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Isolation of Cross‐Coupling Products in Model Studies on the Photochemical Modification of Proteins by Tiaprofenic Acid
Author(s) -
Angel Miranda Miguel,
PérezPrieto Julia,
Lahoz Agustin,
Morera Isabel M.,
Sarabia Zaideth,
MartínezMáñez Ramón,
Castell Jose V.
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199902)1999:2<497::aid-ejoc497>3.0.co;2-7
Subject(s) - chemistry , coupling (piping) , isolation (microbiology) , photochemistry , combinatorial chemistry , stereochemistry , organic chemistry , computational chemistry , microbiology and biotechnology , mechanical engineering , biology , engineering
To gain insight into the chemical nature of drug‐induced photoallergy, model studies have been carried out on the photochemical modification of proteins by tiaprofenic acid. Irradiation of decarboxylated tiaprofenic acid (DTPA) in the presence of p ‐cresol leads to C–C‐ and C–O‐connected p ‐cresol “dimers”, together with DTPA hydrodimers. The p ‐cresol–DTPA cross‐coupling product was not detected in this reaction. However, a product of this type is formed using a more hindered phenol, such as 2,6‐di‐ tert ‐butylphenol. Similar results are obtained when tiaprofenic acid (TPA) or its methyl ester are used as photosensitizers. The observed formation of “dimers” can be related to protein photo‐crosslinking, through the coupling of two tyrosine units. On the other hand, phenol–(D)TPA cross‐coupling may be relevant to the understanding of drug–protein photobinding.