Efficient chemoenzymatic synthesis of 4-nitrophenyl P-Dapiofuranoside and its use in screening of P-D-apiofuranosidases

4-Nitrophenyl beta-D-apiofuranoside as a chromogenic probe for detection of fi-n-apiofuranosidase activity was prepared in 61% yield from 2,3-isopropylidene-alpha-beta-u-apiofuranose through a sequence of five reactions. The synthesis involves one regioselective enzymatic step benzoylation of primary hydroxyl of 2,3-isopropylidene-alpha,beta-D-apiofuranose catalysed by Lipolase 100T and stereoselective beta-Dapiofuranosylation of p-nitrophenol using BF3 center dot OEt2/Et3N. The product was used for screening of fi-napiofuranosidase activity in 61 samples of crude commercial enzymes and plant materials. Fifteen enzyme preparations originating from different strains of genera Aspergillns display fi-n-apiofuranosidase activity. The highest activity was found in Rapidase AR 2000 (78.27 U/g) and lyophilized Viscozyme L (64,36 L/g). (C) 2016 Elsevier Ltd. All rights reserved.