TABLE 1.
Substrate specificity of recombinant CYP719B1
Enzyme assays were analyzed by LC-MS/MS. In the mass spectrum, products were sought that were substrate molecular ion minus 2 (phenol-coupling or methylenedioxy bridge formation); minus 14 (demethylation) and plus 16 (hydroxylation). The chemical structures are provided in supplemental Fig. S1.
| Substrate | Conversion kcat |
|---|---|
| % | |
| Isoquinoline alkaloids | |
| Cheilanthifoline | nda |
| (S)-Coclaurine | nd |
| Codeine | nd |
| (S)-Coreximine | nd |
| (R,S)-3'-Hydroxy-N-methylcoclaurine | nd |
| (R,S)–Isococlaurine | nd |
| (R,S)–Isoorientaline | nd |
| (R,S)-Laudanine | nd |
| (R,S)-Laudanosoline | nd |
| (R,S)-N-Methylcoclaurine | nd |
| (R,S)-4'-O-Methylcoclaurine | nd |
| (R,S)-4'-O-Methyllaudanosoline | nd |
| (S)-4'-O-Methyllaudanosoline | nd |
| (R,S)–6-O-Methyllaudanosoline | nd |
| Morphine | nd |
| (R,S)–Norcoclaurine | nd |
| (R,S)-Nororientaline | nd |
| (R)-Norprotosinomenine | nd |
| (S)-Norprotosinomenine | nd |
| (R)-Norreticuline | 8 |
| (S)-Norreticuline | nd |
| (R,S)-Orientaline | nd |
| Oripavine | nd |
| Papaverine | nd |
| (R,S)–Protosinomenine | nd |
| (R)-Reticuline | 100b |
| (S)-Reticuline | nd |
| Salutaridine | nd |
| (S)-Scoulerine | nd |
| (S)-Tetrahydrocolumbamine | nd |
| Thebaine | nd |
| Phenylpropanoids/flavonoids/coumarins | |
| Ferulic acid | nd |
| Isoeugenol | nd |
| 3-O-Methylquercitin | nd |
| Naringenin | nd |
| Scopoletin | nd |
| Sinapic acid | nd |
| Simple phenols | |
| Guaiacol | nd |
| 3-Methoxycatechol | nd |
| 3-Methoxytyramine | nd |
| Vanillic acid | nd |
a nd, not detected.
b100% activity is 1.64 min−1.