Biocatalytic carbohydrate modification using lipase from Stutzerimonas stutzeri : From regioselective hydrolysis to glycolipid synthesis

Abstract

Selective carbohydrate functionalization remains one of the major challenges in synthetic chemistry owing to the presence of multiple hydroxyl groups with similar reactivity. Among the available biocatalysts, lipases have emerged as valuable tools for the regioselective modification of carbohydrates under mild and sustainable reaction conditions. Within this enzyme family, the lipase from Stutzerimonas stutzeri (LipSS) has attracted increasing attention because of its remarkable regioselectivity, broad solvent tolerance and compatibility with immobilization and process-intensification strategies. This review provides a critical overview of the current state of the art of LipSS-mediated carbohydrate transformations, with particular emphasis on regioselective hydrolysis of peracetylated sugars and the synthesis of sugar fatty acid esters. The structural and catalytic features responsible for its performance are discussed together with advances in enzyme immobilization, continuous-flow biocatalysis and the implementation of sustainable reaction media and alternative activation technologies. Whenever possible, the performance of LipSS is critically compared with that of other lipases commonly employed in carbohydrate chemistry in order to identify its main advantages, current limitations and potential application niches. Overall, the available evidence indicates that LipSS represents a versatile platform biocatalyst for sustainable carbohydrate functionalization. Although challenges related to large-scale implementation, catalyst production and process economics remain, recent advances in immobilization, reactor design and process intensification provide promising opportunities for the future development of efficient and environmentally friendly biocatalytic processes.