Insight into microwave irradiation and enzyme catalysis in enantioselective resolution of RS‐( ± )‐methyl mandelate

Abstract

BACKGROUND: Mandelic acid enantiomers are important chiral analogs used for the resolution of racemic alcohols and amines. R-(−)-mandelic acid is a precursor for the production of semi-synthetic penicillins and cephalosporins and also for the synthesis of various pharmaceuticals. Production of optically pure mandelic acid enantiomers is commercially significant. This work deals with the resolution of RS-(±)-methyl mandelate to produce optically pure R-(−)-mandelic acid in non-aqueous media via lipase-catalyzed hydrolysis under microwave irradiation.

Kinetics and mechanism of regioselective monoacetylation of 3-aryloxy-1,2-propandiols using immobilized Candida antarctica lipase

“…The production of 12 enantiomerically pure compounds has gained significant impor- 13 tance in chemical and pharmaceutical industry. Biocatalysts have 14 predominance due to their high chemo-, regio, enantio-selectivity 15 and exhibit high stability in organic reaction medium [5][6][7]. 16 Biocatalytic asymmetric synthesis offers great potential as an 17 alternative tool to chemical synthesis and provides a major path 18 for the synthesis of enantiomerically pure compounds through 19 kinetic resolution of racemic substrates or asymmetrization of 20 prochiral compounds [8][9][10][11][12][13][14].…”

“…Lipases are widely 42 present in different sources which include bacteria and fungi 43 and hence can be readily available for biotransformation of 44 interest. Lipases are suitable catalyst in terms of catalytic activity 45 and selectivity [33][34][35][36][37][38][39][40][41]. 46 The compounds containing 1,2-diol functional groups are of 47 great interest in the synthesis of pharmaceutical intermediates.…”

Easy preparation of enantiomerically enriched heteroaromatic alcohols through lipase-catalyzed acylation with succinic anhydride under unconventional activation

“…The microwave irradiation triggers the effect which cannot be procured by thermal heating, it leads to direct coupling of molecules by selective absorption of radiation by polar compounds, so the collision chance between enzyme and substrate molecules increased which might help to form enzyme-substrate complexes and the reaction rate was improved [51].…”

Synthesis of geranyl acetate by transesterification of geraniol with ethyl acetate over Candida antarctica lipase as catalyst in solvent‐free system

“…Enzymatic solvent‐free synthesis offers several advantages for the production of different chemicals with respect to high selectivity, improved recovery, and ease of purification, with the formation of little or no by‐products, and with less energy consumption. Several enzymes are used as biocatalysts, among which lipases are well studied because of their versatility . Lipase‐catalysed reactions (EC 3.1.1.3) reported in the literature include alcoholysis, aminolysis, epoxidation, esterification, peroxidation, transesterification, triacylglycerol hydrolysis, etc.…”