Optical and Electrochemical Detection of Saccharides with Poly(aniline-co-3-aminobenzeneboronic acid) Prepared from Enzymatic Polymerization

Abstract

Boronic acid-based sensors for saccharides have been developed via biocatalysis. The self-doped copolymer of poly(aniline-co-3-aminobenzeneboronic acid) [poly(aniline-co-AB)], with various mole ratios of two components, was synthesized by oxidative enzymatic polymerization using a natural biocatalyst such as horseradish peroxidase together with an anionic polyelectrolyte template (sulfonated polystyrene) under mild conditions (pH 4.5). Poly(aniline-co-AB), having an aniline boronic acid-to-aniline ratio of 1:2 on average, gave rise to a green doped polymer with absorption maxima at 745 nm. The potentiometric detection of saccharides using poly(aniline-co-AB) is presented. Characteristics of both transient and steady-state response associated with the complex formation of poly(aniline-co-AB) with various saccharides were monitored by UV-vis spectroscopy and cyclic voltammetry (CV). The results obtained from UV-vis spectroscopy and CV show that the sensitivity of enzymatically synthesized water-soluble poly(aniline-co-AB) for various saccharides was improved significantly compared to the chemically synthesized counterpart. A possible mechanism for the sensitive detection of sugar molecules by boronic acid is proposed on the basis of UV-vis and IR spectrophotometry, and four-point probe conductivity measurements.

Enzymatic oligomerization and polymerization of arylamines: state of the art and perspectives

“…Copolymerization is also a convenient route to functionalized PANI with versatile applicability. The enzymatic syntheses of aniline copolymers with other arylamines have only occasionally been explored (Akkara et al 1994b; Bruno et al 1995a, b; Huh et al 2007; Nabid et al 2010), while the enzymatic copolymerization of aniline with heterocyclic compounds was scarcely reported (Chen and Schuster 2013). …”

“…The self-doped copolymer poly(aniline- co -3-aminobenzeneboronic acid) with various molar ratios of aniline to 3-aminobenzeneboronic acid was synthesized by oxidative enzymatic polymerization using HRP/H 2 O 2 and a polyanionic template (SPS) at pH 4.5 (Huh et al 2007). A green emeraldine salt form of poly(aniline- co -3-aminobenzeneboronic acid) was obtained in the case of an aniline boronic acid to aniline ratio of 1:2.…”

Facile one-pot synthesis of fluorescent hyperbranched polymers for optical detection of glucose

“…Phenylboronic acid has been widely utilized for the design of chemosensors in the detection of saccharides over the past decades. [22][23][24][25][26] The covalent interactions between phenylbronic acid and the hydroxyl groups of saccharides (1,2-or 1,3-diols) lead to the formation of five-or sixmembered rings and allow bronic acid to be a sensitive detector for saccharides. [25][26][27][28] Figure 4 shows the fluorescent intensity curves vs. glucose concentration controlled at 0-0.8 mg/mL and the concentration of polymer kept at 0.5 wt%.…”

Enzyme Initiated Radical Polymerizations

“…In the absence of a suitable template aniline polymerizes with poor regioselectivity yielding complex, insoluble and non conducting polymers. However, e.g., in the presence of negatively charged PSS (and in the presence of protonated aniline, i.e., at suitable pHs) formation of the conducting emeraldine form is strongly favored (Figure 12) [27,[73][74][75][76][77][78][79].…”