Structural and enzymic properties of adenine 1-oxide nucleotides

Par Conseil national de recherches du Canada

DOI	Trouver le DOI : https://doi.org/10.1021/bi00697a009
Auteur	Rechercher : Mantsch, H. H.; Rechercher : Goia, I.; Rechercher : Kezdi, M.; Rechercher : Bârzu, O.; Rechercher : Dânsoreanu, M.; Rechercher : Jebeleanu, G.; Rechercher : Ty, N. G.
Format	Texte, Article
Résumé	We describe the preparation of adenine 1-oxide nucleotides by oxidation of the natural compounds with monopermaleic acid in aqueous solutions at neutral pH, with an overall yield after chromatographic purification between 75 and 80%. If irradiated, the adenine 1-oxide nucleotides undergo a photochemical rearrangement reaction, the main photoproducts in aqueous solution at alkaline pH being the corresponding isoguanine nucleotides. The modified ring vibration pattern of the 1-oxide analogues as well as the I3C chemical shift indicate a loss of aromaticity as compared to the natural compounds. Coupling constant measurements show that the dihedral angle between the 3’POC and OCT3C planes is around 180°, i.e., trans, as in the natural adenine nucleotides. The modified adenine nucleotides were tested as potential substrates and/or inhibitors of mitochondrial processes, as substrates of various phosphotransferases from mitochondria or cytosol, and as allosteric effectors in the reactions catalyzed by glutamate dehydrogenase and phosphofructokinase. Although the adenine 1 -oxide nucleotides are not recognized by the translocase system of the inner mitochondrial membrane, they are good substrates for mitochondrial phosphotransferases located in the intermembrane space. Similarly, they participate in the phosphoryl group transfer reactions catalyzed by pyruvate kinase, phosphofructokinase, and hexokinase. As allosteric effectors, the modified nucleotides are less active than the natural compounds, probably because of a lower binding capacity to the allosteric sites of the regulatory enzymes.
Date de publication	1975-12
Dans	Biochemistry 14, nº 26 : 5593–5601.
Langue	anglais
Publications évaluées par des pairs	Oui
Publication du CNRC	Cette publication n’est pas du CNRC Ce sont des publications qui ont été rédigées par un auteur du CNRC, mais avant que celui-ci soit employé du CNRC.
Numéro NPARC	23001739
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Identificateur de l’enregistrement	a26ede5f-cfcb-4efa-825d-5729fce9842d
Enregistrement créé	2017-03-24
Enregistrement modifié	2020-03-13

Date de modification :: 2024-04-18