Glycosylated hydroxytryptophan in a mussel adhesive protein from Perna viridis

J Biol Chem. 2009 Aug 28;284(35):23344-52. doi: 10.1074/jbc.M109.022517. Epub 2009 Jul 7.

Abstract

The 3,4-dihydroxyphenyl-l-alanine (Dopa)-containing proteins of mussel byssus play a critical role in wet adhesion and have inspired versatile new synthetic strategies for adhesives and coatings. Apparently, however, not all mussel adhesive proteins are beholden to Dopa chemistry. The cDNA-deduced sequence of Pvfp-1, a highly aromatic and redox active byssal coating protein in the green mussel Perna viridis, suggests that Dopa may be replaced by a post-translational modification of tryptophan. The N-terminal tryptophan-rich domain of Pvfp-1 contains 42 decapeptide repeats with the consensus sequences ATPKPW(1)TAW(2)K and APPPAW(1)TAW(2)K. A small collagen domain (18 Gly-X-Y repeats) is also present. Tandem mass spectrometry of isolated tryptic decapeptides has detected both C(2)-hexosylated tryptophan (W(1)) and C(2)-hexosylated hydroxytryptophan (W(2)), the latter of which is redox active. The UV absorbance spectrum of W(2) is consistent with 7-hydroxytryptophan, which represents an intriguing new theme for bioinspired opportunistic wet adhesion.

Publication types

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

MeSH terms

  • 5-Hydroxytryptophan / metabolism*
  • Amino Acid Sequence
  • Animals
  • Consensus Sequence
  • Glycosylation
  • Molecular Sequence Data
  • Perna / chemistry
  • Perna / genetics
  • Perna / metabolism*
  • Protein Structure, Tertiary
  • Proteins / chemistry*
  • Proteins / genetics
  • Proteins / metabolism*
  • Sequence Alignment

Substances

  • Proteins
  • adhesive protein, mussel
  • 5-Hydroxytryptophan