IntroductionBenzylisoquinoline alkaloids display various bioactivities and are therefore used for pharmaceutical applications. Probably the most well‐known compounds in this class are the narcotic analgesic morphine, the cough suppressant codeine, the muscle relaxant papaverine, and sanguinarine and berberine, the latter two showing antimicrobial activities. These compounds can be found as natural products in secondary metabolic pathways of plants thought to serve as self‐defense agents against animals, viruses, and bacteria. Their biosynthesis is achieved via sophisticated enzymatic pathways, starting from the amino acid tyrosine.Norcoclaurine synthase (NCS, EC 18.104.22.168) is one of the first enzymes located in these pathways, catalyzing a stereospecific Pictet–Spengler reaction between dopamine and 4‐hydroxyphenylacetaldehyde yielding the benzylisoquinoline (S)‐norcoclaurine (Figure ). The Pictet–Spengler reaction is enabled in nature by a handful of enzymes with different types of substrates. Additionally to the NCS, there is the strictosidine synthase, the salsolinol synthase, and McbB from Marinactinospora thermotolerans.The Pictet–Spengler reaction carried out by norcoclaurine synthase.Recently, the substrate scope of the NCS from Coptis japonica (CjNCS2) and from Thalictrum flavum (TfNCS) was elucidated and showed that a broad scope of aldehydes is accepted, while the number of possible amines is more restricted.The NCS reactions were typically carried out on small scale and with
Biotechnology Journal – Wiley
Published: Jan 1, 2018
Keywords: ; ; ; ;
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