Chemoenzymatic access to enantiopure N-containing furfuryl alcohol from chitin-derived N-acetyl-D-glucosamine

Abstract Background Chiral furfuryl alcohols are important precursors for the synthesis of valuable functionalized pyranones such as rare sugar L-rednose. However, enantiopure chiral biobased remains scarce. In this work, we present a chemoenzymatic route toward nitrogen-containing ( R )- and S )-3-acetamido-5-(1-hydroxylethyl)furan (3A5HEF) from chitin-derived N-acetyl-D-glucosamine (NAG). Findings 3-Acetamido-5-acetylfuran (3A5AF) was obtained NAG via ionic liquid/boric acid-catalyzed dehydration, in an isolated yield approximately 31%. Carbonyl reductases Streptomyces coelicolor (ScCR) Bacillus sp. ECU0013 (YueD) were found to be good catalysts asymmetric reduction 3A5AF. Enantiocomplementary )-3A5HEF implemented with yields up > 99% enantiomeric excess (ee) values 99%. Besides, biocatalytic demonstrated on preparative scale, 65%. Conclusions A two-step process alcohol successfully developed by integrating chemical catalysis enzyme catalysis, excellent enantioselectivities. This work demonstrates power combination chemo- biocatalysis selective valorization furans. Graphic abstract