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Publication Details
AFRICAN RESEARCH NEXUS
SHINING A SPOTLIGHT ON AFRICAN RESEARCH
biochemistry, genetics and molecular biology
Crotonase catalysis enables flexible production of functionalized prolines and carbapenams
Journal of the American Chemical Society, Volume 134, No. 1, Year 2012
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Description
The biocatalytic versatility of wildtype and engineered carboxymethylproline synthases (CMPSs) is demonstrated by the preparation of functionalized 5-carboxymethylproline derivatives methylated at C-2, C-3, C-4, or C-5 of the proline ring from appropriately substituted amino acid aldehydes and malonyl-coenzyme A. Notably, compounds with a quaternary center (at C-2 or C-5) were prepared in a stereoselective fashion by engineered CMPSs. The substituted-5-carboxymethyl-prolines were converted into the corresponding bicyclic β-lactams using a carbapenam synthetase. The results demonstrate the utility of the crotonase superfamily enzymes for stereoselective biocatalysis, the amenability of carbapenem biosynthesis pathways to engineering for the production of new bicyclic β-lactam derivatives, and the potential of engineered biocatalysts for the production of quaternary centers. © 2011 American Chemical Society.
Authors & Co-Authors
Hamed, Refaat B.
United Kingdom, Oxford
University of Oxford
Egypt, Asyut
Faculty of Pharmacy
Henry, Luc
United Kingdom, Oxford
University of Oxford
Gomez-Castellanos, J. Ruben
United Kingdom, Oxford
University of Oxford
Mecinović, Jasmin
United Kingdom, Oxford
University of Oxford
Ducho, Christian
United Kingdom, Oxford
University of Oxford
Sorensen, John L.
United Kingdom, Oxford
University of Oxford
Claridge, Timothy D.W.
United Kingdom, Oxford
University of Oxford
Schofield, Christopher J.
United Kingdom, Oxford
University of Oxford
Statistics
Citations: 27
Authors: 8
Affiliations: 2
Identifiers
Doi:
10.1021/ja208318d
ISSN:
00027863
e-ISSN:
15205126