BIO-H-BORROW SIGNED
Biocatalytic Amine Synthesis via Hydrogen Borrowing
Total Cost €
0EC-Contrib. €
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Project "BIO-H-BORROW" data sheet
The following table provides information about the project.
| Coordinator |
THE UNIVERSITY OF MANCHESTER
Organization address contact info |
| Coordinator Country | United Kingdom [UK] |
| Total cost | 2˙337˙548 € |
| EC max contribution | 2˙337˙548 € (100%) |
| Programme |
1. H2020-EU.1.1. (EXCELLENT SCIENCE - European Research Council (ERC)) |
| Code Call | ERC-2016-ADG |
| Funding Scheme | ERC-ADG |
| Starting year | 2017 |
| Duration (year-month-day) | from 2017-06-01 to 2022-05-31 |
Partnership
Take a look of project's partnership.
| # | ||||
|---|---|---|---|---|
| 1 | THE UNIVERSITY OF MANCHESTER | UK (MANCHESTER) | coordinator | 2˙337˙548.00 |
Map
Project objective
Amine containing compounds are ubiquitous in everyday life and find applications ranging from polymers to pharmaceuticals. The vast majority of amines are synthetic and manufactured on large scale which creates waste as well as requiring high temperatures and pressures. The increasing availability of biocatalysts, together with an understanding of how they can be used in organic synthesis (biocatalytic retrosynthesis), has stimulated chemists to consider new ways of making target molecules. In this context, the iterative construction of C-N bonds via biocatalytic hydrogen borrowing represents a powerful and unexplored way to synthesise a wide range of target amine molecules in an efficient manner. Hydrogen borrowing involves telescoping redox neutral reactions together using only catalytic amounts of hydrogen. In this project we will engineer the three key target biocatalysts (reductive aminase, amine dehydrogenase, alcohol dehydrogenase) required for biocatalytic hydrogen borrowing such that they possess the required regio-, chemo- and stereo-selectivity for practical application. Recently discovered reductive aminases (RedAms) and amine dehydrogenases (AmDHs) will be engineered for enantioselective coupling of alcohols (1o, 2o) with ammonia/amines (1o, 2o, 3o) under redox neutral conditions. Alcohol dehydrogenases will be engineered for low enantioselectivity. Hydrogen borrowing requires mutually compatible cofactors shared by two enzymes and in some cases will require redesign of cofactor specificity. Thereafter we shall develop conditions for the combined use of these biocatalysts under hydrogen borrowing conditions (catalytic NADH, NADPH), to enable the conversion of simple and sustainable feedstocks (alcohols) into amines using ammonia as the nitrogen source. The main deliverables of BIO-H-BORROW will be a set of novel engineered biocatalysts together with redox neutral cascades for the synthesis of amine products from inexpensive and renewable precursors.
Publications
| year | authors and title | journal | last update |
|---|---|---|---|
| 2019 |
Lei Wan, Rachel S. Heath, Bhavin Siritanaratkul, Clare F. Megarity, Adam J. Sills, Matthew P. Thompson, Nicholas J. Turner, Fraser A. Armstrong Enzyme-catalysed enantioselective oxidation of alcohols by air exploiting fast electrochemical nicotinamide cycling in electrode nanopores published pages: 4958-4963, ISSN: 1463-9262, DOI: 10.1039/c9gc01534e |
Green Chemistry 21/18 | 2020-02-06 |
| 2019 |
Fei-Fei Chen, Sebastian C. Cosgrove, William R. Birmingham, Juan Mangas-Sanchez, Joan Citoler, Matthew P. Thompson, Gao-Wei Zheng, Jian-He Xu, Nicholas J. Turner Enantioselective Synthesis of Chiral Vicinal Amino Alcohols Using Amine Dehydrogenases published pages: 11813-11818, ISSN: 2155-5435, DOI: 10.1021/acscatal.9b03889 |
ACS Catalysis 9/12 | 2020-02-06 |
| 2018 |
Vasco F. Batista, James L. Galman, Diana C. G. A. Pinto, Artur M. S. Silva, Nicholas J. Turner Monoamine Oxidase: Tunable Activity for Amine Resolution and Functionalization published pages: 11889-11907, ISSN: 2155-5435, DOI: 10.1021/acscatal.8b03525 |
ACS Catalysis 8/12 | 2020-02-06 |
| 2018 |
Paul N. Devine, Roger M. Howard, Rajesh Kumar, Matthew P. Thompson, Matthew D. Truppo, Nicholas J. Turner Extending the application of biocatalysis to meet the challenges of drug development published pages: 409-421, ISSN: 2397-3358, DOI: 10.1038/s41570-018-0055-1 |
Nature Reviews Chemistry 2/12 | 2020-02-06 |
| 2018 |
Godwin A. Aleku, Juan Mangas-Sanchez, Joan Citoler, Scott P. France, Sarah L. Montgomery, Rachel S. Heath, Matthew P. Thompson, Nicholas J. Turner Kinetic Resolution and Deracemization of Racemic Amines Using a Reductive Aminase published pages: 515-519, ISSN: 1867-3880, DOI: 10.1002/cctc.201701484 |
ChemCatChem 10/3 | 2020-02-06 |
| 2018 |
Matthew P. Thompson, Itziar Peñafiel, Sebastian C. Cosgrove, Nicholas J. Turner Biocatalysis Using Immobilized Enzymes in Continuous Flow for the Synthesis of Fine Chemicals published pages: 9-18, ISSN: 1083-6160, DOI: 10.1021/acs.oprd.8b00305 |
Organic Process Research & Development 23/1 | 2020-02-06 |
| 2019 |
Clare F. Megarity, Bhavin Siritanaratkul, Rachel S. Heath, Lei Wan, Giorgio Morello, Sarah R. FitzPatrick, Rosalind L. Booth, Adam J. Sills, Alexander W. Robertson, Jamie H. Warner, Nicholas J. Turner, Fraser A. Armstrong Electrocatalytic Volleyball: Rapid Nanoconfined Nicotinamide Cycling for Organic Synthesis in Electrode Pores published pages: 4948-4952, ISSN: 1433-7851, DOI: 10.1002/anie.201814370 |
Angewandte Chemie International Edition 58/15 | 2020-02-06 |
| 2018 |
Evaldas Klumbys, Ziga Zebec, Nicholas J. Weise, Nicholas J. Turner, Nigel S. Scrutton Bio-derived production of cinnamyl alcohol via a three step biocatalytic cascade and metabolic engineering published pages: 658-663, ISSN: 1463-9262, DOI: 10.1039/c7gc03325g |
Green Chemistry 20/3 | 2020-02-06 |
| 2018 |
Scott P. France, Roger M. Howard, Jeremy Steflik, Nicholas J. Weise, Juan Mangas-Sanchez, Sarah L. Montgomery, Robert Crook, Rajesh Kumar, Nicholas J. Turner Identification of Novel Bacterial Members of the Imine Reductase Enzyme Family that Perform Reductive Amination published pages: 510-514, ISSN: 1867-3880, DOI: 10.1002/cctc.201701408 |
ChemCatChem 10/3 | 2020-02-06 |
| 2019 |
Thomas W. Thorpe, Scott P. France, Shahed Hussain, James R. Marshall, Wojciech Zawodny, Juan Mangas-Sanchez, Sarah L. Montgomery, Roger M. Howard, David S. B. Daniels, Rajesh Kumar, Fabio Parmeggiani, Nicholas J. Turner One-Pot Biocatalytic Cascade Reduction of Cyclic Enimines for the Preparation of Diastereomerically Enriched N -Heterocycles published pages: 19208-19213, ISSN: 0002-7863, DOI: 10.1021/jacs.9b10053 |
Journal of the American Chemical Society 141/49 | 2020-02-06 |
| 2017 |
Scott P. France, Godwin A. Aleku, Mahima Sharma, Juan Mangas-Sanchez, Roger M. Howard, Jeremy Steflik, Rajesh Kumar, Ralph W. Adams, Iustina Slabu, Robert Crook, Gideon Grogan, Timothy W. Wallace, Nicholas J. Turner Biocatalytic Routes to Enantiomerically Enriched Dibenz[ c , e ]azepines published pages: 15795-15799, ISSN: 0044-8249, DOI: 10.1002/ange.201708453 |
Angewandte Chemie 129/49 | 2020-02-06 |
| 2018 |
Mahima Sharma, Juan Mangas-Sanchez, Scott P. France, Godwin A. Aleku, Sarah L. Montgomery, Jeremy I. Ramsden, Nicholas J. Turner, Gideon Grogan A Mechanism for Reductive Amination Catalyzed by Fungal Reductive Aminases published pages: 11534-11541, ISSN: 2155-5435, DOI: 10.1021/acscatal.8b03491 |
ACS Catalysis 8/12 | 2020-02-06 |
| 2017 |
Iustina Slabu, James L. Galman, Richard C. Lloyd, Nicholas J. Turner Discovery, Engineering, and Synthetic Application of Transaminase Biocatalysts published pages: 8263-8284, ISSN: 2155-5435, DOI: 10.1021/acscatal.7b02686 |
ACS Catalysis 7/12 | 2020-02-06 |
| 2018 |
James L. Galman, Iustina Slabu, Fabio Parmeggiani, Nicholas J. Turner Biomimetic synthesis of 2-substituted N-heterocycle alkaloids by one-pot hydrolysis, transamination and decarboxylative Mannich reaction published pages: 11316-11319, ISSN: 1359-7345, DOI: 10.1039/C8CC06759G |
Chemical Communications 54/80 | 2019-04-18 |
| 2018 |
Nicholas John Turner, Anthony Green, Jin Xu Chemo-enzymatic synthesis of pyrazines and pyrroles published pages: , ISSN: 1433-7851, DOI: 10.1002/anie.201810555 |
Angewandte Chemie International Edition | 2019-04-18 |
| 2019 |
Jeremy I. Ramsden, Rachel S. Heath, Sasha R. Derrington, Sarah L. Montgomery, Juan Mangas-Sanchez, Keith R. Mulholland, Nicholas J. Turner Biocatalytic N -Alkylation of Amines Using Either Primary Alcohols or Carboxylic Acids via Reductive Aminase Cascades published pages: 1201-1206, ISSN: 0002-7863, DOI: 10.1021/jacs.8b11561 |
Journal of the American Chemical Society 141/3 | 2019-02-28 |
| 2019 |
Matthew P. Thompson, Sasha R. Derrington, Rachel S. Heath, Joanne L. Porter, Juan Mangas-Sanchez, Paul N. Devine, Matthew D. Truppo, Nicholas J. Turner A generic platform for the immobilisation of engineered biocatalysts published pages: 327-334, ISSN: 0040-4020, DOI: 10.1016/j.tet.2018.12.004 |
Tetrahedron 75/3 | 2019-02-28 |
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