α,β-Dehydro-Dopa: A Hidden Participant in Mussel Adhesion

We investigated the oxidation chemistry of a low-molecular weight analogue of peptidyl-Dopa, namely Nacetyl-Dopa ethyl ester, by cyclic voltammetry and UV−vis spectrophotometry

Razieh Mirshafian

2016

Scholarcy highlights

  • Both acidic and alkaline pH regimes are relevant to mussel adhesion
  • We investigated the oxidation chemistry of a low-molecular weight analogue of peptidyl-Dopa, namely Nacetyl-Dopa ethyl ester, by cyclic voltammetry and UV−vis spectrophotometry
  • D was purified for chemical characterization by mass spectrometry and UV−vis spectrophotometry
  • The catecholic functionality of peptidyl-Dopa can no longer be assumed to disappear upon oxidation of Dopa to Dopa-quinone at pH 7−8
  • This study reveals that despite formation of transient Dopa-quinone during the two-electron oxidation by periodate, a tautomer known as dehydro-Dopa predominates in solution
  • Quartz crystal microbalance measurements show that dehydro-Dopa has an adsorption capacity 20 times higher than that of Dopa on TiO2 surfaces
  • A better understanding of the role of dehydro-Dopa in adhesion will provide the basis for designing tunable synthetic adhesives for underwater and medical applications

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