IUBMB Enzyme Nomenclature

EC 1.14.13.70

Accepted name: sterol 14α-demethylase

Reaction: a 14α-methylsteroid + 3 O2 + 3 NADPH + 3 H+ = a Δ14-steroid + formate + 3 NADP+ + 4 H2O

For diagram of reaction click here.

Glossary: obtusifoliol = 4α,14α-dimethyl-5α-ergosta-8,24(28)-dien-3β-ol or 4α,14α-dimethyl-24-methylene-5α-cholesta-8-en-3β-ol

Other name(s): obtusufoliol 14-demethylase; lanosterol 14-demethylase; lanosterol 14α-demethylase; sterol 14-demethylase

Systematic name: sterol,NADPH:oxygen oxidoreductase (14-methyl cleaving)

Comments: This heme-thiolate (P-450) enzyme acts on a range of steroids with a 14α-methyl group, such as obtusifoliol and lanosterol. The enzyme catalyses two successive hydroxylations of the 14α-methyl group, followed by elimination as formate, leaving a 14(15) double bond.

Links to other databases: BRENDA, EXPASY, KEGG, Metacyc, PDB, CAS registry number: 60063-87-8

References:

1. Bak, S., Kahn, R.A., Olsen, C.E. and Halkier, B.A. Cloning and expression in Escherichia coli of the obtusifoliol 14α-demethylase of Sorghum bicolor (L.) Moench, a cytochrome P450 orthologous to the sterol 14α-demethylases (CYP51) from fungi and mammals. Plant J. 11 (1997) 191-201. [PMID: 9076987]

2. Aoyama, Y. and Yoshida, Y. Different substrate specificities of lanosterol 14α-demethylase (P450-14DM) of Saccharomyces cerevisiae and rat liver of 24-methylene-24,25-dihydrolanosterol and 24,25-dihydrolanosterol. Biochem. Biophys. Res. Commun. 178 (1991) 1064-1071. [PMID: 1872829]

3. Aoyama, Y. and Yoshida, Y. The 4β-methyl group of substrate does not affect the activity of lanosterol 14α-demethylase (P45014DM) of yeast: differences between the substrate recognition by yeast and plant sterol 14α-demethylases. Biochem. Biophys. Res. Commun. 183 (1992) 1266-1272. [PMID: 1567403]

4. Alexander, K., Akhtar, M., Boar, R.B., McGhie, J.F. and Barton, D.H.R. The removal of the 32-carbon atom as formic acid in cholesterol biosynthesis. J. Chem. Soc. Chem. Commun. (1972) 383-385.

[EC 1.14.13.70 created 2001, modified 2013]


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