Chemo-enzymatic protocol converts chitin into a nitrogen-containing furan derivative, 3-acetamido-5-acetylfuran

Abstract

In this study, efficient production of the platform chemical 3-acetamido-5-acetylfuran (3A5AF) from chitin resources via a chemo-enzymatic protocol was investigated. Initially, chitinolytic enzyme was used to convert chitin into N-acetyl glucosamine (GlcNAc) using an affinity adsorption–enzymatic reaction integrated approach. Then, the obtained GlcNAc was used to produce 3A5AF using screened ammonium thiocyanate (NH4SCN) as the catalyst. The optimal conditions for converting GlcNAc into 3A5AF were determined at a temperature of 180 °C, solvent of DMAc, a molar ratio of GlcNAc to NH4SCN of 2:1, addition of CaCl2·2H2O, a molar ratio of GlcNAc to CaCl2·2H2O of 1:1 and a reaction time of 10 min, resulting in 3A5AF with a molar yield of 56.66%. The NH4SCN showed good recyclability within five cycles. Furthermore, upon scaling up of the 3A5AF preparation, a good yield was still maintained. Additionally, 99% pure 3A5AF needle-shaped crystals were obtained with 34 wt% yield by crystallisation purification. This new chemo-enzymatic protocol provides a good option to convert chitin resources into 3A5AF.