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

Tomohiro Michitaka,Toru Imai,Akihito Hashidzume

doi:10.3390/polym9110549

Abstract

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.

Highlights

IntroductionCarbohydrates are ubiquitous in our life and very important biological materials [1,2]
Carbohydrates are ubiquitous in our life and very important biological materials [1,2].Carbohydrates can be divided into three categories based on their molecular weight; (1) low molecular weight saccharides, e.g., monosaccharides and disaccharides, (2) oligosaccharides, and (3) polysaccharides
Low molecular weight saccharides are utilized as energy source for living organisms, and oligosaccharides exhibit a number of physiological activities

Summary

Introduction

Carbohydrates are ubiquitous in our life and very important biological materials [1,2]. Carbohydrates can be divided into three categories based on their molecular weight; (1) low molecular weight saccharides, e.g., monosaccharides and disaccharides, (2) oligosaccharides, and (3) polysaccharides. Low molecular weight saccharides are utilized as energy source for living organisms, and oligosaccharides exhibit a number of physiological activities. Carbohydrates used in biological systems are synthesized by enzymatic reactions [1,2]. Synthesis of carbohydrates in a non-enzymatic way has been an important subject of investigation [3,4,5,6]. Synthesis of monosaccharides from starting materials containing one or two carbon atoms is still remaining as a challenging subject because monosaccharides possess a number of chiral centers to be controlled [7,8]

Methods

Results

Conclusion