Lipase-catalyzed synthesis of polyhydroxyalkyl furans from unprotected sugars and malononitrile

Abstract

BackgroundPolyhydroxyalkyl furans are important bioactive compounds that have been extensively studied in organic chemistry. In this work, a green and chemoselective process for the synthesis of polyhydroxyalkyl furans from unprotected sugars and malononitrile was developed. ResultsUnder optimal conditions (sugar (1 mmol), malononitrile (1 mmol), water (1 mL), Novozym 435 (200 U,13.2 mg), 60 °C, 6 h), high isolated yields of polyhydroxyalkyl furans (79 %–92 %) could be obtained when Novozym 435 was used as the catalyst, and no by-product was found in this system. Moreover, 76 % yield of polyhydroxyalkyl furan could be obtained even after six cycles. Thus, Novozym 435 exhibits satisfactory chemoselectivity and good reusability in this reaction. ConclusionThis enzymatic method demonstrates the great potential for the synthesis of polyhydroxyalkyl furans and extends the application of enzyme catalytic promiscuity in organic synthesis.