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] |