Biocatalytic Synthesis of Two-Photon Active Resveratrol Oligomer

Abstract

Resveratrol (3,5,4′ trihydroxy trans-stilbene) is a plant based phenolic compound. Enzymatic oligomerization of trans-resveratrol using horseradish peroxidase followed by characterization of the oligomer is presented. The oligomerization reaction was monitored using UV-Visible absorption and fluorescence spectroscopies. The oligomer exhibits strong two-photon-induced fluorescence. Computational modeling using spin-density calculations was performed to investigate the most probable reaction sites and the nature of products formed in the oligomerization process.

Keywords:

• Resveratrol
• oligo-resveratrol
• Horseradish Peroxidase
• biocatalysis
• Enzymatic
• computational modeling
• two-photon-fluorescence

Acknowledgments

Financial support from US Army Research Lab and National Science Foundation is gratefully acknowledged. We acknowledge Ms. Sheila Tripathy, Mr. Sharavanan Balasubramaniam, Dr. Ferdinando Bruno and Dr. Ryan Bouldin for their support and advice. Part of the research was performed while L.L. held a National Research Council Senior Research Associateship at US Army Natick Soldier Research, Development and Engineering Center.

Dedicated to the memory of Professor Sukant K. Tripathy.