Saturday, 14 February 2015

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 
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
1991PhDDoctor of Philosophy – Organic ChemistryUniversity of Cambridge
1987BABachelor of Arts – Chemistry and MetallurgyUniversity of Cambridge 146
9 Research Activities

Thursday, 5 February 2015

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


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.
 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
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/op500373e
Publication Date (Web): January 22, 2015
Copyright © 2015 American Chemical Society
*(H.-J.F.) E-mail:, *(M.G.H.)
Currently, ICSYNTH has assumed a place as a unique predictive tool for route design in Chemical Development in AZ. While it is finding valuable commercial application in our own and others’ hands, it remains a work in progress.
ICsynthInfoChem’s powerful synthesis planning tool now in Version 2.0. Read more …
InfoChem will be represented at the forthcoming ACS Meeting in San Diego. You will find Dr. Josef Eiblmaier, Dr. Valentina Eigner Pitto, and Dr. Peter Loew …
InfoChem’s ICSYNTH is a powerful computer aided synthesis design tool that enables chemists to generate synthetic pathways for a target molecule. The benefit is that ICSYNTH can facilitate innovation by stimulating ideas for alternative or novel synthetic routes that otherwise may not be considered. This may lead to improved route design, for example shorter pathways or more economical reaction modifications.
After inputting the target, users can select different synthetic strategies depending on requirements. ICSYNTH then automatically generates a multistep interactive synthesis tree – each node on the tree representing a precursor. The advantages are that the suggested reactions are based on, and linked to, published reactions (or their analogs) and the precursor availability is automatically checked in commercial catalogs. Users can modify the synthesis tree or select precursors for further analysis.
At the heart of ICSYNTH is an algorithmic chemical knowledge base of transform libraries that are automatically generated from reaction databases. The number of transform libraries is only limited by the availability of validated reaction databases.
In addition to retro synthesis design, ICSYNTH has a forward reaction prediction module that offers reactivity mapping for the target molecule.Version 2.0 of ICSYNTH was launched in April 2014. The completely re-designed user interface (based on JavaScript) and major improvements in the algorithm responsible of the precursor search are the main enhancements of Version 2.0. In addition the forward reaction prediction algorithm has been optimized. Click here to see a complete version history.


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Monday, 2 February 2015

Light-Controlled Release of Cyclodextrin

 thumbnail image: Light-Controlled Release of Cyclodextrin

Light-Controlled Release of Cyclodextrin

Photoswitch reversibly releases cyclodextrin from molecular axle

The fabrication of photocontrolled molecular machines is one of the significant topics in supramolecular chemistry. To date, a great number of artificial molecular machines with promising photophysical properties, such as molecular shuttles and molecular switches, have shown potential applications in chemical and biological fields.
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Trapping Radicals to Make Acylpyrroles

Trapping Radicals to Make Acylpyrroles


Radical processes usually feature mild reaction conditions and good functional group tolerance. However, they usually require hazardous reagents like organotin or azo compounds.

A convenient microwave-promoted synthesis under mild and non-toxic conditions
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