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. 2021 Nov 4;38(11):2100–2129. doi: 10.1039/d1np00032b

Reactive chemical features found in natural products.

Reactive chemical feature Structure Enzymatic route(s) to installation Genome mining efforts using reactive chemical feature biosynthetic enzymes
Enediyne graphic file with name d1np00032b-u1.jpg PKS16,17 Large scale genome mining18,19
β-Lactam graphic file with name d1np00032b-u2.jpg (1) β-Lactam synthetase (β-LS)20 Single genome mining24
(2) Carbapenam synthetase (CPS)21
(3) IPNS22
(4) Condensation domain23
β-Lactone graphic file with name d1np00032b-u3.jpg (1) β-Lactone synthetase25,26 Large scale genome mining26
(2) Thioesterase (TE)27
(3) Hydrolase28 Single genome mining29
Michael acceptor: α,β-unsaturated carbonyl graphic file with name d1np00032b-u4.jpg (1) Terpenes synthase30
(2) PKSs31
(3) Hybrid NRPS-PKS32
Epoxyketone graphic file with name d1np00032b-u5.jpg (1) Flavin-dependent decarboxylase–dehydrogenase–monooxygenase33,34 Large scale genome mining35
Epoxide graphic file with name d1np00032b-u6.jpg (1) P450 (epothilone)36 Single genome mining41
(2) Flavin-dependent epoxidases37 Single genome mining42
(3) Dioxygenases (epoxyquinones)38
(4) Non-heme iron-dependent epoxidases (fosfomycin)39,40
Aziridine graphic file with name d1np00032b-u7.jpg Unknown
Maleimide graphic file with name d1np00032b-u8.jpg (1) Flavin-dependent oxidase43
(2) PKS-NRPS44
Sulfonamide/sulfone graphic file with name d1np00032b-u9.jpg (1) Radical-forming, SO2 incorporating flavoprotein45
Furan graphic file with name d1np00032b-u10.jpg Terpene oxidation46 Large scale genome mining47
Disulfide graphic file with name d1np00032b-u11.jpg (1) FAD-dependent dithiol oxidase (holomycin, gliotoxin, FK228)48–50 Single genome mining52
(2) DUF-SH didomain51 Large scale genome mining53
Isothiocyanate graphic file with name d1np00032b-u12.jpg Putative isonitrile synthase54 Large scale genome mining54
Carbamate graphic file with name d1np00032b-u13.jpg Carbamoyltransferase55