Crystal structures of substrate-free and retinoic acid-bound cyanobacterial cytochrome P450 CYP120A1

Biochemistry. 2008 Jun 24;47(25):6552-9. doi: 10.1021/bi800328s.

Abstract

The crystal structures of substrate-free and all-trans-retinoic acid-bound CYP120A1 from Synechocystis sp. PCC 6803 were determined at 2.4 and 2.1 A resolution, respectively, representing the first structural characterization of a cyanobacterial P450. Features of CYP120A1 not observed in other P450 structures include an aromatic ladder flanking the channel leading to the active site and a triple-glycine motif within SRS5. Using spectroscopic methods, CYP120A1 is shown to bind 13-cis-retinoic acid, 9-cis-retinoic acid, and retinal with high affinity and dissociation constants of less than 1 microM. Metabolism of retinoic acid by CYP120A1 suggests that CYP120A1 hydroxylates a variety of retinoid derivatives in vivo. On the basis of the retinoic acid-bound CYP120A1 crystal structure, we propose that either carbon 2 or the methyl groups (C16 or C17) of the beta-ionone ring are modified by CYP120A1.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alitretinoin
  • Bacterial Proteins / chemistry*
  • Bacterial Proteins / metabolism
  • Binding Sites
  • Catalytic Domain
  • Crystallography, X-Ray
  • Cytochrome P-450 Enzyme System / chemistry*
  • Cytochrome P-450 Enzyme System / metabolism
  • Hydroxylation
  • Isotretinoin / chemistry
  • Isotretinoin / metabolism
  • Models, Molecular
  • Protein Binding
  • Protein Conformation
  • Protein Structure, Secondary
  • Protein Structure, Tertiary
  • Retinaldehyde / chemistry
  • Retinaldehyde / metabolism
  • Substrate Specificity
  • Synechocystis / enzymology*
  • Tretinoin / chemistry*
  • Tretinoin / metabolism

Substances

  • Bacterial Proteins
  • Alitretinoin
  • Tretinoin
  • Cytochrome P-450 Enzyme System
  • Isotretinoin
  • Retinaldehyde

Associated data

  • PDB/2VE3
  • PDB/2VE4