EC 1.14.13.246 - 4β-methylsterol monooxygenase

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IntEnz Enzyme Nomenclature
EC 1.14.13.246

Names

Accepted name:
4β-methylsterol monooxygenase
Other name:
sdmA (gene name)
Systematic name:
3β-hydroxy-4,4-dimethylsteroid,NADH:oxygen oxidoreductase (C-4mβ-hydroxylating)

Reactions

Comments:

Contains a Rieske [2Fe-2S] iron-sulfur cluster. This bacterial enzyme (SdmA) participates in the biosynthesis of bacterial sterols. Together with SdmB it forms an enzyme system that removes one methyl group from the C-4 position of 4,4-dimethylated steroid molecules. SdmA catalyses three successive oxidations of the C-4β methyl group, turning it into a carboxylate group; the second enzyme, SdmB, is a bifunctional enzyme that catalyses two different activities. As EC 1.1.1.417, 3β-hydroxysteroid-4β-carboxylate 3-dehydrogenase (decarboxylating), it catalyses an oxidative decarboxylation that results in reduction of the 3β-hydroxy group at the C-3 carbon to an oxo group. As EC 1.1.1.270, 3β-hydroxysteroid 3-dehydrogenase, it reduces the 3-oxo group back to a 3β-hydroxyl. Unlike the animal/fungal enzyme EC 1.14.18.9, 4α-methylsterol monooxygenase, and the plant enzymes EC 1.14.18.10, plant 4,4-dimethylsterol C-4α-methyl-monooxygenase, and EC 1.14.18.11, plant 4α-monomethylsterol monooxygenase, this enzyme acts preferentially on the 4β-methyl group. Since no epimerization of the remaining C-4α methyl group occurs, the enzyme can only remove one methyl group, leaving a 4α-monomethylated product. Known substrates include 4,4-dimethyl-5α-cholest-8-en-3β-ol and 14-demethyllanosterol.

Links to other databases

Enzymes and pathways: NC-IUBMB , BRENDA , ExplorEnz , ENZYME@ExPASy , KEGG , MetaCyc , UniPathway
Structural data: CSA , EC2PDB

References

  1. Lee, A. K., Banta, A. B., Wei, J. H., Kiemle, D. J., Feng, J., Giner, J. L., Welander, P. V.
    C-4 sterol demethylation enzymes distinguish bacterial and eukaryotic sterol synthesis.
    Proc. Natl. Acad. Sci. U.S.A. 115 : 5884-5889 (2018). [PMID: 29784781]

[EC 1.14.13.246 created 2019]