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Peptide synthesis

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https://www.readbyqxmd.com/read/28805740/adp-ribosyl-n%C3%A2-a-versatile-precursor-for-divergent-syntheses-of-adp-ribosylated-compounds
#1
Lingjun Li, Qianqian Li, Shengqiang Ding, Pengyang Xin, Yuqin Zhang, Shenlong Huang, Guisheng Zhang
Adenosine diphosphate-ribose (ADP-ribose) and its derivatives play important roles in a series of complex physiological procedures. The design and synthesis of artificial ADP-ribosylated compounds is an efficient way to develop valuable chemical biology tools and discover new drug candidates. However, the synthesis of ADP-ribosylated compounds is currently difficult due to structural complexity, easily broken pyrophosphate bond and high hydrophilicity. In this paper, ADP-ribosyl-N₃ was designed and synthesized for the first time...
August 14, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28805368/pyrophosphate-recognition-and-sensing-in-water-using-bis-zinc-ii-dipicolylamino-functionalized-peptides
#2
Katrina A Jolliffe
Phosphate oxoanions and phosphorylated biomolecules (such as nucleotides, lipids, and proteins) play key roles in a wide range of biological processes. The ability to selectively detect these ions in the presence of each other has numerous applications in biochemistry and biomedicine. However, receptors and sensors that can discriminate between polyphosphate species with high selectivity and in biologically relevant conditions are rare. In this Account, we show how peptides (both cyclic and linear) can be used to position two zinc(II)dipicolylamine [Zn(II)DPA] binding sites in an appropriate arrangement to provide selective binding of pyrophosphate (PPi) in the presence of other polyphosphate species, including ATP, and in complex media such as cell growth buffer...
August 14, 2017: Accounts of Chemical Research
https://www.readbyqxmd.com/read/28803471/altering-the-peptide-binding-selectivity-of-polymeric-reverse-micelle-assemblies-via-metal-ion-loading
#3
Meizhe Wang, Bo Zhao, Jingjing Gao, Huan He, Laura J Castellanos, Sankaran Thayumanavan, Richard W Vachet
Supramolecular reverse micelle assemblies, formed by amphiphilic copolymers, can selectively encapsulate molecules in their interiors depending on the functional groups present in the polymers. Altering the binding selectivity of these materials typically requires the synthesis of alternate functional groups. Here, we demonstrate that the addition of Zr(IV) ions into the interiors of reverse micelles having phosphonate functional groups transforms the supramolecular materials from ones that selectively bind positively-charged peptides into materials that selectively bind phosphorylated peptides...
August 11, 2017: Langmuir: the ACS Journal of Surfaces and Colloids
https://www.readbyqxmd.com/read/28802736/synthesis-of-pegylated-polyglutamic-acid-peptide-dendrimer-and-its-application-in-dissolving-thrombus
#4
Shao-Fei Zhang, Chunmei Gao, Shaoyu Lü, Jiujun He, Mingzhu Liu, Can Wu, Yijing Liu, Xinyu Zhang, Zhen Liu
Nattokinase (NK) has been used as a new generation thrombolytic drug, due to its high safety, low cost and low side effects. However, it is sensitive to external environment and may lose the enzyme activity easily. Peptide dendrimer possesses functional groups on its surface, adjustable sizes, biodegradability, biocompatibility, and low toxicity, which could be used as ideal carrier for drug protection and delivery. Demonstrated for the first time in this paper, a PEGylated dendrimer (Gn-PEG-Gn) composed of polyglutamic acid is designed and synthesized as delivery platform of NK for thrombus treatment...
August 4, 2017: Colloids and Surfaces. B, Biointerfaces
https://www.readbyqxmd.com/read/28799768/total-synthesis-and-stereochemical-assignment-of-gymnopeptides-a-and-b
#5
Zhengyin Pan, Chunlei Wu, Wei Wang, Zhehong Cheng, Guiyang Yao, Ke Liu, Hongchang Li, Lijing Fang, Wu Su
Gymnopeptides A and B are unprecedented highly N-methylated cyclic β-hairpin octadecapeptides with striking antiproliferative activities isolated from the mushroom Gymnopus fusipes. Using Fmoc-based solid-phase peptide synthesis, followed by macrolactamization of the resulting linear peptides, the first total synthesis of gymnopeptides A and B was successfully achieved in this study. The coupling methods used for the solid-phase synthesis and the cyclization were optimized, and the configuration of the Ser1/Thr1 residue in gymnopeptide A/B was determined to be l...
August 11, 2017: Organic Letters
https://www.readbyqxmd.com/read/28799023/expression-of-cholesterol-hydroxylase-lyase-system-proteins-in-yeast-s-cerevisiae-cells-as-a-self-processing-polyprotein
#6
Vera S Efimova, Ludmila V Isaeva, Desislava S Makeeva, Mikhail A Rubtsov, Ludmila A Novikova
2A peptide discovered in Picornaviridae is capable of self-cleavage providing an opportunity to carry out synthesis of several proteins using one transcript. Dissociation in the 2A sequence during translation leads to the individual proteins formation. We constructed cDNA including genes of the bovine cholesterol hydroxylase/lyase (CHL) system proteins-cytochrome P450scc (CYP11A1), adrenodoxin (Adx) and adrenodoxin reductase (AdR), that are fused into a single ORF using FMDV 2A nucleotide sequences. The constructed vectors direct the expression of cDNA encoding polyprotein P450scc-2A-Adx-2A-AdR (CHL-2A) in Escherichia coli and Saccharomyces cerevisiae...
August 10, 2017: Molecular Biotechnology
https://www.readbyqxmd.com/read/28797801/dimeric-and-trimeric-homo-and-heteroleptic-hydroxamic-acid-macrocycles-formed-using-mixed-ligand-fe-iii-based-metal-templated-synthesis
#7
Athavan Sresutharsan, William Tieu, Tomas Richardson-Sanchez, Cho Zin Soe, Rachel Codd
Macrocyclic hydroxamic acids coordinate Fe(III) with high affinity as part of siderophore-mediated bacterial iron acquisition. Trimeric hydroxamic acid macrocycles, such as desferrioxamine E (DFOE), are prevalent in nature, with fewer dimeric macrocycles identified, including putrebactin (pbH2), avaroferrin (avH2), bisucaberin (bsH2) and alcaligin (alH2). This work used metal-templated synthesis (MTS) to pre-assemble complexes between one equivalent of Fe(III) and two equivalents of 4-((4-aminobutyl)(hydroxy)amino)-4-oxobutanoic acid (BBH) or 4-((5-aminopentyl)(hydroxy)amino)-4-oxobutanoic acid (PBH)...
August 1, 2017: Journal of Inorganic Biochemistry
https://www.readbyqxmd.com/read/28797773/methyl-propiolate-and-3-butynone-starting-points-for-synthesis-of-amphiphilic-1-2-3-triazole-peptidomimetics-for-antimicrobial-evaluation
#8
Thomas A Bakka, Morten B Strøm, Jeanette H Andersen, Odd R Gautun
A library of 29 small 1,4-substituted 1,2,3-triazoles was prepared for studies of antimicrobial activity. The pharmacophore model investigated with these substrates was based on small peptidomimetics of antimicrobial peptides and antimicrobials isolated from marine organisms from sub-arctic regions. Using methyl 1,2,3-triazole-carboxylates and 1,2,3-triazole methyl ketones prepared through "click" chemistry we were able to synthesize the different cationic amphiphiles through three steps or less. Several structural modifications to the lipopohilic side and hydrophilic sides of the amphiphiles were investigated and compared with regards to antimicrobial activity and cytotoxicity in particular...
July 29, 2017: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/28797234/succinyl-proteome-profiling-of-dendrobium-officinale-an-important-traditional-chinese-orchid-herb-revealed-involvement-of-succinylation-in-the-glycolysis-pathway
#9
Shangguo Feng, Kaili Jiao, Hong Guo, Mengyi Jiang, Juan Hao, Huizhong Wang, Chenjia Shen
BACKGROUND: Lysine succinylation is a ubiquitous and important protein post-translational modification in various eukaryotic and prokaryotic cells. However, its functions in Dendrobium officinale, an important traditional Chinese orchid herb with high polysaccharide contents, are largely unknown. RESULTS: In our study, LC-MS/MS was used to identify the peptides that were enriched by immune-purification with a high-efficiency succinyl-lysine antibody. In total, 314 lysine succinylation sites in 207 proteins were identified...
August 10, 2017: BMC Genomics
https://www.readbyqxmd.com/read/28797123/relationship-between-plasma-xanthine-oxidoreductase-activity-and-left-ventricular-ejection-fraction-and-hypertrophy-among-cardiac-patients
#10
Yuki Fujimura, Yohei Yamauchi, Takayo Murase, Takashi Nakamura, Shu-Ichi Fujita, Tomohiro Fujisaka, Takahide Ito, Koichi Sohmiya, Masaaki Hoshiga, Nobukazu Ishizaka
BACKGROUND AND PURPOSE: Xanthine oxidoreductase (XOR), which catalyzes purine catabolism, has two interconvertible forms, xanthine dehydrogenase and xanthine oxidase, the latter of which produces superoxide during uric acid (UA) synthesis. An association between plasma XOR activity and cardiovascular and renal outcomes has been previously suggested. We investigated the potential association between cardiac parameters and plasma XOR activity among cardiology patients. METHODS AND RESULTS: Plasma XOR activity was measured by [13C2,15N2]xanthine coupled with liquid chromatography/triplequadrupole mass spectrometry...
2017: PloS One
https://www.readbyqxmd.com/read/28796473/multifunctional-%C3%AE-v%C3%AE-6-integrin-specific-peptide-pt-iv-conjugates-for-cancer-cell-targeting
#11
Anne C Conibear, Sonja Hager, Josef Mayr, Matthias H M Klose, Bernhard K Keppler, Christian R Kowol, Petra Heffeter, Christian F W Becker
Increasing the specificity of cancer therapy, and thereby decreasing damage to normal cells, requires targeting to cancer-cell specific features. The αvβ6 integrin is a receptor involved in cell adhesion and is frequently up-regulated in cancer cells compared to normal cells. We have selected a peptide ligand reported to bind specifically to the β6 integrin and have synthesized a suite of multispecific molecules to explore the potential for targeting of cancer cells. A combination of solid-phase peptide synthesis and chemoselective ligations was used to synthesize multifunctional molecules composed of integrin-targeting peptides, cytotoxic platinum(IV) prodrugs, and fluorescent or affinity probes joined with flexible linkers...
August 10, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28796369/facile-synthesis-of-multiblock-copolymers-containing-sequence-controlled-peptides-and-well-defined-vinyl-polymers-via-nitroxide-mediated-polymerization
#12
Shin-Nosuke Nishimura, Nobuyuki Higashi, Tomoyuki Koga
Precisely incorporating a wide range of structural and functional multiblocks along the polymer backbone is a significant challenge in polymer chemistry and offers promising opportunities to design highly ordered materials, including controlled polymer folding. Herein we report a facile and versatile strategy for preparing functional multiblock copolymers composed of sequential peptides and well-defined vinyl polymers with a narrow polydispersity. We develop cyclic oligopeptides containing an alkoxyamine bond in the framework...
August 10, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/28795795/mass-defect-based-dimethyl-pyrimidinyl-ornithine-dipyro-tags-for-multiplex-quantitative-proteomics
#13
Dustin C Frost, Amanda R Buchberger, Lingjun Li
We have developed a novel amine-reactive mass defect-based chemical tag, dimethyl pyrimidinyl ornithine (DiPyrO), that is compact in size, is suitable for various biological samples, and enables highly multiplexed quantification of peptides at the MS1 level without increasing mass spectral complexity. The DiPyrO tag structure incorporates heavy isotopes in a variety of configurations to impart as much as 45.3 mDa or as little as 5.8 mDa per tag between labeled peptides. Notably, peptides containing lysine are labeled with two tags, doubling the imparted mass defect to up to 90...
August 10, 2017: Analytical Chemistry
https://www.readbyqxmd.com/read/28794942/homochirality-of-%C3%AE-peptides-a-significant-biomimetic-property-of-unnatural-systems
#14
István M Mándity, Imane Nekkaa, Gábor Paragi, Ferenc Fülöp
Homochirality, an interesting phenomenon of life, is mainly an unresolved problem and was thought to be a property of living matter. Herein, we show that artificial β-peptides have the tendency toward homochiral diastereoselective chain elongation. Chain-length-dependent stereochemical discrimination was investigated in the synthesis of foldamers with various side chains and secondary structures. It was found that there is a strong tendency toward the synthesis of homochiral oligomers. The size of the side chain drastically influenced the selectivity of the stereodiscriminative chain-elongation reaction...
August 2017: ChemistryOpen
https://www.readbyqxmd.com/read/28794451/vitamin-b12-as-a-carrier-of-peptide-nucleic-acid-pna-into-bacterial-cells
#15
Marcin Równicki, Monika Wojciechowska, Aleksandra J Wierzba, Jakub Czarnecki, Dariusz Bartosik, Dorota Gryko, Joanna Trylska
Short modified oligonucleotides targeted at bacterial DNA or RNA could serve as antibacterial agents provided that they are efficiently taken up by bacterial cells. However, the uptake of such oligonucleotides is hindered by the bacterial cell wall. To overcome this problem, oligomers have been attached to cell-penetrating peptides, but the efficiency of delivery remains poor. Thus, we have investigated the ability of vitamin B12 to transport peptide nucleic acid (PNA) oligomers into cells of Escherichia coli and Salmonella Typhimurium...
August 9, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28793176/neutralization-of-pathogenic-fungi-with-small-molecule-immunotherapeutics
#16
Egor Chirkin, Viswanathan Muthusamy, Paul Mann, Terry Roemer, Philippe G Nantermet, David Spiegel
Systemic fungal infections represent an important public health concern, and new antifungal agents are highly desirable. Herein, we describe the design, synthesis and biological evaluation of a novel class of antifungal compounds called Antibody-Recruiting Molecules targeting Fungi (ARM-Fs). Our approach relies on the use of non-peptidic small molecules, which selectively bind fungal cells and recruit endogenous antibodies to their surfaces, resulting in immune-mediated clearance. Using the opportunistic fungal pathogen Candida albicans as a model, we identified a highly specific bifunctional molecule able to mediate the engulfment and phagocytosis of C...
August 9, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/28792693/serum-hepcidin-levels-in-multiple-myeloma
#17
Manolov Victor, Hadjiev Evgeniy, Tzvetkova Gergana, Petrova Julia, Vasilev Vasil, Marinov Borislav, Bogov Ivo, Gramatikova Zlatina, Tzatchev Kamen
BACKGROUND: Multiple myeloma (MM) is a malignant disease with a 10% frequency among all haematology neoplasms. It is characterized by clone proliferation of plasmatic cells in bone marrow, monoclonal gammopathy, and anemia, hypercalcemia, and kidney failure and bone lesions. IL-6 is an inflammatory cytokine, potential growth factor for myeloma cells, as elevated serum levels are connected with poor disease prognosis. IL-6 modulates many gene transcriptions, encoding synthesis of acute phase proteins, including C-reactive protein (CRP) and hepcidin...
July 1, 2017: Clinical Laboratory
https://www.readbyqxmd.com/read/28792680/transcriptomic-basis-of-genome-by-genome-variation-in-a-legume-rhizobia-mutualism
#18
Liana T Burghardt, Joseph Guhlin, Chan Lan Chun, Junqi Liu, Michael J Sadowsky, Robert M Stupar, Nevin D Young, Peter Tiffin
In the legume-rhizobia mutualism, the benefit each partner derives from the other depends on the genetic identity of both host and rhizobial symbiont. To gain insight into the extent of genome x genome interactions on hosts at the molecular level and to identify potential mechanisms responsible for the variation, we examined host gene expression within nodules (the plant organ where the symbiosis occurs) of four genotypes of Medicago truncatula grown with either Ensifer meliloti or E. medicae symbionts. These host x symbiont combinations show significant variation in nodule and biomass phenotypes...
August 9, 2017: Molecular Ecology
https://www.readbyqxmd.com/read/28790894/anatomical-organization-of-urocortin-3-synthesizing-neurons-and-immunoreactive-terminals-in-the-central-nervous-system-of-non-human-primates-sapajus-spp
#19
Daniella S Battagello, Giovanne B Diniz, Paulo L Candido, Joelcimar M da Silva, Amanda R de Oliveira, Kelly R Torres da Silva, Claudimara F P Lotfi, José A de Oliveira, Luciane V Sita, Cláudio A Casatti, David A Lovejoy, Jackson C Bittencourt
Urocortin 3 (UCN3) is a neuropeptide member of the corticotropin-releasing factor (CRF) peptide family that acts as a selective endogenous ligand for the CRF, subtype 2 (CRF2) receptor. Immunohistochemistry and in situ hybridization data from rodents revealed UCN3-containing neurons in discrete regions of the central nervous system (CNS), such as the medial preoptic nucleus, the rostral perifornical area (PFA), the medial nucleus of the amygdala and the superior paraolivary nucleus. UCN3-immunoreactive (UCN3-ir) terminals are distributed throughout regions that mostly overlap with regions of CRF2 messenger RNA (mRNA) expression...
2017: Frontiers in Neuroanatomy
https://www.readbyqxmd.com/read/28789897/functionalization-of-peptide-nucleolipid-bioconjugates-and-their-structure-anti-cancer-activity-relationship-studies
#20
Niki Rana, Christopher Cultrara, Mariana Phillips, David Sabatino
In the search for more potent peptide-based anti-cancer conjugates the generation of new, functionally diverse nucleolipid derived D-(KLAKLAK)2-AK sequences has enabled a structure and anti-cancer activity relationship study. A reductive amination approach was key for the synthesis of alkylamine, diamine and polyamine derived nucleolipids as well as those incorporating heterocyclic functionality. The carboxy-derived nucleolipids were then coupled to the C-terminus of the D-(KLAKLAK)2-AK killer peptide sequence and produced with and without the FITC fluorophore for investigating biological activity in cancer cells...
July 26, 2017: Bioorganic & Medicinal Chemistry Letters
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