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γ-Butyrobetaine hydroxylase catalyses a Stevens type rearrangement.

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 ...

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Publication status:
Published

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Publisher copy:
10.1016/j.bmcl.2012.06.024

Authors


Claridge, TD More by this author
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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Journal:
Bioorganic and medicinal chemistry letters
Volume:
22
Issue:
15
Pages:
4975-4978
Publication date:
2012-08-05
DOI:
EISSN:
1464-3405
ISSN:
0960-894X
URN:
uuid:2ec9ff77-0522-4140-aac3-0dcc3e6b5a6a
Source identifiers:
341304
Local pid:
pubs:341304

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