Abstract
BackgroundChiral furfuryl alcohols are important precursors for the synthesis of valuable functionalized pyranones such as the rare sugar L-rednose. However, the synthesis of enantiopure chiral biobased furfuryl alcohols remains scarce. In this work, we present a chemoenzymatic route toward enantiopure nitrogen-containing (R)- and (S)-3-acetamido-5-(1-hydroxylethyl)furan (3A5HEF) from chitin-derived N-acetyl-D-glucosamine (NAG).Findings3-Acetamido-5-acetylfuran (3A5AF) was obtained from NAG via ionic liquid/boric acid-catalyzed dehydration, in an isolated yield of approximately 31%. Carbonyl reductases from Streptomyces coelicolor (ScCR) and Bacillus sp. ECU0013 (YueD) were found to be good catalysts for asymmetric reduction of 3A5AF. Enantiocomplementary synthesis of (R)- and (S)-3A5HEF was implemented with the yields of up to > 99% and the enantiomeric excess (ee) values of > 99%. Besides, biocatalytic synthesis of (R)-3A5HEF was demonstrated on a preparative scale, with an isolated yield of 65%.ConclusionsA two-step process toward the chiral furfuryl alcohol was successfully developed by integrating chemical catalysis with enzyme catalysis, with excellent enantioselectivities. This work demonstrates the power of the combination of chemo- and biocatalysis for selective valorization of biobased furans.Graphic abstract
Highlights
Nitrogen-containing chemicals constitute a group of valuable substances that have found wide applications in pharmaceutical, agricultural chemical, polymer, chemical, and food industries
A two-step process toward the chiral furfuryl alcohol was successfully developed by integrating chemical catalysis with enzyme catalysis, with excellent enantioselectivities
Enzyme screening The chemically catalytic synthesis of 3A5AF was performed by combining ionic liquid [Bmim]Cl with boric acid under microwave irradiation, according to a previous method (Drover et al 2012)
Summary
Nitrogen-containing chemicals constitute a group of valuable substances that have found wide applications in pharmaceutical, agricultural chemical, polymer, chemical, and food industries. It has been reported that most of the best-selling drugs as well as all the top agrochemicals are N-containing chemicals (Chen et al 2016, 2020, 2021). Most of industrial N-containing chemicals are obtained by introducing the nitrogen element from NH3 and its derivatives into fossil-based intermediates via chemical transformations. The sustained prevalence of N-containing groups in many important chemicals has greatly driven the development of efficient and sustainable catalytic routes toward organonitrogen chemicals. Chiral furfuryl alcohols are important precursors for the synthesis of valuable functionalized pyranones such as the rare sugar L-rednose. The synthesis of enantiopure chiral biobased furfuryl alcohols remains scarce. We present a chemoenzymatic route toward enantiopure nitrogen-containing (R)- and (S)3-acetamido-5-(1-hydroxylethyl)furan (3A5HEF) from chitin-derived N-acetyl-D-glucosamine (NAG)
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