Spirolactones of tyrosine: synthesis and reaction with nucleophiles (CROSBI ID 114048)
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Podaci o odgovornosti
Hutinec, Antun ; Ziogas, Athanassios ; Medhat El-Mobayed ; Rieker, Anton
engleski
Spirolactones of tyrosine: synthesis and reaction with nucleophiles
Several quinonoidal spirolactones (1-oxaspiro[4, 5]deca-6, 9-diene-2, 8-diones) 12 have been synthesized chemically or electrochemically by oxidation of the corresponding tyrosine phenols 3. The spirolactones are of considerable value in peptide chemistry, because they react as active esters with amino acid esters to give dipeptides. In the latter, the side chain of the tyrosine moiety is present as a quinol (4-hydroxycyclohexa-2, 5-dien-1-one) system, which can be reduced to the genuine tyrosyl dipeptide. Unsubstituted spirolactones also react as active esters but give dipeptides only in modest yields.
Spirolactones of Tyrosine
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