Synthesis of perfluoroalkylated sugars catalyzed by rabbit muscle aldolase (RAMA)

摘要

Perfluoroalkyl iodides [RfI: Cl(CF2)(4)I, Cl(CF2)(6)I, C8F17I] react with acrolein diethyl acetal catalyzed by sulfinatodehalogenation reagents to produce 2-iodo-3-(perfluoroalkyl)propanal diethyl acetal 1, which is converted into (E)-3-(perfluoroalkyl)acrolein diethyl acetals 2 on treatment by base (KOH-MeOH). 3-Perfluoroalkyl-D-glyceraldehyde diethyl acetals 3 are produced through the asymmetric dihydroxylation (AD) of compound 2. Then 3 are easily hydrolyzed to 3-perfluoroalkyl-D-glyceraldehydes 4, which could react with DHAP catalyzed by RAMA and further acid phosphatase to form 6-C-perfluoroalkyl-D-fructose, which is a novel sugar and surfactant. [References: 23]