Browse
Submit Data
Databases
API
Help

Dataset Information

10 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Nucleobase morpholino ? amino acids as molecular chimeras for the preparation of photoluminescent materials from ribonucleosides.

ABSTRACT: Bioinspired smart materials represent a tremendously growing research field and the obtainment of new building blocks is at the molecular basis of this technology progress. In this work, colloidal materials have been prepared in few steps starting from ribonucleosides. Nucleobase morpholino ?-amino acids are the chimera key intermediates allowing Phe-Phe dipeptides' functionalization with adenine and thymine. The obtained compounds self-aggregate showing enhanced photoluminescent features, such as deep blue fluorescence and phosphorescence emissions.

SUBMITTER: Bucci R

PROVIDER: S-EPMC7652887 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Nucleobase morpholino β amino acids as molecular chimeras for the preparation of photoluminescent materials from ribonucleosides.

Bucci Raffaella R Bossi Alberto A Erba Emanuela E Vaghi Francesco F Saha Abhijit A Yuran Sivan S Maggioni Daniela D Gelmi Maria Luisa ML Reches Meital M Pellegrino Sara S

Scientific reports 20201109 1

Bioinspired smart materials represent a tremendously growing research field and the obtainment of new building blocks is at the molecular basis of this technology progress. In this work, colloidal materials have been prepared in few steps starting from ribonucleosides. Nucleobase morpholino β-amino acids are the chimera key intermediates allowing Phe-Phe dipeptides' functionalization with adenine and thymine. The obtained compounds self-aggregate showing enhanced photoluminescent features, such ...[more]

PMID: 33168883

Similar Datasets

A naphthalene-containing amino acid enables hydrogelation of a conjugate of nucleobase-saccharide-amino acids.

Project description:Here we report the first example of a hydrogelator made of a conjugate of nucleobase-saccharide-amino acids by incorporating L-3-(2-naphthyl)-alanine to the conjugate, which illustrates a facile and effective method for generating bioactive and functional hydrogelators from the basic biological building blocks.

| S-EPMC3974899 | biostudies-literature

Insensitive ionic bio-energetic materials derived from amino acids.

Project description:Energetic salts/ionic liquids have received increasing attention as fascinating energetic materials, and the use of renewable compounds is a promising approach to developing energetic materials. Until recently, biomolecules have been used as raw materials to develop neutral energetic compounds, whereas research focused on ionic energetic materials obtained from natural bio-renewable frameworks is scarce. This work systematically investigates ionic bio-energetic materials (IBEMs) derived from sustainable natural amino acids. In addition to combustibility, high density, good thermal stability, and one-step preparation, these IBEMs demonstrated apparent hypotoxicity and insensitivity. Moreover, a theoretical examination was performed to explore their appropriate properties. The intriguing results of this study indicates that IBEMs are potential bio-based energetic materials.

| S-EPMC5630594 | biostudies-literature

Enhanced Binding Affinity for an i-Motif DNA Substrate Exhibited by a Protein Containing Nucleobase Amino Acids.

Project description:Several variants of a nucleic acid binding motif (RRM1) of putative transcription factor hnRNP LL containing nucleobase amino acids at specific positions have been prepared and used to study binding affinity for the BCL2 i-motif DNA. Molecular modeling suggested a number of amino acids in RRM1 likely to be involved in interaction with the i-motif DNA, and His24 and Arg26 were chosen for modification based on their potential ability to interact with G14 of the i-motif DNA. Four nucleobase amino acids were introduced into RRM1 at one or both of positions 24 and 26. The introduction of cytosine nucleobase 2 into position 24 of RRM1 increased the affinity of the modified protein for the i-motif DNA, consistent with the possible Watson-Crick interaction of 2 and G14. In comparison, the introduction of uracil nucleobase 3 had a minimal effect on DNA affinity. Two structurally simplified nucleobase analogues (1 and 4) lacking both the N-1 and the 2-oxo substituents were also introduced in lieu of His24. Again, the RRM1 analogue containing 1 exhibited enhanced affinity for the i-motif DNA, while the protein analogue containing 4 bound less tightly to the DNA substrate. Finally, the modified protein containing 1 in lieu of Arg26 also bound to the i-motif DNA more strongly than the wild-type protein, but a protein containing 1 both at positions 24 and 26 bound to the DNA less strongly than wild type. The results support the idea of using nucleobase amino acids as protein constituents for controlling and enhancing DNA-protein interaction. Finally, modification of the i-motif DNA at G14 diminished RRM1-DNA interaction, as well as the ability of nucleobase amino acid 1 to stabilize RRM1-DNA interaction.

| S-EPMC5901667 | biostudies-literature

Preparation of Multicolor Photoluminescent Carbon Dots by Tuning Surface States.

Project description:The achievements of multicolor photoluminescent (PL)-emissive carbon dots (CDs), particularly red to near infrared (NIR), are critical for their applications in optoelectronic devices and bioimaging, but it still faces great challenges to date. In this study, PL emission red-shifts were observed when tartaric acid (TA) was added into m-phenylenediamine (mPD) or o-phenylenediamine (oPD) solutions as carbon sources to prepare CDs, i.e., from blue to green for mPD and from yellow-green to red for oPD. Morphology and structure analyses revealed that the increased surface oxidation and carboxylation were responsible for the red-shifts of emission, indicating that TA played a key role in tuning the surface state of CDs. These factors could be employed as effective strategies to adjust PL emissions of CDs. Consequently, multicolor PL CDs (i.e., blue-, green-, yellow-green- and red-emissive CDs) can be facilely prepared using mPD and oPD in the absence and presence of TA. Particularly, the obtained red-emissive CDs showed a high PL quantum yield up to 22.0% and an emission covering red to NIR regions, demonstrating great potentials in optoelectronic devices and bioimaging. Moreover, multicolor phosphors were further prepared by mixing corresponding CDs with polyvinylpyrrolidone (PVP), among which the blue, green, and red ones could serve as three primary color phosphors for fabricating multicolor and white light-emitting diodes (LEDs). The white LED was measured to show a Commission Internationale de L'Eclairage (CIE) 1931 chromaticity coordinate of (0.34, 0.32), a high color rendering index (CRI) of 89, and a correlated color temperature (CCT) of 5850 K, representing one of the best performances of white LEDs based on CDs.

| S-EPMC6523770 | biostudies-literature

Transaminases for the synthesis of enantiopure beta-amino acids.

Project description:Optically pure ?-amino acids constitute interesting building blocks for peptidomimetics and a great variety of pharmaceutically important compounds. Their efficient synthesis still poses a major challenge. Transaminases (also known as aminotransferases) possess a great potential for the synthesis of optically pure ?-amino acids. These pyridoxal 5'-dependent enzymes catalyze the transfer of an amino group from a donor substrate to an acceptor, thus enabling the synthesis of a wide variety of chiral amines and amino acids. Transaminases can be applied either for the kinetic resolution of racemic compounds or the asymmetric synthesis starting from a prochiral substrate. This review gives an overview over microbial transaminases with activity towards ?-amino acids and their substrate spectra. It also outlines current strategies for the screening of new biocatalysts. Particular emphasis is placed on activity assays which are applicable to high-throughput screening.

| S-EPMC3281772 | biostudies-literature

Polyaniline Doping by α,α-Difluoro-β-amino Acids.

Project description:Currently, polyaniline (PANI) is considered as a promising polymer that can be used in biosensors, drug delivery systems, bioelectronics, etc. Its biocompatibility can be strongly improved by using dopants with biofunctionality. This study reveals the protonation/doping of PANI by fluorinated analogs of natural amino acids, namely, α,α-difluoro-β-amino acids (DFAAs) with alkyl and aromatic tails in N-methylpyrrolidone solutions. We find that these acids can dope PANI due to both the weakened basicity of their amino groups because of two fluorine atoms in α,α-positions and specific intermolecular interactions (π-π stacking, alkyl-π, F-π) of their tails with units of PANI chains. These interactions did not give the doped PANI salts with high conductivity but led to formation of stable PANI-DFAA complexes, which were confirmed both by clear changes in the UV-Vis and Fourier transform infrared spectra of the protonated/doped PANI and by their conductivity of ∼10-6 S/cm. Our results suggest an applicability of such PANI complexes as carriers of DFAA for their biomedical applications.

| S-EPMC6649075 | biostudies-literature

Isonitrile-Based Multicomponent Synthesis of β-Amino Boronic Acids as β-Lactamase Inhibitors.

Project description:The application of various isonitrile-based multicomponent reactions to protected (2-oxoethyl)boronic acid (as the carbonyl component) is described. The Ugi reaction, both in the four components and in the four centers-three components versions, and the van Leusen reaction, proved effective at providing small libraries of MIDA-protected β-aminoboronic acids. The corresponding free β-aminoboronic acids, quantitatively recovered through basic mild deprotection, were found to be quite stable and were fully characterized, including by 11B-NMR spectroscopy. Single-crystal X-ray diffraction analysis, applied both to a MIDA-protected and a free β-aminoboronic acid derivative, provided evidence for different conformations in the solid-state. Finally, the antimicrobial activities of selected compounds were evaluated by measuring their minimal inhibitory concentration (MIC) values, and the binding mode of the most promising derivative on OXA-23 class D β-lactamase was predicted by a molecular modeling study.

| S-EPMC7277116 | biostudies-literature

Synthesis of novel conjugates of a saccharide, amino acids, nucleobase and the evaluation of their cell compatibility.

Project description:This article reports the synthesis of a novel type of conjugate of three fundamental biological build blocks (i.e., saccharide, amino acids, and nucleobase) and their cell compatibility. The facile synthesis starts with the synthesis of nucleobase and saccharide derivatives, then uses solid-phase peptide synthesis (SPPS) to build the peptide segment (Phe-Arg-Gly-Asp or naphthAla-Phe-Arg-Gly-Asp with fully protected groups), and later, an amidation reaction in liquid phase connects these three parts together. The overall yield of these multiple step synthesis is about 34%. Besides exhibiting excellent solubility, these conjugates of saccharide-amino acids-nucleobase (SAN), like the previously reported conjugates of nucleobase-amino acids-saccharide (NAS) and nucleobase-saccharide-amino acids (NSA), are mammalian cell compatible.

| S-EPMC4222440 | biostudies-other

Catalytic Asymmetric Synthesis of Unprotected β<sup>2</sup>-Amino Acids.

Project description:We report here a scalable, catalytic one-pot approach to enantiopure and unmodified β2-amino acids. A newly developed confined imidodiphosphorimidate (IDPi) catalyzes a broadly applicable reaction of diverse bis-silyl ketene acetals with a silylated aminomethyl ether, followed by hydrolytic workup, to give free β2-amino acids in high yields, purity, and enantioselectivity. Importantly, both aromatic and aliphatic β2-amino acids can be obtained using this method. Mechanistic studies are consistent with the aminomethylation to proceed via silylium-based asymmetric counteranion-directed catalysis (Si-ACDC) and a transition state to explain the enantioselectivity is suggested on the basis of density functional theory calculation.

| S-EPMC7953379 | biostudies-literature

Template-Assisted Preparation of Micrometric Suspended Membrane Lattices of Photoluminescent and Non-Photoluminescent Polymers by Capillarity-Driven Solvent Evaporation: Application to Microtagging.

Project description:In this work, the bottom-up template-assisted preparation of high-density lattices (up to 11?·?106?membranes/cm2) of suspended polymer membranes with micrometric size (in the order of few ?m2) and sub-micrometric thickness (in the order of hundreds of nm) is demonstrated for both photoluminescent and non-photoluminescent polymers by capillarity-driven solvent evaporation. Solvent evaporation of low concentration polymer solutions drop-cast on an array of open-ended micropipes is shown to lead to polymer membrane formation at the inlet of the micropipes thanks to capillarity. The method is proven to be robust with high-yield (>98%) over large areas (1?cm2) and of general validity for both conjugated and non-conjugated polymers, e.g. poly(9,9-di-n-octylfluorene-alt-benzothiadiazole (F8BT), poly[2-methoxy-5-(3',7'-dimethyloctyloxy)-1,4-phenylenevinylene] (MDMO-PPV), polystyrene (PS), thus breaking a new ground on the controlled preparation of polymer micro and nanostructures. Angle dependence and thermal stability of photoluminescence emission arising from F8BT membrane lattices was thorough investigated, highlighting a non-Lambertian photoluminescence emission of membrane lattices with respect to F8BT films. The method is eventually successfully applied to the preparation of both photoluminescent and non-photoluminescent micro Quick Response (?QR) codes using different polymers, i.e. F8BT, MDMO-PPV, PS, thus providing micrometric-sized taggants suitable for anti-counterfeiting applications.

| S-EPMC5566329 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data