Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Formose reaction controlled by boronic acid compounds.

ABSTRACT: Formose reactions were carried out in the presence of low molecular weight and macromolecular boronic acid compounds, i.e., sodium phenylboronate (SPB) and a copolymer of sodium 4-vinylphenylboronate with sodium 4-styrenesulfonate (pVPB/NaSS), respectively. The boronic acid compounds provided different selectivities; sugars of a small carbon number were formed favorably in the presence of SPB, whereas sugar alcohols of a larger carbon number were formed preferably in the presence of pVPB/NaSS.

SUBMITTER: Imai T

PROVIDER: S-EPMC5238582 | biostudies-literature | 2016

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Formose reaction controlled by boronic acid compounds.

Imai Toru T Michitaka Tomohiro T Hashidzume Akihito A

Beilstein journal of organic chemistry 20161208

Formose reactions were carried out in the presence of low molecular weight and macromolecular boronic acid compounds, i.e., sodium phenylboronate (SPB) and a copolymer of sodium 4-vinylphenylboronate with sodium 4-styrenesulfonate (pVPB/NaSS), respectively. The boronic acid compounds provided different selectivities; sugars of a small carbon number were formed favorably in the presence of SPB, whereas sugar alcohols of a larger carbon number were formed preferably in the presence of pVPB/NaSS. ...[more]

PMID: 28144337

Similar Datasets

Formose Reaction Controlled by a Copolymer of N,N-Dimethylacrylamide and 4-Vinylphenylboronic Acid.

Project description:The formose reaction is an oligomerization of formaldehyde under basic conditions, which produces a complicated mixture of monosaccharides and sugar alcohols. Selective formation of useful monosaccharides by the formose reaction has been an important challenge. In this study, we have investigated the formose reaction controlled by N,N-dimethylacrylamide/4-vinylphenylboronic acid copolymer (pDMA/VBA) and phenylboronic acid (PBA) because boronic acid compounds form esters with polyols, e.g., monosaccharides and sugar alcohols. We obtained time⁻conversion data in the presence of these boronic acid compounds, and characterized the products by liquid chromatography-mass spectroscopy and NMR measurements. pDMA/VBA and PBA decelerated the formose reaction because of the formation of boronic acid esters with products. It is noteworthy that the formose reaction in the presence of pDMA/VBA and PBA formed favorably six- and seven-carbon branched monosaccharides and sugar alcohols.

| S-EPMC6418552 | biostudies-literature

Formose reaction accelerated in aerosol-OT reverse micelles.

Project description:The formose reaction in reverse micelles of aerosol-OT (AOT), triton X-100 (TX), and hexadecyltrimethylammonium bromide (CTAB) was investigated. Time-conversion data have indicated that the interfacial water layer of AOT reverse micelles is a medium that accelerates formation of glycolaldehyde in the formose reaction. The 13C NMR spectra for the products of the formose reaction using formaldehyde-13C as starting material are indicative of the formation of ethylene glycol as a major product.

| S-EPMC5238542 | biostudies-literature

The Messy Alkaline Formose Reaction and Its Link to Metabolism.

Project description:Sugars are essential for the formation of genetic elements such as RNA and as an energy/food source. Thus, the formose reaction, which autocatalytically generates a multitude of sugars from formaldehyde, has been viewed as a potentially important prebiotic source of biomolecules at the origins of life. When analyzing our formose solutions we find that many of the chemical species are simple carboxylic acids, including α-hydroxy acids, associated with metabolism. In this work we posit that the study of the formose reaction, under alkaline conditions and moderate hydrothermal temperatures, should not be solely focused on sugars for genetic materials, but should focus on the origins of metabolism (via metabolic molecules) as well.

| S-EPMC7460143 | biostudies-literature

Linked strategy for the production of fuels via formose reaction.

Project description:Formose reaction converts formaldehyde to carbohydrates. We found that formose reaction can be used linking the biomass gasification with the aqueous-phase processing (APP) to produce liquid transportation fuel in three steps. First, formaldehyde from syn-gas was converted to triose. This was followed by aldol condensation and dehydration to 4-hydroxymethylfurfural (4-HMF). Finally, 4-HMF was hydrogenated to produce 2,4-dimethylfuran (2,4-DMF) or C(9)-C(15) branched-chain alkanes as liquid transportation fuels. In the linked strategy, high energy-consuming pretreatment as well as expensive and polluting hydrolysis of biomass were omitted, but the high energy recovery of APP was inherited. In addition, the hexoketoses via formose reaction could be converted to HMFs directly without isomerization. A potential platform molecule 4-HMF was formed simultaneously in APP.

| S-EPMC3566532 | biostudies-other

Development and Elucidation of a Novel Fluorescent Boron-Sensor for the Analysis of Boronic Acid-Containing Compounds.

Project description:Novel boron-containing drugs have recently been suggested as a new class of pharmaceuticals. However, the majority of current boron-detection techniques require expensive facilities and/or tedious pretreatment methods. Thus, to develop a novel and convenient detection method for boron-based pharmaceuticals, imine-type boron-chelating-ligands were previously synthesized for use in a fluorescent sensor for boronic acid containing compounds. However, the fluorescence quantum yield of the imine-type sensor was particularly low, and the sensor was easily decomposed in aqueous media. Thus, in this paper, we report the development of a novel, convenient, and stable fluorescent boron-sensor based on O- and N-chelation (i.e., 2-(pyridine-2yl)phenol), and a corresponding method for the quantitative and qualitative detection of boronic acid-containing compounds using this commercially available sensor is presented.

| S-EPMC5677422 | biostudies-literature

2,4-Difluoro-phenyl-boronic acid.

Project description:The mol-ecular structure of the title compound, C(6)H(5)BF(2)O(2), is essentially planar (mean deviation = 0.019?Å), indicating electronic delocalization between the dihydroxy-boryl group and the aromatic ring. In the crystal structure, inversion dimers linked by two O-H?O hydrogen bonds arise. An intra-molecular O-H?F hydrogen bond reinforces the conformation and the same H atom is also involved in an inter-molecular O-H?F link, leading to mol-ecular sheets in the crystal.

| S-EPMC2967960 | biostudies-literature

2,4-Dibutoxy-phenyl-boronic acid.

Project description:In the crystal of the title compound, C(14)H(23)BO(4), centrosymmetric dimers linked by pairs of O-H?O hydrogen bonds occur. The dimers are linked via C-H?O contacts, generating a two-dimensional array parallel to (12). These are inter-connected by weak O-H?O hydrogen bonds, as well as C-H?? inter-actions.

| S-EPMC2969364 | biostudies-literature

(4-Carbamoylphen-yl)boronic acid.

Project description:In the title compound, C(7)H(8)BNO(3), the mol-ecule lies on an inversion center leading to a statistical disorder of the B(OH)(2) and CONH(2) groups. In the crystal structure, mol-ecules are linked by N-H?O and O-H?O hydrogen bonds, forming sheets parallel to the bc plane. The B(OH)(2) and CONH(2) groups are twisted out of the mean plane of the benzene ring by 23.9?(5) and 24.6?(6)°, respectively.

| S-EPMC2979401 | biostudies-literature

Click with a boronic acid handle: a neighboring group-assisted click reaction that allows ready secondary functionalization.

Project description:The feasibility of a neighboring boronic acid-facilitated facile condensation of an aldehyde is described. This reaction is bio-orthogonal, complete at room temperature within minutes, and suitable for bioconjugation chemistry. The boronic acid group serves the dual purpose of catalyzing the condensation reaction and being a handle for secondary functionalization.

| S-EPMC4603419 | biostudies-literature

Scope of the two-step, one-pot palladium-catalyzed borylation/Suzuki cross-coupling reaction utilizing bis-boronic acid.

Project description:The use of bis-boronic acid for the direct synthesis of boronic acids has greatly facilitated the two-step, one-pot borylation/Suzuki cross-coupling reaction between aryl and heteroaryl halides. With use of Buchwald's second-generation XPhos preformed catalyst, high yields of cross-coupled products were obtained for most substrates. The method also allows an efficient two-step, one-pot synthesis, providing access to three distinct cross-coupled products after column chromatography. The method also provides a rapid and convenient route to teraryl compounds.

| S-EPMC3465529 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

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