Linked Life Data

1846730

Source:http://linkedlifedata.com/resource/pubmed/id/1846730

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
1
pubmed:dateCreated
1991-3-6
pubmed:abstractText
Proteins containing the post-translationally modified amino acid L-3,4-dihydroxyphenylalanine (DOPA) undergo autosclerotization as a means of assuring cohesive resilience in many structural matrices found in nature. To explore the chemical mechanism of sclerotization, we examined the oxidation products of relatively simple analogs of a peptidyl DOPA residue, such as N-acetylDOPA ethyl ester and N-acetyldopamide, together with those of several oligopeptides. Oxidation, induced by either of two catecholoxidases or by sodium periodate, resulted in the Lewis base catalyzed formation of derivatives of the unusual amino acid 3,4-dihydroxy-alpha,beta-dehydroDOPA (delta DOPA). The N-acetyl delta DOPA ethyl ester representative of this group of derivatives was characterized by NMR and uv spectroscopy. A variety of peptides developed analogous uv spectra upon oxidation. A similar reaction was observed upon oxidation of 3,4-dihydroxyphenylpropanoic (dihydrocaffeic) acid, but not after oxidation of N-acetyldopamine. Evidence is presented that this conversion is the result of a rearrangement of the DOPA quinone moiety to its delta DOPA tautomer, and that this tautomerization can be a dominant fate for peptidyl DOPA quinone, provided a Lewis base catalyst is available and competing reactions are minimized. Formation of delta DOPA in natural or synthetic polymers would increase the variety of crosslinks available to sclerotizing matrices. delta DOPA has been found in naturally occurring oligopeptides isolated by other workers from several marine species.
pubmed:grant
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Feb
pubmed:issn
0003-9861
pubmed:author
pubmed:issnType
Print
pubmed:day
15
pubmed:volume
285
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
17-26
pubmed:dateRevised
2007-11-14
pubmed:meshHeading
pubmed:year
1991
pubmed:articleTitle
alpha,beta-Dehydro-3,4-dihydroxyphenylalanine derivatives: potential schlerotization intermediates in natural composite materials.
pubmed:affiliation
College of Marine Studies, University of Delaware, Lewes 19958.
pubmed:publicationType
Journal Article, Research Support, U.S. Gov't, P.H.S., Research Support, U.S. Gov't, Non-P.H.S.