| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1371487 | Bioorganic & Medicinal Chemistry Letters | 2012 | 4 Pages |
Abstract
γ-Butyrobetaine hydroxylase (BBOX) is a 2-oxoglutarate and Fe(II)-dependent oxygenase that catalyses the final step of l-carnitine biosynthesis in animals. BBOX catalyses the oxidation of 3-(2,2,2-trimethylhydrazinium)propionate (THP), a clinically used BBOX inhibitor, to form multiple products including 3-amino-4-(methyamino)butanoic acid (AMBA), which is proposed to be formed via a Stevens type rearrangement mechanism. We report the synthesis of AMBA and confirm that it is a product of the BBOX catalysed oxidation of THP. AMBA reacts with formaldehyde, which is produced enzymatically by BBOX, to give a cyclic adduct.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Luc Henry, Ivanhoe K.H. Leung, Timothy D.W. Claridge, Christopher J. Schofield,