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Peptide synthesis

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https://www.readbyqxmd.com/read/29351412/expression-of-ctgf-ccn2-in-response-to-lpa-is-stimulated-by-fibrotic-extracellular-matrix-via-the-integrin-fak-axis
#1
Camilo Riquelme-Guzman, Osvaldo Contreras, Enrique Brandan
Fibrosis is a common feature of several chronic diseases, and is characterized by exacerbated accumulation of extracellular matrix (ECM). Understanding the cellular and molecular mechanisms involved in the development of this condition is crucial for designing efficient treatments for those pathologies. Connective tissue growth factor (CTGF/CCN2) is a pleiotropic protein with strong pro-fibrotic activity. In this report, we present experimental evidence showing that ECM stimulates the synthesis of CTGF in response to lysophosphatidic acid (LPA)...
December 27, 2017: American Journal of Physiology. Cell Physiology
https://www.readbyqxmd.com/read/29348803/synthesis-of-a-chloroalkene-dipeptide-isostere-containing-peptidomimetic-and-its-biological-application
#2
Takuya Kobayakawa, Yudai Matsuzaki, Kentaro Hozumi, Wataru Nomura, Motoyoshi Nomizu, Hirokazu Tamamura
The first rapid and efficient chemical synthesis of a cyclic Arg-Gly-Asp (RGD) peptide containing a chloroalkene dipeptide isostere (CADI) is reported. By a developed synthetic method, an N-tert-butylsulfonyl protected CADI was obtained utilizing diastereoselective allylic alkylation as a key reaction. This CADI was also transformed into an N-Fmoc protected CADI in a few steps. The CADI was used in Fmoc-based solid-phase peptide synthesis. The first synthesis of a CADI-containing cyclic RGD peptide was successful, and the synthesized CADI-containing peptidomimetic was found to be a more potent inhibitor against integrin-mediated cell attachment than the parent cyclic peptide...
January 11, 2018: ACS Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/29345707/synthesis-and-characterization-of-a-photocleavable-collagen-like-peptide
#3
Alfredo Ornelas, Kaitlyn N Williams, Kevin A Hatch, Aurelio Paez, Angela C Aguilar, Cameron C Ellis, Nishat Tasnim, Supriyo Ray, Carl W Dirk, Thomas Boland, Binata Joddar, Chunqiang Li, Katja Michael
A 34-amino acid long collagen-like peptide rich in proline, hydroxyproline, and glycine, and with four photoreactive N-acyl-7-nitroindoline units incorporated into the peptide backbone was synthesized by on-resin fragment condensation. Its circular dichroism supports a stable triple helix structure. The built-in photochemical function enables the decomposition of the peptide into small peptide fragments by illumination with UV light of 350 nm in aqueous solution. Illumination of a thin film of the peptide, or a thin film of a photoreactive amino acid model compound containing a 5-bromo-7-nitroindoline moiety, with femtosecond laser light at 710 nm allows for the creation of well-resolved micropatterns...
January 18, 2018: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/29345421/synthesis-of-histidine-containing-oligopeptides-via-histidine-promoted-peptide-ligation
#4
Kai-Jin Huang, Yi-Chen Huang, Yuya Angel Lin
Histidine-containing peptides are valuable therapeutic agents for treatment of neurodegenerative diseases. However, the synthesis of histidine-containing peptides is not trivial due to the potential of imidazole sidechain of histidine to act as a nucleophile if unprotected. A peptide ligation method utilizing the imidazole sidechain of histidine has been developed. The key imidazolate intermediate that acts as an internal acyl transfer catalyst during ligation is generated by deprotonation. Transesterification with amino acids or peptides tethered with C-terminal thioester followed by N to N acyl shifts led to the final ligated products...
January 18, 2018: Chemistry, An Asian Journal
https://www.readbyqxmd.com/read/29345033/total-synthesis-and-conformational-study-of-the-anti-tubercular-cyclic-peptide-callyaerin-a-bearing-a-rare-rigidifying-z-2-3-diaminoacrylamide-moiety
#5
Margaret Anne Brimble, Shengping Zhang, Luis De Leon Rodriguez, Ivanhoe Leung, Greg Cook, Paul Harris
The first synthesis of the anti-TB cyclic peptide callyaerin A containing a rare (Z)-2,3-diaminoacrylamide bridging motif is reported. Fmoc-formylglycine-diethylacetal was used as a masked equivalent of formylglycine in the synthesis of the linear precursor of callyaerin A. Intramolecular cyclization between the formylglycine residue and the N-terminal amine in the linear peptide precursor afforded the macrocyclic natural product callyaerin A. Synthetic callyaerin A possessed potent anti-TB activity (MIC100 = 32 µM) while its all-amide congener was inactive...
January 18, 2018: Angewandte Chemie
https://www.readbyqxmd.com/read/29344085/synthesis-secretion-function-metabolism-and-application-of-natriuretic-peptides-in-heart-failure
#6
REVIEW
Shihui Fu, Ping Ping, Fengqi Wang, Leiming Luo
As a family of hormones with pleiotropic effects, natriuretic peptide (NP) system includes atrial NP (ANP), B-type NP (BNP), C-type NP (CNP), dendroaspis NP and urodilatin, with NP receptor-A (guanylate cyclase-A), NP receptor-B (guanylate cyclase-B) and NP receptor-C (clearance receptor). These peptides are genetically distinct, but structurally and functionally related for regulating circulatory homeostasis in vertebrates. In humans, ANP and BNP are encoded by NP precursor A (NPPA) and NPPB genes on chromosome 1, whereas CNP is encoded by NPPC on chromosome 2...
2018: Journal of Biological Engineering
https://www.readbyqxmd.com/read/29343792/prebiotic-formation-of-cyclic-dipeptides-under-potentially-early-earth-conditions
#7
Jianxi Ying, Rongcan Lin, Pengxiang Xu, Yile Wu, Yan Liu, Yufen Zhao
Cyclic dipeptides, also known as 2,5-diketopiperazines (DKPs), represent the simplest peptides that were first completely characterized. DKPs can catalyze the chiral selection of reactions and are considered as peptide precursors. The origin of biochemical chirality and synthesis of peptides remains abstruse problem believed to be essential precondition to origin of life. Therefore, it is reasonable to believe that the DKPs could have played a key role in the origin of life. How the formation of the DKPs through the condensation of unprotected amino acids in simulated prebiotic conditions has been unclear...
January 17, 2018: Scientific Reports
https://www.readbyqxmd.com/read/29342835/small-peptides-able-to-suppress-prostaglandin-e%C3%A2-generation-in-renal-mesangial-cells
#8
Sofia Vasilakaki, Oleksandr Pastukhov, Thomas Mavromoustakos, Andrea Huwiler, George Kokotos
Peptide drug discovery may play a key role in the identification of novel medicinal agents. Here, we present the development of novel small peptides able to suppress the production of PGE₂ in mesangial cells. The new compounds were generated by structural alterations applied on GK115, a novel inhibitor of secreted phospholipase A₂, which has been previously shown to reduce PGE₂ synthesis in rat renal mesangial cells. Among the synthesized compounds, the tripeptide derivative 11 exhibited a nice dose-dependent suppression of PGE₂ production, similar to that observed for GK115...
January 13, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/29341934/advances-in-the-delivery-of-antisense-oligonucleotides-for-combating-bacterial-infectious-diseases
#9
REVIEW
Xiao-Yan Xue, Xing-Gang Mao, Ying Zhou, Zhou Chen, Yue Hu, Zheng Hou, Ming-Kai Li, Jing-Ru Meng, Xiao-Xing Luo
Discovery and development of new antibacterial drugs against multidrug resistant bacterial strains have become more and more urgent. Antisense oligonucleotides (ASOs) show immense potential to control the spread of resistant microbes due to its high specificity of action, little risk to human gene expression, and easy design and synthesis to target any possible gene. However, efficient delivery of ASOs to their action sites with enough concentration remains a major obstacle, which greatly hampers their clinical application...
January 13, 2018: Nanomedicine: Nanotechnology, Biology, and Medicine
https://www.readbyqxmd.com/read/29341592/application-of-decafluorobiphenyl-dfbp-moiety-as-a-linker-in-bioconjugation
#10
Fernando Albericio, Saba Alapour, Beatriz G de la Torre, Deresh Ramjugernath, Neil Anthony Koorbanally
Considerable attention has been devoted to fluorinated compounds due to their unique and interesting properties. Many modern pharmaceuticals contain fluorinated substituents, which are commonly synthesized using selective fluorinating reagents. Decafluorobiphenyl (DFBP) as a fluorinated linker is susceptible to nucleophilic attack. This nucleophilic reaction has been widely studied using various nucleophiles. Sulfur and nitrogen containing nucleophiles have been of particular interest, especially in bioconjugated reactions...
January 17, 2018: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/29339755/a-prebiotic-template-directed-peptide-synthesis-based-on-amyloids
#11
Saroj K Rout, Michael P Friedmann, Roland Riek, Jason Greenwald
The prebiotic replication of information-coding molecules is a central problem concerning life's origins. Here, we report that amyloids composed of short peptides can direct the sequence-selective, regioselective and stereoselective condensation of amino acids. The addition of activated DL-arginine and DL-phenylalanine to the peptide RFRFR-NH2 in the presence of the complementary template peptide Ac-FEFEFEFE-NH2 yields the isotactic product FRFRFRFR-NH2, 1 of 64 possible triple addition products, under conditions in which the absence of template yields only single and double additions of mixed stereochemistry...
January 16, 2018: Nature Communications
https://www.readbyqxmd.com/read/29338907/new-photodynamic-molecular-beacons-pmb-as-potential-cancer-targeted-agents-in-pdt
#12
Aurélie Stallivieri, Ludovic Colombeau, Jérôme Devy, Nicolas Etique, Carine Chaintreuil, Bauyrzhan Myrzakhmetov, Mathilde Achard, Francis Baros, Philippe Arnoux, Régis Vanderesse, Céline Frochot
Further improvements in Photodynamic therapy (PDT) necessitate that the dye targets more selectively tumour tissues or neovascularization than healthy cells. Different enzymes such as matrix metalloproteinases (MMPs) are overexpressed in tumour areas. Among these MMPs, gelatinases (MMP-2 and MMP-9) and its activator MMP-14 are known to play a key role in tumour angiogenesis and the growth of many cancers such as glioblastoma multiforme (GBM), an aggressive malignant tumour of the brain. These last years, the concept of photodynamic molecular beacons (PMB) became interesting for controlling the photosensitizer's ability to generate singlet oxygen (1O2) close to target biomolecules as MMPs...
December 24, 2017: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/29338248/catalytic-oligopeptide-synthesis
#13
Zijian Liu, Hidetoshi Noda, Masakatsu Shibasaki, Naoya Kumagai
Waste-free catalytic assembly of α-amino acids is fueled by a multiboron catalyst that features a characteristic B3NO2 heterocycle, providing a versatile catalytic protocol wherein functionalized natural α-amino acid units are accommodated and commonly used protecting groups are tolerated. The facile dehydrative conditions eliminate the use of engineered peptide coupling reagents, exemplifying a greener catalytic alternative for peptide coupling. The catalysis is sufficiently robust to enable pentapeptide synthesis, constructing all four amide bond linkages in a catalytic fashion...
January 17, 2018: Organic Letters
https://www.readbyqxmd.com/read/29338205/control-of-amphiphile-self-assembly-via-bioinspired-metal-ion-coordination
#14
Abigail S Knight, Josefin Larsson, Jing M Ren, Raghida Bou Zerdan, Shay Seguin, Remy Vrahas, Jianfang Liu, Gang Ren, Craig J Hawker
Inspired by marine siderophores that exhibit a morphological shift upon metal coordination, hybrid peptide-polymer conjugates that assemble into different morphologies based on the nature of the metal ion coordination have been designed. Coupling of a peptide chelator, hexahistidine, with hydrophobic oligostyrene allows a modular strategy to be established for the efficient synthesis and purification of these tunable amphiphiles (oSt(His)6). Remarkably, in the presence of different divalent transition metal ions (Mn, Co, Ni, Cu, Zn, and Cd) a variety of morphologies were observed...
January 17, 2018: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/29338200/solid-phase-synthesis-of-oligopeptides-containing-sterically-hindered-amino-acids-on-non-swellable-resin-using-3-nitro-1-2-4-triazol-1-yl-tris-pyrrolidin-1-yl-phosphonium-hexafluorophosphate-pyntp-as-the-condensing-reagent
#15
Rintaro Iwata Hara, Yuta Mitsuhashi, Keita Saito, Yuske Maeda, Takeshi Wada
Peptides are still difficult to synthesize when they contain sterically hindered amino acids such as α,α-di-substituted amino acids and N-substituted amino acids. In this study, solid-phase syntheses of oligopeptides containing multiple α-aminoisobutyric acid (Aib) residues were performed in high yields by using a non-swellable resin as the solid-support and 3-nitro-1,2,4-triazol-1-yl-tris(pyrrolidin-1-yl)phosphonium hexafluorophosphate (PyNTP) as the condensing reagent.
January 17, 2018: ACS Combinatorial Science
https://www.readbyqxmd.com/read/29337569/total-synthesis-of-the-highly-n-methylated-acetylene-containing-anticancer-peptide-jahanyne
#16
Andrew Siow, George Opiyo, Iman Kavianinia, Freda F Li, Daniel P Furkert, Paul W R Harris, Margaret A Brimble
The first total synthesis of the highly N-methylated acetylene-containing lipopeptide jahanyne, an apoptosis-inducing natural product from marine cyanobacteria, is reported. A late-stage solution-phase coupling enabled introduction of the C-terminal ketone pyrrolidine moiety. A modified Fmoc solid-phase synthesis strategy was adopted to effectively couple multiple sterically hindered N-methylated amino acids while suppressing epimerization. The total synthesis has enabled confirmation of the proposed absolute configuration of natural jahanyne...
January 16, 2018: Organic Letters
https://www.readbyqxmd.com/read/29334413/features-of-auxiliaries-that-enable-native-chemical-ligation-beyond-glycine-and-cleavage-via-radical-fragmentation
#17
Simon Ferdinand Loibl, Andre Dallmann, Kathleen Hennig, Carmen Juds, Oliver Seitz
The native chemical ligation (NCL) is an invaluable tool in the total chemical synthesis of proteins. Ligation auxiliaries overcome the requirement for cysteine. However, the reported auxiliaries remained limited to glycine-containing ligation sites and the acidic conditions applied for cleavage of the typically applied N-benzyl-type linkages promote side reactions. With the aim to improve upon both ligation and cleavage, we systematically investigated alternative ligation scaffolds that challenge the N-benzyl dogma...
January 15, 2018: Chemistry: a European Journal
https://www.readbyqxmd.com/read/29331507/adropin-an-endocrine-link-between-the-biological-clock-and-cholesterol-homeostasis
#18
Sarbani Ghoshal, Joseph R Stevens, Cyrielle Billon, Clemence Girardet, Sadichha Sitaula, Arthur S Leon, D C Rao, James S Skinner, Tuomo Rankinen, Claude Bouchard, Marinelle V Nuñez, Kimber L Stanhope, Deborah A Howatt, Alan Daugherty, Jinsong Zhang, Matthew Schuelke, Edward P Weiss, Alisha R Coffey, Brian J Bennett, Praveen Sethupathy, Thomas P Burris, Peter J Havel, Andrew A Butler
OBJECTIVE: Identify determinants of plasma adropin concentrations, a secreted peptide translated from the Energy Homeostasis Associated (ENHO) gene linked to metabolic control and vascular function. METHODS: Associations between plasma adropin concentrations, demographics (sex, age, BMI) and circulating biomarkers of lipid and glucose metabolism were assessed in plasma obtained after an overnight fast in humans. The regulation of adropin expression was then assessed in silico, in cultured human cells, and in animal models...
December 30, 2017: Molecular Metabolism
https://www.readbyqxmd.com/read/29329073/nanobiostructure-of-fibrous-like-alumina-functionalized-with-an-analog-of-the-bp100-peptide-synthesis-characterization-and-biological-applications
#19
L M F C Torres, N A Braga, I P Gomes, M T Almeida, T L Santos, J P de Mesquita, L M da Silva, H R Martins, K C Kato, W T P Dos Santos, J M Resende, M C Pereira, M P Bemquerer, M A Rodrigues, R M Verly
The functionalization of alumina nanoparticles of specific morphology with antimicrobial peptides (AMP) can be a promising strategy for modeling medical devices and packaging materials for cosmetics, medicines or food, since the contamination by pathogens could be reduced. In this paper, we show the synthesis of a fibrous-like alumina nanobiostructure, as well as its functionalization with the peptide EAAA-BP100, an analog of the antimicrobial peptide BP100. The antibacterial activity of the obtained material against some bacterial strains is also investigated...
January 3, 2018: Colloids and Surfaces. B, Biointerfaces
https://www.readbyqxmd.com/read/29327924/two-step-macrocycle-synthesis-by-classical-ugi-reaction
#20
Eman M M Abdelraheem, Samad Khaksar, Katarzyna Kurpiewska, Justyna Kalinowska-Tłuścik, Shabnam Shaabani, Alexander Dömling
The direct non-peptidic macrocycle synthesis of α-isocyano-ω-amines via the classical Ugi 4-component reaction (U-4CR) is introduced. Herein, an efficient and flexible, just 2-step procedure to complex macrocycles is reported. In the first step, the reaction between unprotected diamines and isocyanocarboxylic acids gives high diversity of unprecedented building blocks in high yield. In the next step, the α-isocyano-ω-amines undergo an U-4CR with high diversity of aldehydes and carboxylic acids in a one-pot procedure...
January 12, 2018: Journal of Organic Chemistry
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