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Science. 2010 Jul 16;329(5989):309-13. doi: 10.1126/science.1190239.

Computational design of an enzyme catalyst for a stereoselective bimolecular Diels-Alder reaction.

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  • 1Department of Biochemistry, University of Washington, Seattle, WA 98195, USA.

Abstract

The Diels-Alder reaction is a cornerstone in organic synthesis, forming two carbon-carbon bonds and up to four new stereogenic centers in one step. No naturally occurring enzymes have been shown to catalyze bimolecular Diels-Alder reactions. We describe the de novo computational design and experimental characterization of enzymes catalyzing a bimolecular Diels-Alder reaction with high stereoselectivity and substrate specificity. X-ray crystallography confirms that the structure matches the design for the most active of the enzymes, and binding site substitutions reprogram the substrate specificity. Designed stereoselective catalysts for carbon-carbon bond-forming reactions should be broadly useful in synthetic chemistry.

Comment in

PMID:
20647463
[PubMed - indexed for MEDLINE]
PMCID:
PMC3241958
Free PMC Article

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