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Reactive derivative of adenosine‐5′‐triphosphate formed by irradiation of ATP γ‐ p ‐azidoanilide
Author(s) -
Badashkeyeva A.G.,
Gall T.S.,
Efimova E.V.,
Knorre D.G.,
Lebedev A.V.,
Mysina S.D.
Publication year - 1983
Publication title -
febs letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.593
H-Index - 257
eISSN - 1873-3468
pISSN - 0014-5793
DOI - 10.1016/0014-5793(82)80617-0
Subject(s) - chemistry , morpholine , propylamine , nucleophile , derivative (finance) , quinone , reactive intermediate , diimine , photochemistry , stereochemistry , imidazole , adenosine triphosphate , medicinal chemistry , amine gas treating , organic chemistry , financial economics , economics , catalysis
UV and 1 H NMR spectra changes demonstrate that p ‐azidoanilides of ATP, ITP, pyrophosphate after irradiation at 313 nm, transform to similar reactive intermediates. The latter react readily with morpholine, iso‐propylamine, tert ‐butylamine, imidazole, mercaptoethanol the reactivity being qualitatively correlated with nucleophilicity. By analogy with the transformation of p ‐azidoanilide, it is concluded that the reactive intermediate is the respective derivative of quinone diimine. Photoaffinity labelling of proteins with p ‐azidoanilide derivatives may proceed as the reaction of the nucleophilic centers of proteins with this quinone diimine derivative, rather than as a direct attack by a nitrene biradical.