AIMS: The present study was carried out to assess the potential of Fusarium globulosum lipase (FGL) for chemoselective and regioselective biotransformations for the synthesis of industrially important organic compounds. METHODS AND RESULTS: Different acetylation/deacetylation reactions and ester synthesis reactions were carried out in organic media. Fusarium globulosum lipase showed exclusive selectivity for the acetylation of the alcoholic hydroxyl group over the phenolic hydroxyl group of the hydroxymethylated phenols and aryl alkyl ketones. This also led to the enantiomeric resolution of the aryl alkyl ketone. In contrast, the lipase showed reversed selectivity in deacetylation where it preferred the phenolic acetoxy group over the alcoholic acetoxy moiety of the peracetates of hydroxymethylated compounds. The enzyme also exhibited strict regioselection for deacetylation at the para position of the peracetate of an aryl alkyl ketone. In addition, the lipase also synthesized a variety of industrially important fatty acid esters of sugars, sugar alcohols, alcohols and ascorbic acid with high preference for middle-chain fatty acids. CONCLUSION: Fusarium globulosum lipase shows versatile catalytic potential in terms of chemo-, enantio- and regioselectivity and fatty acid specificity in carrying out a variety of industrially important biotransformations. SIGNIFICANCE AND IMPACT OF THE STUDY: The biocatalytic potential of FGL can thus be utilized for the synthesis and modification of different types of polyphenolic compounds and esters. These compounds find widespread uses as surfactants, bioactive analogues, antioxidants and flavour components in the food, detergent, pharmaceutical and cosmetic industries.
AIMS: The present study was carried out to assess the potential of Fusarium globulosum lipase (FGL) for chemoselective and regioselective biotransformations for the synthesis of industrially important organic compounds. METHODS AND RESULTS: Different acetylation/deacetylation reactions and ester synthesis reactions were carried out in organic media. Fusarium globulosum lipase showed exclusive selectivity for the acetylation of the alcoholic hydroxyl group over the phenolic hydroxyl group of the hydroxymethylated phenols and aryl alkyl ketones. This also led to the enantiomeric resolution of the aryl alkyl ketone. In contrast, the lipase showed reversed selectivity in deacetylation where it preferred the phenolic acetoxy group over the alcoholic acetoxy moiety of the peracetates of hydroxymethylated compounds. The enzyme also exhibited strict regioselection for deacetylation at the para position of the peracetate of an aryl alkyl ketone. In addition, the lipase also synthesized a variety of industrially important fatty acid esters of sugars, sugar alcohols, alcohols and ascorbic acid with high preference for middle-chain fatty acids. CONCLUSION: Fusarium globulosum lipase shows versatile catalytic potential in terms of chemo-, enantio- and regioselectivity and fatty acid specificity in carrying out a variety of industrially important biotransformations. SIGNIFICANCE AND IMPACT OF THE STUDY: The biocatalytic potential of FGL can thus be utilized for the synthesis and modification of different types of polyphenolic compounds and esters. These compounds find widespread uses as surfactants, bioactive analogues, antioxidants and flavour components in the food, detergent, pharmaceutical and cosmetic industries.