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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.