Carboxyl Formation from Methyl via Triple Hydroxylations by XiaM in Xiamycin A Biosynthesis

The P450 enzyme XiaM was identified as a candidate to form the C-24 carboxyl group in xiamycin A (1). Alteration of medium composition led to the discovery of four new compounds from the ΔxiaM and the ΔxiaK (encoding an aromatic ring hydroxylase) mutants. Biotransformation experiments revealed that...

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Veröffentlicht in:	Organic letters 2012-12, Vol.14 (24), p.6142-6145
Hauptverfasser:	Zhang, Qingbo, Li, Huixian, Li, Sumei, Zhu, Yiguang, Zhang, Guangtao, Zhang, Haibo, Zhang, Wenjun, Shi, Rong, Zhang, Changsheng
Format:	Artikel
Sprache:	eng
Schlagworte:	Aryl Hydrocarbon Hydroxylases Cytochrome P-450 CYP2B6 Cytochrome P-450 Enzyme System - metabolism Escherichia coli - genetics Escherichia coli - metabolism Hydroxylation Mixed Function Oxygenases - metabolism Oxidoreductases, N-Demethylating Sesquiterpenes - chemical synthesis Sesquiterpenes - chemistry Streptomyces - chemistry Streptomyces - genetics Streptomyces - metabolism
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Beschreibung
Zusammenfassung:	The P450 enzyme XiaM was identified as a candidate to form the C-24 carboxyl group in xiamycin A (1). Alteration of medium composition led to the discovery of four new compounds from the ΔxiaM and the ΔxiaK (encoding an aromatic ring hydroxylase) mutants. Biotransformation experiments revealed that XiaM was capable of converting a methyl group to a carboxyl group through diol and aldehyde intermediates.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol302782u