title: Efficient chemoenzymatic synthesis of 4-nitrophenyl β-d-apiofuranoside and its use in screening of β-d-apiofuranosidases.
abstract: 4-Nitrophenyl β-d-apiofuranoside as a chromogenic probe for detection of β-d-apiofuranosidase activity was prepared in 61% yield from 2,3-isopropylidene-α,β-d-apiofuranose through a sequence of five reactions. The synthesis involves one regioselective enzymatic step-benzoylation of primary hydroxyl of 2,3-isopropylidene-α,β-d-apiofuranose catalysed by Lipolase 100T and stereoselective β-d-apiofuranosylation of p-nitrophenol using BF3⋅OEt2/Et3N. The product was used for screening of β-d-apiofuranosidase activity in 61 samples of crude commercial enzymes and plant materials. Fifteen enzyme preparations originating from different strains of genera Aspergillus display β-d-apiofuranosidase activity. The highest activity was found in Rapidase AR 2000 (78.27 U/g) and lyophilized Viscozyme L (64,36 U/g).
authors.affiliation: Laboratory of Biocatalysis and Organic Synthesis, Institute of Chemistry, Slovak Academy of Sciences, SK-845 38 Bratislava, Slovakia.
authors.forename: Peter
authors.initials: P
authors.lastname: Kis
authors.affiliation: Laboratory of Biocatalysis and Organic Synthesis, Institute of Chemistry, Slovak Academy of Sciences, SK-845 38 Bratislava, Slovakia.
authors.forename: Elena
authors.initials: E
authors.lastname: Potocká
authors.affiliation: Laboratory of Biocatalysis and Organic Synthesis, Institute of Chemistry, Slovak Academy of Sciences, SK-845 38 Bratislava, Slovakia.
authors.forename: Vladimír
authors.initials: V
authors.lastname: Mastihuba
authors.affiliation: Laboratory of Biocatalysis and Organic Synthesis, Institute of Chemistry, Slovak Academy of Sciences, SK-845 38 Bratislava, Slovakia. Electronic address: chemjama@savba.sk.
authors.forename: Mária
authors.initials: M
authors.lastname: Mastihubová
mesh_terms: D060326:Chemistry Techniques, Synthetic; D057075:Enzyme Assays; D006026:Glycoside Hydrolases / Q000378:metabolism*; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: C000613685:4-nitrophenyl beta-D-apiofuranoside; D009005:Monosaccharides; D006026:Glycoside Hydrolases
keywords: 4-Nitrophenyl β-d-apiofuranoside; Aspergillus; β-d-Apiofuranosidase