclear-anticancer-drug-delivery-via-polydimethylsiloxane-nanoparticles-in-vitro-and-in-vivo-xenograft-studies
#10
Gargi Mishra, Souryadeep Bhattacharyya, Vipul Bhatia, Bushra Ateeq, Ashutosh Sharma, Sri Sivakumar
Direct delivery of anticancer drugs to nuclei of tumor cells is required to enhance the therapeutic activity which can be achieved by a nuclear localization signal (NLS) or peptide-decorated nano-vehicles. However, NLS/peptide-based approaches may create certain undesirable immunological responses and the utilized synthesis processes are generally labor intensive. To this end, we report ligand-free, enhanced intra-nuclear delivery of Doxorubicin (Dox) to different cancer cells via porous polydimethylsiloxane (PDMS) nanoparticles (NPs)...
September 13, 2017: ACS Applied Materials & Interfaces
https://www.readbyqxmd.com/read/28902151/apetx4-a-novel-sea-anemone-toxin-and-a-modulator-of-the-cancer-relevant-potassium-channel-kv10-1
#11
Lien Moreels, Steve Peigneur, Diogo T Galan, Edwin De Pauw, Lászlo Béress, Etienne Waelkens, Luis A Pardo, Loïc Quinton, Jan Tytgat
The human ether-à-go-go channel (hEag1 or KV10.1) is a cancer-relevant voltage-gated potassium channel that is overexpressed in a majority of human tumors. Peptides that are able to selectively inhibit this channel can be lead compounds in the search for new anticancer drugs. Here, we report the activity-guided purification and electrophysiological characterization of a novel KV10.1 inhibitor from the sea anemone Anthopleura elegantissima. Purified sea anemone fractions were screened for inhibitory activity on KV10...
September 13, 2017: Marine Drugs
https://www.readbyqxmd.com/read/28901187/peptide-modified-chitosan-hydrogels-accelerate-skin-wound-healing-by-promoting-fibroblast-proliferation-migration-and-secretion
#12
Xionglin Chen, Min Zhang, Shixuan Chen, Xueer Wang, Zhihui Tian, Yinghua Chen, Pengcheng Xu, Lei Zhang, Lu Zhang, Lin Zhang
Skin wound healing is a complicated process that involves a variety of cells and cytokines. Fibroblasts play an important role in this process and participate in transformation into myofibroblasts, the synthesis of extracellular matrix (ECM) and fibers, and the secretion of a variety of growth factors. This study assessed the effects of peptide Ser-Ile-Lys-Val-Ala-Val (SIKVAV)--modified chitosan hydrogels on skin wound healing. We investigated the capability of peptide SIKVAV to promote cell proliferation and migration, the synthesis of collagen, and the secretion of a variety of growth factors using fibroblasts in vitro...
August 2017: Cell Transplantation
https://www.readbyqxmd.com/read/28900516/sensitive-in-vivo-visualization-of-breast-cancer-using-ratiometric-protease-activatable-fluorescent-imaging-agent-avb-620
#13
Marcel Miampamba, Junjie Liu, Alec Harootunian, Andrew J Gale, Stephen Baird, Steven L Chen, Quyen T Nguyen, Roger Y Tsien, Jesús E González
With the goal of improving intraoperative cancer visualization, we have developed AVB-620, a novel intravenously administered, in vivo fluorescent peptide dye conjugate that highlights malignant tissue and is optimized for human use. Matrix metalloproteinases (MMPs) hydrolyze AVB-620 triggering tissue retention and a ratiometric fluorescence color change which is visualized using camera systems capable of imaging fluorescence and white light simultaneously. AVB-620 imaging visualizes primary tumors and demonstrated high in vivo diagnostic sensitivity and specificity (both >95%) for identifying breast cancer metastases to lymph nodes in two immunocompetent syngeneic mouse models...
2017: Theranostics
https://www.readbyqxmd.com/read/28900018/distinct-spatiotemporal-dynamics-of-peptidoglycan-synthesis-between-mycobacterium%C3%A2-smegmatis-and-mycobacterium%C3%A2-tuberculosis
#14
Helene Botella, Guangli Yang, Ouathek Ouerfelli, Sabine Ehrt, Carl F Nathan, Julien Vaubourgeix
Peptidoglycan (PG), a polymer cross-linked by d-amino acid-containing peptides, is an essential component of the bacterial cell wall. We found that a fluorescent d-alanine analog (FDAA) incorporates chiefly at one of the two poles in Mycobacterium smegmatis but that polar dominance varies as a function of the cell cycle in Mycobacterium tuberculosis: immediately after cytokinesis, FDAAs are incorporated chiefly at one of the two poles, but just before cytokinesis, FDAAs are incorporated comparably at both. These observations suggest that mycobacterial PG-synthesizing enzymes are localized in functional compartments at the poles and septum and that the capacity for PG synthesis matures at the new pole in M...
September 12, 2017: MBio
https://www.readbyqxmd.com/read/28899090/synthesis-and-sensory-characteristics-of-kokumi-%C3%AE-glu-n-phe-in-the-presence-of-glutamine-and-phenylalanine-glutaminase-from-bacillus-amyloliquefaciens-or-aspergillus-oryzae-as-the-catalyst
#15
Juan Yang, Dongxiao Sun-Waterhouse, Chun Cui, Keming Dong, Wei Wang
The transpeptidase activity of glutaminase from Bacillus amyloliquefaciens (GBA) and Aspergillus oryzae (GAO) to yield γ-[Glu]n-Phe peptides were verified for the first time. In the presence of Gln and Phe, γ-Glu-Phe and γ-Glu-γ-Glu-Phe were synthesized by GAO, and γ-Glu-Phe, γ-Glu-γ-Glu-Phe, γ-Glu-γ-Glu-γ-Glu-Phe, γ-Glu-γ-Glu-γ-Glu-γ-Glu-Phe and γ-Glu-γ-Glu-γ-Glu-γ-Glu-γ-Glu-Phe were synthesized by GBA. The Km values for the transpeptidation catalysed by GBA and GAO were 47.88 and 153.92 mM (Phe as the acceptor), 84...
September 13, 2017: Journal of Agricultural and Food Chemistry
https://www.readbyqxmd.com/read/28898054/synthesis-radiolabeling-and-characterization-of-plasma-protein-binding-ligands-potential-tools-for-modulation-of-the-pharmacokinetic-properties-of-radio-pharmaceuticals
#16
Cristina Müller, Renáta Farkas, Francesca Borgna, Raffaella M Schmid, Martina Benešová, Roger Schibli
The development of (radio)pharmaceuticals with favorable pharmacokinetic profiles is crucial for allowing the optimization of the imaging or therapeutic potential and the minimization of undesired side effects. The aim of this study was, therefore, to evaluate and compare three different plasma protein binders (PPB-01, PPB-02, and PPB-03) that are potentially useful in combination with (radio)pharmaceuticals to enhance their half-life in the blood. The entities were functionalized with a 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA) chelator via a l-lysine and β-alanine linker moiety using solid-phase peptide chemistry and labeled with (177)Lu (T1/2 = 6...
September 12, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28894917/identification-and-characterization-of-the-ficellomycin-biosynthesis-gene-cluster-from-streptomyces-ficellus
#17
Yang Liu, Meng Li, Huiyan Mu, Shuting Song, Ying Zhang, Kun Chen, Xihong He, Haikuan Wang, Yujie Dai, Fuping Lu, Zhongli Yan, Huitu Zhang
Ficellomycin is a peptide-like antibiotic which exhibits potent in vitro activity against Penicillium oxalicum and Staphylococcus aureus, even against strains resistant to most clinically used antibiotics. The gene cluster responsible for ficellomycin biosynthesis was cloned from Streptomyces ficellus and sequenced. It was found to contain 26 ORFs and is located within 30 kb of contiguous DNA. Targeted disruption of the encoding genes revealed that most were involved in the functional section of ficellomycin biosynthesis, such as peptide assembly, regulation, resistance, and biosynthesis of the precursor of ficellomycin 2-[4-guanidyl-1-azabicyclo[3...
September 11, 2017: Applied Microbiology and Biotechnology
https://www.readbyqxmd.com/read/28894900/interaction-between-luteinizing-hormone-releasing-hormone-and-gm1-doped-cholesterol-sphingomyelin-vesicles-a-spectroscopic-study
#18
Zarrin Shahzadi, Chaitali Mukhopadhyay
Understanding the role of neural membrane in translocation and action of neurohormone is of great importance. Luteinizing hormone-releasing hormone (LHRH) is a neuropeptide hormone and it acts as a final signaling molecule by stimulating the synthesis of LH and FSH to maintain reproduction in all vertebrates. The receptors of LHRH are found in breast tumors and pituitary gland in the brain. Moreover, neural plasma membrane is also found to contain specific binding site for LHRH. The mechanism by which LHRH binds to membrane before it binds to the receptors is a very critical step and can have a profound impact upon the translation of peptide across the membrane...
September 11, 2017: Journal of Membrane Biology
https://www.readbyqxmd.com/read/28893064/aqueous-raft-synthesis-of-glycopolymers-for-determination-of-saccharide-structure-and-concentration-effects-on-amyloid-%C3%AE-aggregation
#19
Pradipta Kumar Das, Dexter N Dean, April L Fogel, Fei Liu, Brooks A Abel, Charles L McCormick, Eugenia Kharlampieva, Vijayaraghavan Rangachari, Sarah E Morgan
GM1 ganglioside is known to promote amyloid-β (Aβ) peptide aggregation in Alzheimer's disease. The roles of the individual saccharides and their distribution in this process are not understood. Acrylamide-based glycomonomers with either β-D-glucose or β-D-galactose pendant groups were synthesized to mimic the stereochemistry of saccharides present in GM1 and characterized via 1H NMR and electrospray ionization mass spectrometry. Glycopolymers of different molecular weights were synthesized by aqueous reversible addition fragmentation chain transfer (aRAFT) polymerization and characterized by NMR and GPC...
September 11, 2017: Biomacromolecules
https://www.readbyqxmd.com/read/28892365/recent-developments-in-antimicrobial-peptide-conjugated-gold-nanoparticles
#20
Urawadee Rajchakit, Vijayalekshmi Sarojini
The escalation of multidrug-resistant pathogens has created a dire need to develop novel ways of addressing this global therapeutic challenge. Because of their antimicrobial activities, combination of antimicrobial peptides (AMPs) and nanoparticles is a promising tool to kill drug resistant pathogens. In recent years, several studies using AMP-nanoparticle conjugates, especially metallic nanoparticles, as potential antimicrobial agents against drug resistant pathogens have been published. Amongst these, antimicrobial peptide conjugated gold nanoparticles (AMP-AuNPs) are particularly attractive because of the non-toxic nature of gold and the possibility of fine tuning the AMP-NP conjugation chemistry...
September 11, 2017: Bioconjugate Chemistry
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