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Open AccessCommunication
Bioengineering 2014, 1(4), 246-259; doi:10.3390/bioengineering1040246

Biocatalytic Synthesis of Fluorescent Conjugated Indole Oligomers

1
Department of Natural and Applied Sciences, Bentley University, Waltham, MA 02452, USA
2
Department of Plastics Engineering, University of Massachusetts, Lowell, MA 01854, USA
3
Center for Advanced Materials, University of Massachusetts, Lowell, MA 01854, USA
4
Department of Physics, University of Massachusetts, Lowell, MA 01854, USA
*
Author to whom correspondence should be addressed.
Received: 28 July 2014 / Revised: 18 September 2014 / Accepted: 27 November 2014 / Published: 3 December 2014
(This article belongs to the Special Issue Biofabrication)
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Abstract

Fluorescent conjugated materials exhibiting reasonable biocompatibility that are capable of interacting with biological molecules are of interest for bio-sensing and imaging applications. Traditional approaches do not allow for the synthesis of conjugated materials in the presence of biologically relevant substrates. Further conjugated polymers synthesized using conventional methods are doped and not fluorescent. Here we explore the possibility of synthesizing fluorescent oligomers of indole using enzymes as catalyst under mild conditions. The peroxidase catalyzed coupling reaction presented here creates a photoluminescent material that allows for direct utilization (without purification and separation of the dopant) in biosensing applications. The polymerization reaction proceeds smoothly in just deionized water and ethanol. Monitoring of the absorption and fluorescence spectra over one hour shows that the concentration of both absorbing and emitting species grows steadily over time. The presence of anionic buffers and templates is shown to effectively retard the development of light emitting species and instead leads to the formation of an electrically doped conjugated polymer. Structural characterization through FTIR and 1H-NMR analysis suggests that the oligomer is coupled through the 2 and 3 positions on the indole ring. View Full-Text
Keywords: polyindole; indole oligomer; biocatalyic; oxidoreductase; enzymatic polymerization; soybean peroxidase polyindole; indole oligomer; biocatalyic; oxidoreductase; enzymatic polymerization; soybean peroxidase
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Bouldin, R.M.; Singh, A.; Magaletta, M.; Connor, S.; Kumar, J.; Nagarajan, R. Biocatalytic Synthesis of Fluorescent Conjugated Indole Oligomers. Bioengineering 2014, 1, 246-259.

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