Abstract
γ-Butyrobetaine hydroxylase (BBOX) is a 2-oxoglutarate dependent oxygenase that catalyzes the final hydroxylation step in the biosynthesis of carnitine. BBOX was shown to catalyze the oxidative desymmetrization of achiral N,N-dialkyl piperidine-4-carboxylates to give products with two or three stereogenic centers.
Highlights
Abstract: g-Butyrobetaine hydroxylase (BBOX) is a 2-oxoglutarate dependent oxygenase that catalyzes the final hydroxylation step in the biosynthesis of carnitine
The screen led to the identification of N,N-dimethyl-piperidine-4-carboxylic acid acid (1) as a potential human butyrobetaine hydroxylase (BBOX) substrate (Figure S2)
NMR analysis of the reaction product resulting from the incubation of N,N-dimethyl-piperidine-4-carboxylic acid (1) with BBOX revealed the formation of a single alcohol product: 3-hydroxy-N,N-dimethyl-piperidine-4-carboxylic acid (2; Scheme 1 B, Figure 1, and Figure S3)
Summary
Abstract: g-Butyrobetaine hydroxylase (BBOX) is a 2-oxoglutarate dependent oxygenase that catalyzes the final hydroxylation step in the biosynthesis of carnitine. The screen led to the identification of N,N-dimethyl-piperidine-4-carboxylic acid acid (1) as a potential human BBOX substrate (Figure S2). NMR analysis of the reaction product resulting from the incubation of N,N-dimethyl-piperidine-4-carboxylic acid (1) with BBOX revealed the formation of a single alcohol product: 3-hydroxy-N,N-dimethyl-piperidine-4-carboxylic acid (2; Scheme 1 B, Figure 1, and Figure S3).
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