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Table 2 Applications of catalytic promiscuity for useful biotransformations

From: Enzyme promiscuity: using the dark side of enzyme specificity in white biotechnology

Biotransformations Substrate (s) Enzyme (s) References
Regio- and stereoselective reductions Diketones ADHs from Lactobacillus kefir, Rhodococcus ruber, Thermoanaerobacter etc. [66]
Reduction reaction Phenylacetaldoxime ADHs from Rhodococcus ruber, Ralstonia sp., Thermoanaerobacter etc. [67]
Aza-Diels-Alder reaction 4-chlorobenzaldehyde, cyclohexenone, 4-anisidine Hen egg white lysozyme (HEWL) [74]
Domino Knoevenagel/intramolecular transesterification Salicylaldehyde, ethyl acetoacetate Alkaline protease from Bacillus licheniformis (BLAP) [58]
Transesterification reaction Guaifenesin, vinyl acetate Penicillin G acylase [78]
Knoevenagel reaction Aromatic aldehyde, acetyl acetone/Ethyl acetoacetate Papain from Carica papaya latex [54]
Ugi reaction for peptide synthesis (MCR)* Aldehyde, amine, isocyanide Novozyme 435 (commercially available, immobilized Candida antarctica lipase B) [47]
Asymmetric aldol reaction Aromatic aldehyde, cyclic ketone Nuclease p1 from Penicillium citrinum [51]
Asymmetric aldol reaction Heterocyclic ketone, aromatic aldehyde Ficin from fig tree latex [53]
Synthesis of 4-thiazolidinones Aromatic aldehyde, benzyl amine, mercaptoacetic acid Trypsin from porcine pancreas [55]
Domino oxa-Michael/aldol condensations Salicylaldehyde, methyl vinyl ketone α-amylase from Bacillus subtilis [59]
Henry reaction 4-cyanobenzaldehyde, nitromethane Glucoamylase from Aspergillus niger (AnGA) [60]
Retro aldol and transamination reactions L-threonine and L-allo-threonine (for retro aldol reaction); D- and L-alanine(for transamination reaction) Alanine racemase from Tolypocladium inflatum [68]
Double Michael addition reaction Cyclohexane-1,3-dione and (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one D-amino acylase [69]
Enantioselective aldol reaction Isatin derivatives, cyclic ketones Nuclease p1 from Penicillium citrinum [50]
Synthesis of 2,4-disubstituted thiazoles (MCR)* Benzylamine, isobutyraldehyde, thioacetic acid, methyl 3-(dimethylamino)-2-isocyanoacrylate Porcine pancreatic lipase (PPL) [44]
Michael addition-cyclization cascade reaction Substituted benzalacetones and 1,3-cyclic diketones E.coli BioH esterase [52]
Synthesis of substituted 2H-chromemes (MCR)* Salicylaldehyde, acetophenone, methanol Porcine pancreatic lipase [79]
Baylis-Hillman reaction p-nitrobenzaldehyde and methyl vinyl ketone E.coli BioH esterase [80]
Biginelli reaction (MCR)* Urea, ethyl acetoacetate, vinyl acetate Trypsin from porcine pancreas [81]
  1. *stands for Multi-component reaction.