Table 1 Synthesis of cyanohydrins with DtHNL1.
From: Enzyme discovery beyond homology: a unique hydroxynitrile lyase in the Bet v1 superfamily
Entry | Substrate | 0.5 hours | 2 hours | 6 hours | 24 hours | |||||
|---|---|---|---|---|---|---|---|---|---|---|
→ | conv | ee | conv | ee | conv | ee | conv | ee | ||
Product | % | % | % | % | % | % | % | % | ||
1 | benzaldehyde → (2R)-2-hydroxy-2-phenylacetonitrile | DtHNL1 | 95.1 | 99.0 | 97.4 | 94.5 | 97.9 | 85.9 | 99.5 | 61.4 |
Control | −4.9 | – | 11.7 | 0.8 | 18.5 | 0.3 | 39.7 | 0.5 | ||
2 | 2-chlorobenzaldehyde → (2R)-2-(2-chlorophenyl)-2-hydroxyacetonitrile | DtHNL1 | 38.6 | 89.4 | 75.6 | 92.1 | 96.6 | 88.4 | 99.6 | 71.3 |
Control | 11.3 | −14.0 | 19.6 | −5.7 | 28.7 | −2.3 | 59.8 | −1.5 | ||
3 | 3-phenylpropanal → (2R)-2-hydroxy-4-phenylbutanenitrile | DtHNL1 | 50.9 | 45.8 | 84.8 | 48.3 | 94.5 | 48.1 | 93.2 | 48.0 |
Control | 18.0 | 0.4 | 36.3 | 0.2 | 53.0 | 0.0 | 80.2 | 0.2 | ||
4 | 3-phenylprop-2-enal → (2R)-2-hydroxy-4-phenylbut-3-enenitrile | DtHNL1 | 5.3 | 82.3 | 46.6 | 95.2 | 88.2 | 94.5 | 98.2 | 92.6 |
Control | −17.0 | – | −11.6 | – | −12.6 | – | −10.5 | – | ||
5 | furan-2-carbaldehyde → (2S)-furan-2-yl-hydroxyacetonitrile | DtHNL1 | 95.3 | 99.3 | 98.0 | 98.9 | 98.0 | 97.6 | 98.1 | 92.9 |
Control | 10.5 | 0.0 | 20.5 | 0.4 | 35.9 | 0.1 | 71.1 | −0.1 | ||
6 | 1-phenylethanone → 2-hydroxy-2-phenylpropanenitrile | DtHNL1 | 9.8 | n.d. | 17.3 | n.d. | 23.5 | n.d. | 22.3 | n.d. |
Control | 6.6 | – | 6.6 | – | 6.9 | – | 7.0 | – | ||
