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Issue 9, 2010
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An enzymatic, stereoselective synthesis of (S)-norcoclaurine

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Abstract

An efficient, stereoselective, green synthesis of (S)-norcoclaurine (higenamine) has been developed using the recombinant (S)-norcoclaurine synthase (NCS) enzyme, starting from the cheap tyrosine and dopamine substrates in a one-pot, two step process. Key steps in the biotransformation consist of the oxidative decarboxylation of tyrosine by stoichiometric amounts of sodium hypochlorite in order to generate 4-hydroxyphenylacetadehyde, followed by the addition of enzyme and dopamine substrate in the presence of ascorbate, a necessary ingredient in order to avoid oxidation of the catechol moiety. Quantitative extraction of the product from an aqueous solution was achieved by adsorption onto active charcoal dispersed in the reaction mixture. The optimized process afforded enantiomerically pure (S)-norcoclaurine (93%) in a yield higher than 80% and allowed good recovery of the enzyme for recycling. The process thus developed represents the first example of a green Pictet–Spengler synthesis, which may pave the way to novel strategies in benzylisoquinoline alkaloid synthesis.

Graphical abstract: An enzymatic, stereoselective synthesis of (S)-norcoclaurine

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Publication details

The article was received on 23 Apr 2010, accepted on 29 Jun 2010 and first published on 30 Jul 2010


Article type: Paper
DOI: 10.1039/C0GC00036A
Green Chem., 2010,12, 1623-1627

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    An enzymatic, stereoselective synthesis of (S)-norcoclaurine

    A. Bonamore, I. Rovardi, F. Gasparrini, P. Baiocco, M. Barba, C. Molinaro, B. Botta, A. Boffi and A. Macone, Green Chem., 2010, 12, 1623
    DOI: 10.1039/C0GC00036A

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