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

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

Green Chem., 2015, 17,852-855
DOI: 10.1039/C4GC02325K, Communication

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

*Corresponding authors

^aDepartment of Biochemical Engineering, University College London, Bernard Katz Building, Gordon Street, London, UK

E-mail: j.ward@ucl.ac.uk

^bDepartment of Chemistry, University College London, Christopher-Ingold Building, 20 Gordon Street, London, UK

E-mail: h.c.hailes@ucl.ac.uk

Green Chem., 2015,17, 852-855

DOI: 10.1039/C4GC02325K

http://pubs.rsc.org/en/Content/ArticleLanding/2015/GC/C4GC02325K?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

http://pubs.rsc.org/en/content/articlehtml/2015/gc/c4gc02325k

	Scheme 1 Overview of the biocatalytic and non-enzymatic cascades presented in this work, including the ‘triangular’ cascade.

	Scheme 2 One-pot chemoenzymatic synthesis of (S)-4 and (S)-5. Reaction conditions: (a) 20 mM 2, 10 mM sodium pyruvate, 500 μg mL−1 NCS and 20% v.v−1 CV2025 lysate, 50 mM HEPES pH 7.5, 37 °C, 3 h. (b) 40 mM formaldehyde, 1 M sodium phosphate, pH 6, 30 min, 37 °C.

Prof Helen Hailes

h.c.hailes@ucl.ac.uk

Appointment

• Professor of Chemical Biology
• Dept of Chemistry
• Faculty of Maths & Physical Sciences

Research Groups

• Industrial Biotechnology (BiCE)
• Institute of Biomedical Engineering (IBME)
• Institute of Structural & Molecular Biology, UCL/Birkbeck
• UCL Centre for Chemical Biology

Research Themes

• Synthetic Biology

Research Summary

Research activity in our group is focused on the use of synthetic organic chemistry to probe and solve biological problems. Current projects include the use of water as a reaction solvent and the use of catalytic and biocatalytic synthetic strategies. Also novel kinase inhibitors, cytosine-based hydrogen-bonding polymers and new lipid design for use in a ternary gene delivery vector.

Academic Background

1991	PhD	Doctor of Philosophy – Organic Chemistry	University of Cambridge
1987	BA	Bachelor of Arts – Chemistry and Metallurgy	University of Cambridge

publications..total 146

https://iris.ucl.ac.uk/iris/browse/profile?upi=HCHAI24

9 Research Activities

Status

• BiCE
• Calixarenes and Tuberculosis Therapies

  Active
• Chemoenzymatic and Biocatalytic Synthesis of Aminodiols (BiCE Project)

  Active
• Design and Synthesis of Novel Hydrogen Bonding Arrays

  Active
• Non-Viral Gene Therapy

  Active
• Organic Synthesis in Water

  Active
• Synthetic Biology

  Active
• The Synthesis of Novel Signaling Molecules

  Active
• The synthesis of PI 3-kinase and PKB activators and inhibitors

  Active

  UCL LONDON

Route Design in the 21st Century: The ICSYNTH Software Tool as an Idea Generator for Synthesis Prediction

New Drug Approvals

The new computer-aided synthesis design tool ICSYNTH has been evaluated by comparing its performance in predicting new ideas for route design to that of historical brainstorm results on a series of commercial pharmaceutical targets, as well as literature data. Examples of its output as an idea generator are described, and the conclusion is that it adds appreciable value to the performance of the professional drug research and development chemist team.

Anders Bøgevig^‡, Hans-Jürgen Federsel^*†,Fernando Huerta^‡, Michael G. Hutchings^*§, Hans Kraut^§, Thomas Langer^†, Peter Löw^§, Christoph Oppawsky^§, Tobias Rein^‡, and Heinz Saller^§

^† Chemical Development, AstraZeneca R&D, Silk Road Business Park, Macclesfield, SK10 2NA Cheshire, U.K.

^‡Chemnotia AB, Forskargatan 20 J, 151 36 Södertälje,Sweden

^§InfoChem GmbH, Landsberger Straße 408/V, D-81241 München, Germany

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