Oxidative phenol coupling—tyrosine dimers and libraries containing tyrosyl peptide dimers

The principles of phenol oxidation are outlined and summarized. Various procedures were used to dimerize tyrosine derivatives, especially linear tripeptides and cyclohexapeptides, via cross-linking of their phenolic side-chains. The coupling was performed by potassium hexacyanoferrate(III), phenylio...

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Bibliographic Details
Published inTetrahedron Vol. 57; no. 2; pp. 353 - 364
Main Authors Eickhoff, Holger, Jung, Günther, Rieker, Anton
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 07.01.2001
Elsevier
Subjects
amino acids and derivatives
biaryls
Chemistry
Chemistry, Organic
oxidation
peptide analogues/mimetics
Physical Sciences
Science & Technology
oxidation
biaryls
peptide analogues/mimetics
amino acids and derivatives
AMARYLLIDACEAE ALKALOIDS
HINDERED PHENOLS
CATALYZED OXIDATION
REAKTIONEN MIT AROXYLEN
AMINO-ACIDS
DURCH PHENOLDEHYDRIERUNG
HYDROXY-DIPHENYLATHERN
HYPERVALENT IODINE(III) REAGENT
ELECTROCHEMICAL OXIDATIONS
ANODIC-OXIDATION
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Summary:The principles of phenol oxidation are outlined and summarized. Various procedures were used to dimerize tyrosine derivatives, especially linear tripeptides and cyclohexapeptides, via cross-linking of their phenolic side-chains. The coupling was performed by potassium hexacyanoferrate(III), phenyliodine(III)-bis(trifluoroacetate), vanadium(V)-oxyfluoride or horseradish peroxidase. The individual dityrosine and isodityrosine derivatives obtained in preparative scale, as well as the peptide-dimer libraries generated, were characterized by HPLC and electrospray ionization mass spectrometry. Further analyses were carried out by NMR spectroscopy, fluorescence spectroscopy and gas chromatography.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(00)00942-X