Structural characterization of CYP260A1 from Sorangium cellulosum to investigate the 1α-hydroxylation of a mineralocorticoid

FEBS Lett. 2016 Dec;590(24):4638-4648. doi: 10.1002/1873-3468.12479. Epub 2016 Nov 23.

Abstract

In this study, we report the crystal structure of the cytochrome P450 CYP260A1 (PDB 5LIV) from the myxobacterium Sorangium cellulosum So ce56. In addition, we investigated the hydroxylation of 11-deoxycorticosterone by CYP260A1 by reconstituting the enzyme with the surrogate redox partners adrenodoxin and adrenodoxin reductase. The major product of this steroid conversion was identified as 1α-hydroxy-11-deoxycorticosterone, a novel Δ4 C-21 steroidal derivative. Furthermore, we docked the substrate into the crystal structure and replaced Ser326, the residue responsible for substrate orientation, with asparagine and observed that the mutant S326N displayed higher activity and selectivity for the formation of 1α-hydroxy-11-deoxycorticosterone compared to the wild-type CYP260A1. Thus, our findings highlight the usefulness of the obtained crystal structure of CYP260A1 in identifying biotechnologically more efficient reactions.

Keywords: P450; S326N; crystal structure of CYP260A1; mineralocorticoid; steroid hydroxylation.

Publication types

  • Letter

MeSH terms

  • Adrenodoxin / chemistry
  • Adrenodoxin / metabolism
  • Bacterial Proteins / chemistry*
  • Bacterial Proteins / genetics
  • Bacterial Proteins / metabolism
  • Crystallography, X-Ray
  • Cytochrome P-450 Enzyme System / chemistry*
  • Cytochrome P-450 Enzyme System / genetics
  • Cytochrome P-450 Enzyme System / metabolism
  • Desoxycorticosterone / chemistry*
  • Desoxycorticosterone / metabolism
  • Ferredoxin-NADP Reductase / genetics
  • Ferredoxin-NADP Reductase / metabolism
  • Gene Expression
  • Hydroxylation
  • Kinetics
  • Mineralocorticoids / chemistry*
  • Mineralocorticoids / metabolism
  • Molecular Docking Simulation
  • Mutation
  • Myxococcales / chemistry*
  • Myxococcales / enzymology
  • Oxidation-Reduction
  • Protein Domains
  • Protein Structure, Secondary
  • Recombinant Proteins / chemistry
  • Recombinant Proteins / genetics
  • Recombinant Proteins / metabolism
  • Structure-Activity Relationship
  • Substrate Specificity

Substances

  • Bacterial Proteins
  • Mineralocorticoids
  • Recombinant Proteins
  • Adrenodoxin
  • Desoxycorticosterone
  • Cytochrome P-450 Enzyme System
  • Ferredoxin-NADP Reductase