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Title: Alternative Reactivity of Leucine 5-Hydroxylase Using an Olefin-Containing Substrate to Construct a Substituted Piperidine Ring.
Applying enzymatic reactions to produce useful molecules is a central focus of chemical biology. Iron and 2-oxoglutarate (Fe/2OG) enzymes are found in all kingdoms of life and catalyze a broad array of oxidative transformations. Herein, we demonstrate that the activity of an Fe/2OG enzyme can be redirected when changing the targeted carbon hybridization from sp3 to sp2. During leucine 5-hydroxylase catalysis, installation of an olefin group onto the substrate redirects the Fe(IV)−oxo species reactivity from hydroxylation to asymmetric epoxidation. The resulting epoxide subsequently undergoes intramolecular cyclization to form the substituted piperidine, 2S,5S-hydroxypipecolic acid.
Authors:
; ; ; ; ; ; ;
Editors:
Booker, S
Award ID(s):
1845913
Publication Date:
NSF-PAR ID:
10217433
Journal Name:
Biochemistry
Volume:
59
Page Range or eLocation-ID:
1961-1965
ISSN:
1520-4995
Sponsoring Org:
National Science Foundation
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