Journal
TETRAHEDRON
Volume 70, Issue 27-28, Pages 4245-4249Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2014.03.008
Keywords
Artificial metalloenzyme; Manganese; C-H functionalization; Epoxidation; Biocatalysis
Categories
Funding
- David and Lucile Packard Foundation
- NSF under the CCI Center for Selective C-H Functionalization [CHE-1205646]
- NIH Chemistry and Biology Interface Training Grant [T32 GM008720]
- NSF instrumentation grant [CHE-1048528]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1205646, 1048528] Funding Source: National Science Foundation
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New catalysts for non-directed hydrocarbon functionalization have great potential in organic synthesis. We hypothesized that incorporating a Mn-terpyridine cofactor into a protein scaffold would lead to artificial metalloenzymes (ArMs) in which the selectivity of the Mn cofactor could be controlled by the protein scaffold. We designed and synthesized a maleimide-substituted Mn-terpyridine cofactor and demonstrated that this cofactor could be incorporated into two different scaffold proteins to generate the desired ArMs. The structure and reactivity of one of these ArMs was explored, and the broad oxygenation capability of the Mn-terpyridine catalyst was maintained, providing a robust platform for optimization of ArMs for selective hydrocarbon functionalization. (C) 2014 Elsevier Ltd. All rights reserved.
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