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Peptide synthesis

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https://www.readbyqxmd.com/read/29786419/multifunctional-high-molecular-weight-post-translationally-modified-proteins-through-oxidative-cysteine-coupling-and-tyrosine-modification
#1
Brian M Seifried, James Cao, Bradley D Olsen
Glycoproteins and their mimics are challenging to produce via chemical or biological methods because of their long protein backbones and large number of polysaccharide side chains that form a densely grafted protein-polysaccharide brush architecture. Herein, we demonstrate a new approach to protein bioconjugate synthesis that can approach the molar mass and functionalization densities of natural glycoproteins such as mucins and aggrecans. In this method, a tyrosine-enriched protein sequence is engineered and synthesized in E...
May 22, 2018: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/29784775/recombinant-escherichia-coli-as-a-biofactory-for-various-single-and-multi-element-nanomaterials
#2
Yoojin Choi, Tae Jung Park, Doh C Lee, Sang Yup Lee
Nanomaterials (NMs) are mostly synthesized by chemical and physical methods, but biological synthesis is also receiving great attention. However, the mechanisms for biological producibility of NMs, crystalline versus amorphous, are not yet understood. Here we report biosynthesis of 60 different NMs by employing a recombinant Escherichia coli strain coexpressing metallothionein, a metal-binding protein, and phytochelatin synthase that synthesizes a metal-binding peptide phytochelatin. Both an in vivo method employing live cells and an in vitro method employing the cell extract are used to synthesize NMs...
May 21, 2018: Proceedings of the National Academy of Sciences of the United States of America
https://www.readbyqxmd.com/read/29783946/novel-flax-orbitide-derived-from-genetic-deletion
#3
Peta-Gaye Gillian Burnett, Lester Warren Young, Clara Marisa Olivia, Pramodkumar Dinkar Jadhav, Denis Paskal Okinyo-Owiti, Martin John Tarsisius Reaney
BACKGROUND: Flaxseed orbitides are homodetic plant cyclic peptides arising from ribosomal synthesis and post-translation modification (N to C cyclization), and lacking cysteine double bonds (Nat Prod Rep 30:108-160, 2013). Screening for orbitide composition was conducted on the flax core collection (FCC) grown at both Saskatoon, Saskatchewan and Morden, Manitoba over three growing seasons (2009-2011). Two flax (Linum usitatissimum L.) accessions 'Hollandia' (CN 98056) and 'Z 11637' (CN 98150) produce neither [1-9-NαC]-linusorb B2 (3) nor [1-9-NαC]-linusorb B3 (1)...
May 21, 2018: BMC Plant Biology
https://www.readbyqxmd.com/read/29782177/synthesis-of-%C3%AE-%C3%AE-difluorinated-phosphonate-pser-pthr-mimetics-via-rhodium-catalyzed-asymmetric-hydrogenation-of-%C3%AE-difluorophosphonomethyl-%C3%AE-acylamino-acrylates
#4
Hong-Xue Chen, Jie Kang, Rong Chang, Yun-Lai Zhang, Hua-Zhen Duan, Yan-Mei Li, Yong-Xiang Chen
A novel and facile synthetic strategy for α,α-difluorinated phosphonate mimetics of phosphoserine/phosphothreonine utilizing rhodium-catalyzed asymmetric hydrogenation was developed. The dehydrogenated substrate β-difluorophosphonomethyl α-(acylamino)acrylates were first prepared from protected serine/threonine followed by asymmetric hydrogenation using the rhodium-DuPhos catalytic system to generate the chiral center(s). These important phosphonate building blocks were successfully incorporated into phosphatase-resistant peptides, which displayed similar inhibition to the 14-3-3 ζ protein as the parent pSer/pThr peptides...
May 21, 2018: Organic Letters
https://www.readbyqxmd.com/read/29779845/effects-of-estradiol-on-lactoprivic-signaling-of-the-hindbrain-upon-the-contraregulatory-hormonal-response-and-metabolic-neuropeptide-synthesis-in-hypoglycemic-female-rats
#5
Santosh K Mandal, Prem K Shrestha, Fahaad S H Alenazi, Manita Shakya, Hussain N Alhamami, Karen P Briski
BACKGROUND: Caudal dorsomedial hindbrain detection of hypoglycemia-associated lactoprivation regulates glucose counter-regulation in male rats. In females, estradiol (E) determines hypothalamic neuroanatomical and molecular foci of hindbrain energy sensor activation. This study investigated the hypothesis that E signal strength governs metabolic neuropeptide and counter-regulatory hormone responses to hindbrain lactoprivic stimuli in hypoglycemic female rats. METHODS: Ovariectomized animals were implanted with E-filled silastic capsules [30 (E-30) or 300 μg (E-300)/mL] to replicate plasma concentrations at estrous cycle nadir versus peak levels...
May 17, 2018: Neuropeptides
https://www.readbyqxmd.com/read/29779659/preparation-assay-and-application-of-chlorinase-sall-for-the-chemoenzymatic-synthesis-of-s-adenosyl-l-methionine-and-analogs
#6
Tony D Davis, Sylvia Kunakom, Michael D Burkart, Alessandra S Eustaquio
S-adenosyl-l-methionine (SAM) is universal in biology, serving as the second most common cofactor in a variety of enzymatic reactions. One of the main roles of SAM is the methylation of nucleic acids, proteins, and metabolites. Methylation often imparts regulatory control to DNA and proteins, and leads to an increase in the activity of specialized metabolites such as those developed as pharmaceuticals. There has been increased interest in using SAM analogs in methyltransferase-catalyzed modification of biomolecules...
2018: Methods in Enzymology
https://www.readbyqxmd.com/read/29779651/the-biochemistry-and-structural-biology-of-cyanobactin-pathways-enabling-combinatorial-biosynthesis
#7
Wenjia Gu, Shi-Hui Dong, Snigdha Sarkar, Satish K Nair, Eric W Schmidt
Cyanobactin biosynthetic enzymes have exceptional versatility in the synthesis of natural and unnatural products. Cyanobactins are ribosomally synthesized and posttranslationally modified peptides synthesized by multistep pathways involving a broad suite of enzymes, including heterocyclases/cyclodehydratases, macrocyclases, proteases, prenyltransferases, methyltransferases, and others. Here, we describe the enzymology and structural biology of cyanobactin biosynthetic enzymes, aiming at the twin goals of understanding biochemical mechanisms and biosynthetic plasticity...
2018: Methods in Enzymology
https://www.readbyqxmd.com/read/29777693/cleavage-of-molybdopterin-synthase-moad-moae-linear-fusion-by-jamm-mpn-domain-containing-metalloprotease-dr0402-from-deinococcus-radiodurans
#8
Yoon-Mo Yang, Young-Bin Won, Chang-Jun Ji, Jung-Hoon Kim, Su-Hyun Ryu, Youn-Ha Ok, Jin-Won Lee
Molybdenum cofactor (Moco), molybdopterin (MPT) complexed with molybdenum, is an essential cofactor required for the catalytic center of diverse enzymes in all domains of life. Since Moco cannot be taken up as a nutrient unlike many other cofactors, Moco requires de novo biosynthesis. During the synthesis of MPT, the sulfur atom on the C-terminus of MoaD is transferred to cyclic pyranopterin monophosphate (cPMP) which is bound in the substrate pocket of MoaE. MoaD is a ubiquitin-like (Ubl) protein and has a C-terminal di-Gly motif which is a common feature of Ubl proteins...
May 16, 2018: Biochemical and Biophysical Research Communications
https://www.readbyqxmd.com/read/29776930/modifying-the-lantibiotic-mutacin-1140-for-increased-yield-activity-and-stability
#9
Mengxin Geng, Leif Smith
Mutacin 1140 belongs to the epidermin family of type AI lantibiotics. This family has a broad spectrum of activity against Gram-positive bacteria. The binding of mutacin 1140 to lipid II leads to the inhibition of cell wall synthesis. Pharmacokinetic experiments on type AI lantibiotics are generally discouraging for clinical applications due to their short half-life. The unprotected dehydrated and protease susceptible residues outside of the lanthionine rings may play a role in their short half-life in physiological settings...
May 18, 2018: Applied and Environmental Microbiology
https://www.readbyqxmd.com/read/29775706/purification-and-characterization-of-an-organic-solvent-tolerant-and-detergent-stable-lipase-from-haloferax-mediterranei-cncmm-50101
#10
Siham Akmoussi-Toumi, Souad Khemili-Talbi, Imen Ferioune, Salima Kebbouche-Gana
The present study investigates the purification and biochemical characterization of an extracellular lipase (HML) from Haloarchaea Haloferax mediterranei strain ATS1, isolated from the Sebkha (Medea, Algeria). The pure protein was obtained with ammonium sulfate precipitation (40-70%)-dialysis and UNO Q-6 FPLC, and characterized biochemically. Matrix assisted laser desorption ionization-time of flight mass spectrometry (MALDI-TOF/MS) analysis revealed that the purified enzyme was a monomer, with a molecular mass of 45,011...
May 15, 2018: International Journal of Biological Macromolecules
https://www.readbyqxmd.com/read/29774920/the-design-and-fabrication-of-supramolecular-semiconductor-nanowires-formed-by-benzothienobenzothiophene-btbt-conjugated-peptides
#11
Mohammad Aref Khalily, Hakan Usta, Mehmet Ozdemir, Gokhan Bakan, F Begum Dikecoglu, Charlotte Edwards-Gayle, Jessica A Hutchinson, Ian W Hamley, Aykutlu Dana, Mustafa O Guler
π-Conjugated small molecules based on a [1]benzothieno[3,2-b]benzothiophene (BTBT) unit are of great research interest in the development of solution-processable semiconducting materials owing to their excellent charge-transport characteristics. However, the BTBT π-core has yet to be demonstrated in the form of electro-active one-dimensional (1D) nanowires that are self-assembled in aqueous media for potential use in bioelectronics and tissue engineering. Here we report the design, synthesis, and self-assembly of benzothienobenzothiophene (BTBT)-peptide conjugates, the BTBT-peptide (BTBT-C3-COHN-Ahx-VVAGKK-Am) and the C8-BTBT-peptide (C8-BTBT-C3-COHN-Ahx-VVAGKK-Am), as β-sheet forming amphiphilic molecules, which self-assemble into highly uniform nanofibers in water with diameters of 11-13(±1) nm and micron-size lengths...
May 18, 2018: Nanoscale
https://www.readbyqxmd.com/read/29774910/design-of-rgd-atwlppr-peptide-conjugates-for-the-dual-targeting-of-%C3%AE-v-%C3%AE-3-integrin-and-neuropilin-1
#12
Fabien Thoreau, Laetitia Vanwonterghem, Maxime Henry, Jean-Luc Coll, Didier Boturyn
Targeting the tumour microenvironment is a promising strategy to detect and/or treat cancer. The design of selective compounds that co-target several receptors frequently overexpressed in solid tumours may allow a reliable and selective detection of tumours. Here we report the modular synthesis of compounds encompassing ligands of αVβ3 integrin and neuropilin-1 that are overexpressed in the tumour microenvironment. These compounds were then evaluated through cellular experiments and imaging of tumours in mice...
May 18, 2018: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/29773062/backbone-cyclized-peptides-a-critical-review
#13
Samuel J S Rubin, Nir Qvit
Backbone-cyclized peptides and peptidomimetics integrate the biological activity and pharmacological features necessary for successful research tools and therapeutics. In general, these structures demonstrate improved maintenance of bioactive conformation, stability and cell permeability compared to their linear counterparts, while maintaining support for a variety of side chain chemistries. We explain how backbone cyclization and cycloscan techniques allow scientists to cyclize linear peptides with retained or enhanced biological activity and improved drug-like features...
May 17, 2018: Current Topics in Medicinal Chemistry
https://www.readbyqxmd.com/read/29772211/synthesis-folding-structure-and-activity-of-a-predicted-peptide-from-the-sea-anemone-oulactis-sp-with-an-shkt-fold
#14
Bankala Krishnarjuna, Jessica Villegas-Moreno, Michela L Mitchell, Agota Csoti, Steve Peigneur, Carlos Amero, Michael W Pennington, Jan Tytgat, Gyorgy Panyi, Raymond S Norton
Sea anemone venom is rich in bioactive compounds, including peptides containing multiple disulfide bridges. In a transcriptomic study on Oulactis sp., we identified the putative 36-residue peptide, OspTx2b, which is an isoform of the KV channel blocker OspTx2a (Sunanda P et al. (2018) Identification, chemical synthesis, structure and function of a new KV 1 channel blocking peptide from Oulactis sp. Peptide Science, in press). As OspTx2b contains a ShK/BgK-like cysteine framework, with high amino acid sequence similarity to BgK, we were interested to investigate its structure and function...
May 14, 2018: Toxicon: Official Journal of the International Society on Toxinology
https://www.readbyqxmd.com/read/29771457/transition-metal-ions-mediated-tyrosine-based-short-peptide-amphiphile-nanostructures-inhibit-bacterial-growth
#15
Khashti Ballabh Joshi, Ramesh Singh, Narendra Kumar Mishra, Vikas Kumar, Vandana Vinayak
We report the design and synthesis of biocompatible small peptide based molecule for the controlled and targeted delivery of the encapsulated bioactive metal ions via transforming their internal nanostructures. Tyrosine based short peptide amphiphile (sPA) was synthesized which self-assembled into β-sheet like secondary structures. The self assembly of the designed sPA was modulated by using different bioactive transition metal ions which is confirmed by spectroscopic and microscopic techniques. These bioactive metal ions conjugated sPA hybrid structures are further used to develop antibacterial materials...
May 17, 2018: Chembiochem: a European Journal of Chemical Biology
https://www.readbyqxmd.com/read/29771428/ampk-regulates-energy-metabolism-through-the-sirt1-signaling-pathway-to-improve-myocardial-hypertrophy
#16
H-W Dong, L-F Zhang, S-L Bao
OBJECTIVE: We investigated the correlations of adenosine monophosphate-activated protein kinase (AMPK), Silence information regulator 1 (SIRT1) and energy metabolism with myocardial hypertrophy. MATERIALS AND METHODS: Myocardial hypertrophy experimental model was established via transverse aortic constriction (TAC)-induced myocardial hypertrophy and phenylephrine (PE)-induced hypertrophic myocardial cell culture. After activation of AMPK, the messenger ribonucleic acid (mRNA) expressions in myocardial tissue- and myocardial cell hypertrophy-related genes, atrial natriuretic peptide (ANP) and β-myosin heavy chain (β-MHC), were detected...
May 2018: European Review for Medical and Pharmacological Sciences
https://www.readbyqxmd.com/read/29768874/nanocarriers-immobilized-proteases-and-their-industrial-applications-an-overview
#17
Qayyum Husain
The enzymes proteases have attracted a lot of attention due to their high demand in various industrial and other sectors since past several decades. Nanosupport bound proteases showed high efficiency of binding and yield of immobilization. Enzymes attached to such support were found significantly more resistant to the denaturation mediated by change in pH and temperature, medium particularly in the presence of water miscible and immiscible organic solvents, detergents, and several kinds of other denaturants...
January 1, 2018: Journal of Nanoscience and Nanotechnology
https://www.readbyqxmd.com/read/29765474/on-the-design-principles-of-peptide-drug-conjugates-for-targeted-drug-delivery-to-the-malignant-tumor-site
#18
REVIEW
Eirinaios I Vrettos, Gábor Mező, Andreas G Tzakos
Cancer is the second leading cause of death affecting nearly one in two people, and the appearance of new cases is projected to rise by >70% by 2030. To effectively combat the menace of cancer, a variety of strategies have been exploited. Among them, the development of peptide-drug conjugates (PDCs) is considered as an inextricable part of this armamentarium and is continuously explored as a viable approach to target malignant tumors. The general architecture of PDCs consists of three building blocks: the tumor-homing peptide, the cytotoxic agent and the biodegradable connecting linker...
2018: Beilstein Journal of Organic Chemistry
https://www.readbyqxmd.com/read/29763546/direct-structural-annotation-of-membrane-protein-aggregation-loci-using-peptide-based-reverse-mapping
#19
Muralikrishna Lella, Radhakrishnan Mahalakshmi
Membrane protein aggregation is associated with neurodegenerative diseases. Despite remarkable advances to map protein aggregation, molecular elements that drive the structural transition from functional to amyloidogenic β-sheet polymers remain elusive. Here, we report a simple and reliable reverse-mapping method to identify the molecular elements. We validate our approach by obtaining molecular details of aggregation loci of human β-barrel nanopore ion channels that are vital for cell survival. By coupling bottom-up synthesis with time-resolved aggregation kinetics and high-resolution imaging, we identify molecular elements that switch folded channels to polymeric β-rich aggregates...
May 15, 2018: Journal of Physical Chemistry Letters
https://www.readbyqxmd.com/read/29762718/cell-penetrating-thiazole-peptides-inhibit-c-myc-expression-via-site-specific-targeting-of-c-myc-g-quadruplex
#20
Debasish Dutta, Manish Debnath, Diana Müller, Rakesh Paul, Tania Das, Irene Bessi, Harald Schwalbe, Jyotirmayee Dash
The structural differences among different G-quadruplexes provide an opportunity for site-specific targeting of a particular G-quadruplex structure. However, majority of G-quadruplex ligands described thus far show little selectivity among different G-quadruplexes. In this work, we delineate the design and synthesis of a crescent-shaped thiazole peptide that preferentially stabilizes c-MYC quadruplex over other promoter G-quadruplexes and inhibits c-MYC oncogene expression. Biophysical analysis such as Förster resonance energy transfer (FRET) melting and fluorescence spectroscopy show that the thiazole peptide TH3 can selectively interact with the c-MYC G-quadruplex over other investigated G-quadruplexes and duplex DNA...
May 14, 2018: Nucleic Acids Research
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