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Peptide synthesis

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https://www.readbyqxmd.com/read/28532072/new-bioactive-bone-like-microspheres-with-intrinsic-magnetic-properties-obtained-by-bio-inspired-mineralisation-process
#1
Tatiana Marisa Fernandes Patrício, Silvia Panseri, Monica Sandri, Anna Tampieri, Simone Sprio
A bio-inspired mineralisation process was investigated and applied to develop novel hybrid magnetic materials by heterogeneous nucleation of Fe(2+)/Fe(3+)-doped hydroxyapatite nanocrystals onto a biopolymeric matrix made of a Type I collagen-based recombinant peptide (RCP). The effect of the synthesis temperature on the phase composition, crystallinity and magnetic properties of the nucleated inorganic phase was studied. The as-obtained magnetic materials were then engineered, by using a water-in-oil emulsification process, into hybrid magnetic microspheres, which were stabilized by de-hydrothermal treatment yielding cross-linking of the macromolecular matrix...
August 1, 2017: Materials Science & Engineering. C, Materials for Biological Applications
https://www.readbyqxmd.com/read/28531986/biomimicking-synthesis-of-photoluminescent-molecular-lantern-catalyzed-by-in-situ-formation-of-nanogold-catalysts
#2
Yong Yu, Xin Ting Zheng, Boon Wei Yee, Yen Nee Tan
Bioluminescence has been widely recognized as a powerful imaging tool for biological investigations. Synthesis of molecular lanterns that mimic bioluminescence in nature is of great interest. Herein we report a synthesis of molecular lantern by utilizing the catalytic properties of ultrasmall (<2nm) gold nanoclusters (AuNC), which is inspired by the enzymatic light-up of luciferin in the biological system. Small molecules such as hydroquinone and Cys-Gly peptides are used to direct the synthesis of AuNC via a biotemplating approach, while the in-situ formation of AuNC simultaneously catalyze the formation of luciferin-like, brightly fluorescent dye (λem=520nm, QY=0...
August 1, 2017: Materials Science & Engineering. C, Materials for Biological Applications
https://www.readbyqxmd.com/read/28530745/self-assembling-peptide-and-protein-amyloids-from-structure-to-tailored-function-in-nanotechnology
#3
REVIEW
Gang Wei, Zhiqiang Su, Nicholas P Reynolds, Paolo Arosio, Ian W Hamley, Ehud Gazit, Raffaele Mezzenga
Self-assembled peptide and protein amyloid nanostructures have traditionally been considered only as pathological aggregates implicated in human neurodegenerative diseases. In more recent times, these nanostructures have found interesting applications as advanced materials in biomedicine, tissue engineering, renewable energy, environmental science, nanotechnology and material science, to name only a few fields. In all these applications, the final function depends on: (i) the specific mechanisms of protein aggregation, (ii) the hierarchical structure of the protein and peptide amyloids from the atomistic to mesoscopic length scales and (iii) the physical properties of the amyloids in the context of their surrounding environment (biological or artificial)...
May 22, 2017: Chemical Society Reviews
https://www.readbyqxmd.com/read/28530742/a-survey-of-the-different-roles-of-polyoxometalates-in-their-interaction-with-amino-acids-peptides-and-proteins
#4
Mina Arefian, Masoud Mirzaei, Hossein Eshtiagh-Hosseini, Antonio Frontera
One of the most attractive areas in inorganic chemistry is the synthesis of polyoxometalates (POMs) exhibiting new properties and applications. Since the impact of POMs in biochemistry and related fields of research has increased in the last few years, there has been a special interest in this topic. Significant progress in biological applications has been made where the interaction of POMs with amino acids, peptides and proteins is relevant. Versatile POMs play a series of different roles in the interaction with these biomolecules as described in this review...
May 22, 2017: Dalton Transactions: An International Journal of Inorganic Chemistry
https://www.readbyqxmd.com/read/28530544/the-second-generation-of-highly-potent-hepatitis-c-virus-hcv-ns3-4a-protease-inhibitors-evolutionary-design-based-on-tailor-made-amino-acids-synthesis-and-major-features-of-bio-activity
#5
Shuni Wang, Yibing Wang, Jiang Wang, Tatsunori Sato, Kunisuke Izawa, Vadim A Soloshonok, Hong Liu
Hepatitis C is a current pandemic liver disease caused by the hepatitis C virus (HCV) with high morbidity and mortality. Recently, the direct-acting antiviral agents (DAAs) targeting HCV NS3/4A, NS5A and NS5B have become the most effective therapies against HCV infection in the clinical treatment. Among them, the second-generation of NS3/4A inhibitors have emerged as the mainstay of the DAA therapies, which are derived from the peptide substrate of NS3/4A protease and modified with various tailor-made amino acids in order to achieve high sustained virologic response (SVR) against HCV...
May 22, 2017: Current Pharmaceutical Design
https://www.readbyqxmd.com/read/28530391/single-bead-quantification-of-peptide-loading-distribution-for-one-bead-one-compound-library-synthesis-using-confocal-raman-spectroscopy
#6
Yuchen Tang, Yann Thillier, Ruiwu Liu, Xiaocen Li, Kit S Lam, Tingjuan Gao
We report an analytical method to determine peptide loading of "one-bead one-compound" (OBOC) combinatorial peptide libraries at single-bead level. The quantification is based on a linear relationship between the amount of N-terminal amino groups on individual peptide beads and the intensity of Raman signal obtained from a specifically designed reporter labeled on amino groups. Confocal Raman spectroscopy was employed to characterize peptide loading of beads with defined peptide sequences and from OBOC combinatorial peptide libraries...
May 22, 2017: Analytical Chemistry
https://www.readbyqxmd.com/read/28529634/novel-linear-peptides-with-high-affinity-to-%C3%AE-v%C3%AE-3-integrin-for-precise-tumor-identification
#7
Yi Ma, Guanhua Ai, Congying Zhang, Menglu Zhao, Xue Dong, Zhihao Han, Zhaohui Wang, Min Zhang, Yuxi Liu, Weidong Gao, Siwen Li, Yueqing Gu
Development of alternative linear peptides for targeting αvβ3 integrin has attracted much attention, as the traditional peptide ligand, cyclic RGD, is limited by inferior water-solubility and complex synthesis. Using pharmacophore-based virtual screening and high-throughput molecular docking, we identified two novel linear small peptides RWr and RWrNM with high affinity and specificity to αvβ3 integrin. The competitive binding with cyclic RGD (c(RGDyK)) and cellular uptake related to the integrin expression levels verified their affinity to αvβ3 integrin...
2017: Theranostics
https://www.readbyqxmd.com/read/28527999/nanocellulose-collagen-apatite-composite-associated-with-osteogenic-growth-peptide-bone-regeneration
#8
Sybele Saska, Lucas Novaes Teixeira, Larissa Moreira Spinola de Castro Raucci, Raquel Mantuaneli Scarel-Caminaga, Leonardo Pereira Franchi, Raquel Alves Dos Santos, Silvia Helena Santagneli, Marisa Veiga Capela, Paulo Tambasco de Oliveira, Catarina Satie Takahashi, Ana Maria Minarelli Gaspar, Younès Messaddeq, Sidney José Lima Ribeiro, Reinaldo Marchetto
Despite advances in the field of biomaterials for bone repair/regeneration, some challenges for developing an ideal bone substitute need to be overcome. Herein, this study synthesized and evaluated in vitro a nanocomposite based on bacterial cellulose (BC), collagen (COL), apatite (Ap) and osteogenic growth peptide (OGP) or its C-terminal pentapeptide [OGP(10-14)] for bone regeneration purposes. The BC-COL nanocomposites were successfully obtained by carbodiimide-mediated coupling as demonstrated by spectroscopy analysis...
May 17, 2017: International Journal of Biological Macromolecules
https://www.readbyqxmd.com/read/28526476/revisiting-ligation-at-selenomethionine-insights-into-native-chemical-ligation-at-selenocysteine-and-homoselenocysteine
#9
Rebecca Notis Dardashti, Norman Metanis
Selenomethionine (Sem) has been incorporated recombinantly into proteins many times to elucidate their structure and function. In this paper, we revisit incorporation via chemical protein synthesis to shed light on the mechanism of native chemical ligation. The effect of chalcogen position on ligation is investigated, and selenium-containing peptide ligation is optimized. Additionally, selective methylation is performed on selenolates in a peptide in the presence of unprotected thiols.
May 5, 2017: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/28526268/structural-and-functional-aspects-of-the-nonribosomal-peptide-synthetase-condensation-domain-superfamily-discovery-dissection-and-diversity
#10
REVIEW
Kristjan Bloudoff, T Martin Schmeing
Nonribosomal peptide synthetases (NRPSs) are incredible macromolecular machines that produce a wide range of biologically- and therapeutically-relevant molecules. During synthesis, peptide elongation is performed by the condensation (C) domain, as it catalyzes amide bond formation between the nascent peptide and the amino acid it adds to the chain. Since their discovery more than two decades ago, C domains have been subject to extensive biochemical, bioinformatic, mutagenic, and structural analyses. They are composed of two lobes each with homology to chloramphenicol acetyltransferase, have two binding sites for their two peptidyl carrier protein-bound ligands, and have an active site with conserved motif HHxxxDG located between the two lobes...
May 16, 2017: Biochimica et Biophysica Acta
https://www.readbyqxmd.com/read/28526016/efficient-extracellular-recombinant-production-and-purification-of-a-bacillus-cyclodextrin-glucanotransferase-in-escherichia-coli
#11
Christian Sonnendecker, Ren Wei, Elisabeth Kurze, Jinpeng Wang, Thorsten Oeser, Wolfgang Zimmermann
BACKGROUND: Cyclodextrin glucanotransferases (CGTases) catalyze the synthesis of cyclodextrins, cyclic oligosaccharides composed of glucose monomers that find applications in the pharmaceutical, food, and cosmetic industries. An economic application of these industrially important enzymes requires their efficient production and recovery. In this study, the effect of Sec-type signal peptides on the recombinant expression of a CGTase derived from Bacillus sp. G825-6 was investigated in Escherichia coli BL21(DE3) using a codon-adapted gene...
May 19, 2017: Microbial Cell Factories
https://www.readbyqxmd.com/read/28524918/urotensin-ii-peptidomimetic-incorporating-a-non-reducible-1-5-triazole-disulfide-bond-reveals-a-pseudo-irreversible-covalent-binding-mechanism-to-the-urotensin-g-protein-coupled-receptor
#12
Salvatore Pacifico, Aidan Kerckhoffs, Andrew J Fallow, Rachel E Foreman, Remo Guerrini, John McDonald, David G Lambert, Andrew G Jamieson
The urotensin-II receptor (UTR) is a class A GPCR that predominantly binds to the pleiotropic cyclic peptide urotensin-II (U-II). U-II is constrained by a disulfide bridge that induces a β-turn structure and binds pseudo-irreversibly to UTR and is believed to result in a structural rearrangement of the receptor. However, it is not well understood how U-II binds pseudo-irreversibly and the nature of the reorganization of the receptor that results in G-protein activation. Here we describe a series of U-II peptidomimetics incorporating a non-reducible disulfide bond structural surrogate to investigate the feasibility that native U-II binds to the G protein-coupled receptor through disulfide bond shuffling as a mechanism of covalent interaction...
May 19, 2017: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/28524364/biofunctional-microgel-based-fertilizers-for-controlled-foliar-delivery-of-nutrients-to-plants
#13
Richard A Meurer, Steffen Kemper, Sandra Knopp, Thomas Eichert, Felix Jakob, Heiner E Goldbach, Ulrich Schwaneberg, Andrij Pich
Foliar application of micronutrients (e.g. Fe(3+) ) onto plants over an extended time is challenging and often not possible due to insufficient rainfastness. Smart delivery systems which enable micronutrient release over several weeks would offer innovative and sustainable options to improve plant health and food production. Herein, we report a novel foliar fertilizer delivery system based on functional pH-responsive biohybrid microgels that have orthogonal functionality as carriers of micronutrients and employ peptides (termed anchor peptides) as foliar adhesion promoters...
May 19, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/28524273/synthesis-and-biological-evaluation-of-novel-peptides-based-on-antimicrobial-peptides-as-potential-agents-with-anti-tumor-and-multidrug-resistance-reversing-activities
#14
Bo Zhang, Wei Shi, Jieming Li, Chen Liao, Limei Yang, Wenlong Huang, Hai Qian
Tumor chemotherapy, which plays an important role in the clinical treatment of metastatic cancer, is limited by low selectivity and drug resistance in clinical application. In our study, we selected antimicrobial peptide BP100 as a lead peptide, designed and synthesized a series of novel antineoplastic peptides through solid-phase synthesis. Amongst them, B4 and B8 showed excellent anti-cancer activity. As revealed by further investigations, these peptides could disrupt the cell membrane, trigger the cytochrome C release into cytoplasm and ultimately lead to apoptosis...
May 19, 2017: Chemical Biology & Drug Design
https://www.readbyqxmd.com/read/28523604/chemo-enzymatic-synthesis-of-a-glycosylated-peptide-containing-a-complex-n-glycan-based-on-unprotected-oligosaccharides-by-using-dmt-mm-and-endo-m
#15
Yusuke Tomabechi, Toshihiko Katoh, Munetaka Kunishima, Toshiyuki Inazu, Kenji Yamamoto
For chemo-enzymatic synthesis of a glycosylated peptide, 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) was used for the synthesis of a N-acetylglucosaminyl peptide and a pseudoglycopeptide by solid-phase peptide synthesis without the requirement of protecting groups on the carbohydrate. We also performed transglycosylation of an N-glycan to the N-acetylglucosaminyl peptide using endo-β-N-acetylglucosaminidase from Mucor hiemalis (Endo-M) to synthesize a glycopeptide containing a complex N-glycan...
May 18, 2017: Glycoconjugate Journal
https://www.readbyqxmd.com/read/28523379/novel-dna-rna-targeting-amino-acid-beacon-for-the-versatile-incorporation-at-any-position-within-the-peptide-backbone
#16
Tamara Šmidlehner, Ivo Piantanida
One-pot tandem synthesis was for the first time applied to attach fluorophore to the amino acid side chain, yielding amino acid ready for peptide coupling at the N-terminus, and also upon activation at the C-terminus. Two new compounds differing only in fluorophore-linker length showed exceptional fluorimetric and CD recognition between DS-RNA and DS-DNA, thus being promising beacons for versatile peptide incorporation.
May 18, 2017: Amino Acids
https://www.readbyqxmd.com/read/28522421/a-chymotrypsin-like-serine-protease-from-portunus-trituberculatus-involved-in-pathogen-recognition-and-amp-synthesis-but-not-required-for-prophenoloxidase-activation
#17
Hourong Liu, Yuan Liu, Chengwen Song, Zhaoxia Cui
Clip domain serine proteases (clip-SPs) play critical roles in various immune responses in arthropods, such as hemolymph coagulation, antimicrobial peptide (AMP) synthesis, cell adhesion and melanization. In the present study, we report the molecular and functional characterization of a clip domain serine protease (PtcSP2) from the swimming crab Portunus trituberculatus. The N-terminal clip domain and the C-terminal SP-like domain of PtcSP2 were expressed in Escherichia coli system, and assayed for their activities...
May 15, 2017: Fish & Shellfish Immunology
https://www.readbyqxmd.com/read/28520410/proteolytically-stable-cyclic-decapeptide-for-breast-cancer-cell-targeting
#18
Yogita Raghuwanshi, Hashem Rajab Etayash, Rania Soudy, Igor Paiva, Afsaneh Lavasanifar, Kamaljit Kaur
Starting with a previously reported linear breast cancer targeting decapeptide WxEAAYQkFL, here we report the synthesis of a novel cyclic peptide analogue cyclicWXEAAYQkFL. The N- to C-terminus amide cyclized peptide with one D-amino acid (k) displayed higher uptake by breast cancer cells, with minimal uptake by the non-cancerous cells compared to the linear peptide with two D-amino acids (x and k), and was stable toward proteolytic degradation. When immobilized on gold microcantilever surface, the cyclic peptide was able to capture breast cancer cells specifically and sense samples with ≥25 cancer cells/mL...
May 18, 2017: Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28518069/modification-and-functionalization-of-the-guanidine-group-by-tailor-made-precursors
#19
Tobias G Kapp, Maximilian Fottner, Horst Kessler
The guanidine group is one of the most important pharmacophoric groups in medicinal chemistry. The only amino acid carrying a guanidine group is arginine. In this article, an easy method for the modification of the guanidine group in peptidic ligands is provided, with an example of RGD-binding integrin ligands. It was recently demonstrated that the distinct modification of the guanidine group in these ligands allows for the selective modulation of the subtype (e.g., between the subtypes αv and α5). Moreover, a formerly unknown strategy for the functionalization via the guanidine group was demonstrated, and the synthetic approach is reviewed in this document...
April 27, 2017: Journal of Visualized Experiments: JoVE
https://www.readbyqxmd.com/read/28517015/genetic-incorporation-of-4-fluorohistidine-into-peptides-enables-selective-affinity-purification
#20
Christine M Ring, Emil S Iqbal, David E Hacker, Matthew C T Hartman, T Ashton Cropp
Due to the lowered pKa of 4-fluorohistidine relative to histidine, peptides and proteins containing this amino acid are potentially endowed with novel properties. We report here the optimized synthesis of 4-fluorohistidine and show that it can efficiently replace histidine in in vitro translation reactions. Moreover, peptides containing 6×-fluorohistidine tags are able to be selectively captured and eluted from nickel resin in the presence of his-tagged protein mixtures.
May 18, 2017: Organic & Biomolecular Chemistry
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