Use of imine reductases (IREDs) for the production of a range of simple alkaloids from the corresponding imines.
| Product | IREDa | Conditions | Convb. [%] | ee [%] | Ref. |
|---|---|---|---|---|---|
|
Nh-IRED | 5 mM imine, 0.25 mg mL−1 IRED (purified enzyme), buffer not reported, 30 °C | 90 | 82 | 124a |
| IRED-B | 50 mM imine, 2 mg mL−1 IRED (crude cell-free preparation), buffer (pH 7.5), 30 °C | 98 | >99 | 124b | |
| (R)-IRED GF3587 | 25 mM imine, whole cells expressing IRED (OD600 = 30), buffer (pH 7.0), 30 °C | >98 (90 isol.) | >98 | 123 | |
| (S)-coniine (ent-218) | Bc-IRED | 5 mM imine, 0.25 mg mL−1 IRED (purified enzyme), buffer not reported, 30 °C | 57 | 35 | 124a |
| IRED-G | 50 mM imine, 2 mg mL−1 IRED (crude cell-free preparation), buffer (pH 6.0), 30 °C | 75 | 70 | 124b | |
|
(S)-IRED GF3546 | 5 mM imine, whole cells expressing IRED (OD600 = 30), buffer (pH 7.0), 30 °C | 92 | >98 | 125a |
| Ao-IRED (wt) | 5 mM imine, 0.4 mg mL−1 IRED (purified enzyme), buffer (pH 7.5), 30 °C | 50 | 79 | 125c | |
| IRED-M | 10 mM imine, 2 mg mL−1 IRED (crude cell-free preparation), buffer (pH 7.5), 30 °C | >99 | >99 | 125e | |
| Sn-IRED | 100 mM imine, 10 mg mL−1 IRED (crude cell-free preparation), buffer (pH 7.0), 30 °C | >99 (76 isol.) | >99 | 125d | |
| (R)-salsolidine (ent-174) | Ao-IRED (Y179A) | 5 mM imine, 0.4 mg mL−1 IRED (purified enzyme), buffer (pH 7.5), 30 °C | 15 | >99 | 125c |
|
(S)-IRED GF3546 | 5 mM imine, whole cells expressing IRED (OD600 = 30), buffer (pH 7.0), 30 °C | >98 | >98 | 125a |
| IRED-M | 10 mM imine, 2 mg mL−1 IRED (crude cell-free preparation), buffer (pH 7.5), 30 °C | 92 | >99 | 125e | |
| Sa-IRED | 20 mM, 0.08 U mL−1 IRED (crude cell-free preparation), buffer (pH 7.0) | 91 | 99 | 125b | |
| (R)-eleagnine (ent-175) | Ao-IRED (wt) | 5 mM imine, 0.4 mg mL−1 IRED (purified enzyme), buffer (pH 7.5), 30 °C | 5 | >99 | 125c |
| IRED-D | 10 mM imine, 2 mg mL−1 IRED (crude cell-free preparation), buffer (pH 7.5), 30 °C | 27 | 78 | 125e | |
|
(S)-IRED GF3546 | 5 mM imine, whole cells expressing IRED (OD600 = 30), buffer (pH 7.0), 30 °C | 50 | >98 | 125a |
| Ao-IRED (wt) | 5 mM imine, 0.4 mg mL−1 IRED (purified enzyme), buffer (pH 7.5), 30 °C | 15 | 79 | 125c | |
| IRED-L | 10 mM imine, 2 mg mL−1 IRED (crude cell-free preparation), buffer (pH 7.5), 30 °C | 88 | >99 | 125e | |
| (R)-leptaflorine (ent-219) | Ao-IRED (N241A) | 5 mM imine, 0.4 mg mL−1 IRED (purified enzyme), buffer (pH 7.5), 30 °C | 96 | 60 | 125c |
a
The IRED abbreviations are adopted from the original research articles and refer to the enzymes from the following source organisms: (R)-IRED GF3587, Streptomyces sp. GF3587; (S)-IRED GF3546, Streptomyces sp. GF3546; Ao-IRED, Amycolatopsis orientalis; Bc-IRED, Bacillus cereus BAG3X2; Nh-IRED, Nocardiopsis halophila; Sa-IRED, Streptomyces aurantiacus JA 4570; Sn-IRED, Stackebrandtia nassauensis; IRED-B, Streptomyces kanamyceticus; IRED-D, Mesorhizobium sp. L2C089B000; IRED-G, Streptomyces rimosus ATCC 10970; IRED-L, Nocardia brasiliensis ATCC 700358; IRED-M, Saccharothrix espanaensis ATCC 51144.
b
Conversion according to GC or HPLC analysis. The values in parentheses are isolated yields of preparative-scale transformations.