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
*Corresponding authors
aDepartment of Biochemical Engineering, University College London, Bernard Katz Building, Gordon Street, London, UK
bDepartment of Chemistry, University College London, Christopher-Ingold Building, 20 Gordon Street, London, UK
Green Chem., 2015,17, 852-855

DOI: 10.1039/C4GC02325K

Royal Society of Chemistry
image file: c4gc02325k-s1.tif
Scheme 1 Overview of the biocatalytic and non-enzymatic cascades presented in this work, including the ‘triangular’ cascade.
image file: c4gc02325k-u1.tif
image file: c4gc02325k-u2.tif
image file: c4gc02325k-s2.tif
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
  • Professor of Chemical Biology
  • Dept of Chemistry
  • Faculty of Maths & Physical Sciences
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 146

9 Research Activities


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.

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