Enzymatic Protecting Group Techniques

A Novel Alkaline Esterase fromSporosarcinasp. nov. Strain eSP04 Catalyzing the Hydrolysis of a Wide Variety of Aryl-carboxylic Acid Esters

“…17,18) Aryl-carboxylesterases, however, have many potential applications in various fields. They are attractive biocatalysts for the production of various aromas, fragrances, 19,20) and preservatives, 17,18) for the selective removal of protecting groups, 21,22) and in the field of health [23][24][25][26] as well as being potentially beneficial for the environment. It is thus of great interest to obtain a new arylcarboxylesterase with broad or unusual substrate specificities.…”

Simple method for fast deprotection of nucleosides by triethylamine-catalyzed methanolysis of acetates in aqueous medium

“…Therefore, multi-step synthesis frequently requires the introduction of protective groups and their subsequent removal. [10][11][12][13] Typical methods for removing the acetate groups in acetylated nucleosides rely on the use of methanolic ammonia, [14][15][16] metal alkoxides, [16][17][18] and hydrolytic enzymes, 19 often in good yields. Although all of the above procedures offer certain benefits, they also suffer from drawbacks such as long reaction times, high costs, the use of unstable or noxious reagents, harmful conditions, and the need for special safety precautions, which represent major disadvantages due to environmental concerns.…”

Optimisation of the lipase-catalysed preparation of a nucleoside prodrug model using an experimental design methodology

“…In the field of nucleosides, the power of biocatalysis is well documented [9][10] . Biotransformations catalysed by hydrolytic enzymes provide convenient methods to achieve regioselective reactions in the sugar moiety of nucleosides.…”

“…In addition to the usefulness of the described and reviewed enzymatic regioselective acylation and alkoxycarbonylation of nucleosides [9][10] , the hydrolase-catalysed deacylation of nucleosides has also been studied, mainly through enzymatic hydrolysis of peracylated deoxynucleosides [11][12][13][14][15] and ribonucleosides 14,16,17 . Taking into account the excellent performance of Candida antarctica B lipase in organic syntheses 18 , and the regioselectivity displayed by this biocatalysts towards the 5' hydroxyl of nucleosides in reactions of acylation and alkoxycarbonylation [7][8][9][10][14][15][16] , over the last years we have been studying the Candida antarctica B lipasecatalysed alcoholysis of peracylated ribonucleosides. This biotransformation has proved to be a simple and convenient access to 2´, 3´-di-O-acylribonucleosides [19][20][21] , which can be considered as prodrug models of nucleosides.…”