Browse
Submit Data
Databases
API
Help

Dataset Information

7 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis of Disaccharide Nucleosides Utilizing the Temporary Protection of the 2',3'-cis-Diol of Ribonucleosides by a Boronic Ester.

ABSTRACT: Disaccharide nucleosides are an important class of natural compounds that have a variety of biological activities. In this study, we report on the synthesis of disaccharide nucleosides utilizing the temporary protection of the 2',3'-cis-diol of ribonucleosides, such as adenosine, guanosine, uridine, 5-metyluridine, 5-fluorouridine and cytidine, by a boronic ester. The temporary protection of the above ribonucleosides permits the regioselective O-glycosylation of the 5'-hydroxyl group with thioglycosides using a p-toluenesulfenyl chloride (p-TolSCl)/silver triflate (AgOTf) promoter system to afford the corresponding disaccharide nucleosides in fairly good chemical yields. The formation of a boronic ester prepared from uridine and 4-(trifluoromethyl)phenylboronic acid was examined by ¹H, 11B and 19F NMR spectroscopy.

SUBMITTER: Someya H

PROVIDER: S-EPMC6151833 | biostudies-other | 2017 Oct

REPOSITORIES: biostudies-other

ACCESS DATA

Json Xml

Publications

Synthesis of Disaccharide Nucleosides Utilizing the Temporary Protection of the 2',3'-cis-Diol of Ribonucleosides by a Boronic Ester.

Someya Hidehisa H Itoh Taiki T Aoki Shin S

Molecules (Basel, Switzerland) 20171001 10

Disaccharide nucleosides are an important class of natural compounds that have a variety of biological activities. In this study, we report on the synthesis of disaccharide nucleosides utilizing the temporary protection of the 2',3'-cis-diol of ribonucleosides, such as adenosine, guanosine, uridine, 5-metyluridine, 5-fluorouridine and cytidine, by a boronic ester. The temporary protection of the above ribonucleosides permits the regioselective O-glycosylation of the 5'-hydroxyl gro ...[more]

PMID: 28974027

Similar Datasets

Practical silyl protection of ribonucleosides.

Project description:Herein we report the site-selective silylation of the ribonucelosides. The method enables a simple and efficient procedure for accessing suitably protected monomers for automated RNA synthesis. Switching to the opposite enantiomer of the catalyst allows for the selective silylation of the 3'-hydroxyl, which could be used in the synthesis of unnatural RNA or for the analoging of ribonucelosides. Lastly, the procedure was extended to ribavirin a potent antiviral therapeutic.

| S-EPMC3857215 | biostudies-literature

A Simple, Rapid, Fluorometric Assay for Dopamine by In Situ Reaction of Boronic Acids and cis-Diol.

Project description:An efficient, sensitive, and low-cost method has been developed for turn-on fluorescence sensing of dopamine (DA). The method relies on the rapid reaction of DA and 3-Hydroxyphenylboronic acid (3-HPBA) via specific recognition between boronic acids and cis-diol of DA in alkaline solution. The reaction product shows an excitation wavelength of 417 nm and the maximum emission peak at 470 nm. The proposed method allows the determination of DA in the range of 50 nM-25 μM, and the whole detection can be completed within 5 minutes. Furthermore, the presented approach has good selectivity and has been successfully applied to DA sensing in human serum samples, showing great potential in clinical diagnosis.

| S-EPMC6458919 | biostudies-literature

Structure-Reactivity Relationships in Boronic Acid-Diol Complexation.

Project description:Boronic acids have found widespread use in the field of biomaterials, primarily through their ability to bind with biologically relevant 1,2- and 1,3-diols, including saccharides and peptidoglycans, or with polyols to prepare hydrogels with dynamic covalent or responsive behavior. Despite a wide range of boronic acid architectures that have been previously considered, there is a need for greater understanding of the structure-reactivity relationships that govern binding affinity to diols. In this study, various boronic acids and other organoboron compounds were investigated to determine their pK a and their binding constants with the biologically relevant diols including sorbitol, fructose, and glucose. Boronic acid pK a values were determined through spectroscopic titration, whereas binding constants were determined by fluorescence spectroscopy during competitive binding studies. Key structure-reactivity relationships clearly indicated that both boronic acid structure and solution pH must be carefully considered. By considering a variety of boronic acids with systematically varied electronics and sterics, these results provide guidance during selection of organoboron compounds in sensing, delivery, and materials chemistry.

| S-EPMC6644144 | biostudies-literature

Efficiently self-healing boronic ester crystals.

Project description:The perception of organic crystals being rigid static entities is quickly eroding, and molecular crystals are now matching a number of properties previously thought to be unique to soft materials. Here, we present crystals of a boronate ester that encompass many of the elastic and plastic mechanical properties of polymers such as bending, twisting, coiling and highly efficient self-healing of up to 67%, while they maintain their long-range structural order. The approach utilizes the concept of dynamic covalent chemistry and proves it can be applied towards ordered materials. This work expands our current understanding of the properties of crystalline molecular materials, and it could have implications towards the development of mechanically robust organic crystals that are capable of self-repair for durable all-organic electronics and soft robotics.

| S-EPMC8157749 | biostudies-literature

cis-Cyclo-heptane-1,2-diol.

Project description:The title compound, C(7)H(14)O(2), is a vicinal diol derived from cyclo-heptane with cis-orientated hydr-oxy groups. The mol-ecules shows no non-crystallographic symmetry. The O-C-C-O torsion angles of both mol-ecules present in the asymmetric unit [-66.4 (2) and -66.9 (2)°] are similar to those in trans-configured cyclo-hexane derivatives (including pyran-oses) as well as rac-trans-cyclo-heptane-1,2-diol, but smaller than those in trans-configured cyclo-pentane derivatives (including furan-oses). In the crystal structure, O-H⋯O hydrogen bonds furnish the formation of sheets parallel to [110].

| S-EPMC2971971 | biostudies-literature

Profiling of cis-diol-containing nucleosides and ribosylated metabolites by boronate-affinity organic-silica hybrid monolithic capillary liquid chromatography/mass spectrometry.

Project description:RNA contains a large number of modified nucleosides. In the metabolic re-exchange of RNA, modified nucleosides cannot be recycled and are thus excreted from cells into biological fluids. Determination of endogenous modified nucleosides in biological fluids may serve as non-invasive cancers diagnostic methods. Here we prepared boronate-affinity organic-silica hybrid capillary monolithic column (BOHCMC) that exhibited excellent selectivity toward the cis-diol-containing compounds. We then used the prepared BOHCMC as the on-line solid-phase microextraction (SPME) column and developed an on-line SPME-LC-MS/MS method to comprehensively profile cis-diol-containing nucleosides and ribosylated metabolites in human urine. Forty-five cis-diol-containing nucleosides and ribosylated metabolites were successfully identified in human urine. And five ribose conjugates, for the first time, were identified existence in human urine in the current study. Furthermore, the relative quantification suggested 4 cis-diol-containing compounds (5'-deoxy-5'-methylthioadensine, N(4)-acetylcytidine, 1-ribosyl-N-propionylhistamine and N(2),N(2),7-trimethylguanosine) increased more than 1.5 folds in all the 3 types of examined cancers (lung cancer, colorectal cancer, and nasopharyngeal cancer) compared to healthy controls. The on-line SPME-LC-MS/MS method demonstrates a promising method for the comprehensive profiling of cis-diol-containing ribose conjugates in human urines, which provides an efficient strategy for the identification and discovery of biomarkers and may be used for the screening of cancers.

| S-EPMC4293604 | biostudies-literature

Chemoselective boronic ester synthesis by controlled speciation.

Project description:Control of boronic acid solution speciation is presented as a new strategy for the chemoselective synthesis of boronic esters. Manipulation of the solution equilibria within a cross-coupling milieu enables the formal homologation of aryl and alkenyl boronic acid pinacol esters. The generation of a new, reactive boronic ester in the presence of an active palladium catalyst also facilitates streamlined iterative catalytic C-C bond formation and provides a method for the controlled oligomerization of sp(2) -hybridized boronic esters.

| S-EPMC4501314 | biostudies-literature

Rosin-Based Epoxy Vitrimers with Dynamic Boronic Ester Bonds.

Project description:Rosin is an abundantly available natural product. In this paper, for the first time, a rosin derivative is employed as the main monomer for preparation of epoxy vitrimers to improve the mechanical properties of vitrimers. Novel epoxy vitrimer networks with dynamic reversible covalent boronic ester bonds are constructed by a reaction between thiols in 2,2'-(1,4-phenylene)-bis (4-mercaptan-1,3,2-dioxaborolane) (BDB) as a curing agent and epoxy groups in the rosin derivative. The rosin-based epoxy vitrimer networks are fully characterized by Fourier transform infrared spectroscopy (FTIR), an equilibrium swelling experiment, and dynamic mechanical analysis (DMA). The obtained rosin-based epoxy vitrimers possess superior thermostability and good mechanical properties. Due to transesterification of boronic ester bonds, rosin epoxy vitrimer network topologies can be altered, giving welding, recycle, self-healing, and shape memory abilities to the fabricated polymer. Besides, the effects of treating time and temperature on welding capability is investigated, and it is found that the welding efficiency of the 20% C-FPAE sample is >93% after treatment for 12 h at 160 °C. Moreover, through a hot press, the pulverized samples of 20% C-FPAE can be reshaped several times and most mechanical properties are restored after reprocessing at 200 °C for 60 min. Finally, chemical degradation is researched for the rosin-based epoxy vitrimers.

| S-EPMC8512039 | biostudies-literature

Glycidol Fatty Acid Ester and 3-Monochloropropane-1,2-Diol Fatty Acid Ester in Commercially Prepared Foods.

Project description:Glycidyl fatty acid esters (GEs), which are the main pollutant in processed oils, are potential mutagens or carcinogens. 3-Monochloropropane-1,2-diol fatty acid esters (3-MCPDEs) are also well-known food processing contaminants. 3-MCPDEs are believed to be a precursor to GEs in foodstuffs. In vivo, lipase breaks down the phosphate ester of GEs and 3-MCPDEs to produce glycidol and 3-MCPD, respectively, which are genotoxic carcinogens. Thus, it is important to determine human exposure to GEs and 3-MCPDEs through foodstuffs. There are only reports on the amount of GE and 3-MCPDE in cooking oils and cooked foods. The content in multiple types of foods that are actually on the market was not clarified. In this study, 48 commercially prepared foods were analyzed to identify other sources of exposure to GE and 3-MCPDE. All of them contained relatively high amounts of GEs and 3-MCPDEs. The correlation between GEs and 3-MCPDEs in individual foods was examined. There was a correlation between the amounts of GEs and 3-MCPDEs in the food products (r = 0.422, p < 0.005). This is the first report on the content in multiple types of commercially prepared foods that are actually on the market was clarified.

| S-EPMC8700650 | biostudies-literature

Simultaneous Disulfide and Boronic Acid Ester Exchange in Dynamic Combinatorial Libraries.

Project description:Dynamic combinatorial chemistry has emerged as a promising tool for the discovery of complex receptors in supramolecular chemistry. At the heart of dynamic combinatorial chemistry are the reversible reactions that enable the exchange of building blocks between library members in dynamic combinatorial libraries (DCLs) ensuring thermodynamic control over the system. If more than one reversible reaction operates in a single dynamic combinatorial library, the complexity of the system increases dramatically, and so does its possible applications. One can imagine two reversible reactions that operate simultaneously or two reversible reactions that operate independently. Both these scenarios have advantages and disadvantages. In this contribution, we show how disulfide exchange and boronic ester transesterification can function simultaneous in dynamic combinatorial libraries under appropriate conditions. We describe the detailed studies necessary to establish suitable reaction conditions and highlight the analytical techniques appropriate to study this type of system.

| S-EPMC4613285 | 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