alpha,beta-Dehydro-3,4-dihydroxyphenylalanine derivatives: rate and mechanism of formation.

@article{Rzepecki1991alphabetaDehydro34dihydroxyphenyl,
  title={alpha,beta-Dehydro-3,4-dihydroxyphenylalanine derivatives: rate and mechanism of formation.},
  author={L M Rzepecki and J Herbert Waite},
  journal={Archives of biochemistry and biophysics},
  year={1991},
  volume={285 1},
  pages={27-36}
}
The amino acid L-3,4-dihydroxyphenylalanine (DOPA), when present in the primary sequence of proteins, does not form melanin upon oxidation to the quinone, since its amine moiety participates in a peptide bond and cannot undergo internal cyclization. Instead, peptidyl DOPA quinone is available for other reactions. We have investigated the oxidation chemistry of a low molecular weight peptidyl DOPA analog, N-acetylDOPA ethyl ester (NAcDEE), and have shown that a major product of oxidation is an… CONTINUE READING

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