Premium
Formation of dityrosine and other fluorescent amino acids by reaction of amino acids with lipid hydroperoxides
Author(s) -
Kikugawa Kiyomi,
Kato Tetsuta,
Hayasaka Akira
Publication year - 1991
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02535978
Subject(s) - chemistry , butylated hydroxytoluene , amino acid , tyrosine , fluorescence , biochemistry , antioxidant , organic chemistry , physics , quantum mechanics
Formation of fluorescence by the reaction of various amino acids with lipid hydroperoxides, i.e. , linoleic acid 13‐monohydroperoxide, methyl linoleate 13‐monohydroperoxide and phosphatidylcholine hydroperoxide, in the presence of methemoglobin was investigated. Two types of fluorescence were produced: fluorescent dityrosine (3,3′‐dityrosine) from tyrosine, and unidentified fluorophores with α‐ and ε‐amino groups of various amino acids. While the former was stable after treatment with borohydride, the latter fluorophores were readily destroyed. The rate of dityrosine formation was rapid, and the yield of dityrosine was dependent on the concentrations of tyrosine and the lipid hydroperoxides. Butylated hydroxytoluene and tocopherol inhibited the formation of dityrosine, but did not affect the formation of fluorophores on the amino groups. Dityrosine appears to be formed by radical reaction of the lipid hydroperoxides, while the other fluorophores seem to be created by nonradical mechanisms.