One-pot triangular chemoenzymatic cascades for the syntheses of chiral alkaloids from dopamine

B. R. Lichman; E. D. Lamming; T. Pesnot; J. M. Smith; H. C. Hailes; J. M. Ward

doi:10.1039/C4GC02325K

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One-pot triangular chemoenzymatic cascades for the syntheses of chiral alkaloids from dopamine†

B. R. Lichman,

^a E. D. Lamming,^b T. Pesnot,^b J. M. Smith,^a H. C. Hailes*^b and J. M. Ward*^a

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* Corresponding authors

^a Department of Biochemical Engineering, University College London, Bernard Katz Building, Gordon Street, London, WC1H 0AH, UK
E-mail: j.ward@ucl.ac.uk

^b Department of Chemistry, University College London, Christopher-Ingold Building, 20 Gordon Street, London, WC1H 0AJ, UK
E-mail: h.c.hailes@ucl.ac.uk

Abstract

We describe novel chemoenzymatic routes to (S)-benzylisoquinoline and (S)-tetrahydroprotoberberine alkaloids using the enzymes transaminase (TAm) and norcoclaurine synthase (NCS) in a one-pot, one-substrate ‘triangular’ cascade. Employment of up to two C–C bond forming steps allows for the rapid generation of molecular complexity under mild conditions.

This article is part of the themed collection: 2015 most accessed Green Chemistry articles

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DOI: https://doi.org/10.1039/C4GC02325K
Article type: Communication
Submitted: 25 Pun 2014
Accepted: 12 Tsh 2014
First published: 18 Tsh 2014
This article is Open Access

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Green Chem., 2015,17, 852-855

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One-pot triangular chemoenzymatic cascades for the syntheses of chiral alkaloids from dopamine

B. R. Lichman, E. D. Lamming, T. Pesnot, J. M. Smith, H. C. Hailes and J. M. Ward, Green Chem., 2015, 17, 852 DOI: 10.1039/C4GC02325K

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One-pot triangular chemoenzymatic cascades for the syntheses of chiral alkaloids from dopamine†

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One-pot triangular chemoenzymatic cascades for the syntheses of chiral alkaloids from dopamine

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