Medizinische Universität Graz Austria/Österreich - Forschungsportal - Medical University of Graz
Gewählte Publikation:
Reibnegger, G; Pauschenwein, J; Werner, ER.
Electronic structure of tetrahydropteridine derivatives
PTERIDINES 1999 10: 91-94.
Doi: 10.1515/pteridines.1999.10.3.91
Web of Science
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- Führende Autor*innen der Med Uni Graz
- Reibnegger Gilbert
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- Abstract:
- Recently the 4-amino analogue of tetrahydrobiopterin was found to be a strong inhibitor of nitric oxide synthase while being bound to the enzyme in a manner similar to the natural cofactor tetrahydrobiopterin. We were interested in the electronic properties of these and similar compounds and studied therefore the following model tetrahydropteridine structures: tetrahydrolumazine, tetrahydropterin, 4-amino-analogue of tetrahydropterin and N5-methyl-tetrahydropterin. Ab initio quantum chemical computations used the Hartree-Fock method with basis set 6-31GX** after geometry optimization with basis set 3-21G*. Results reveal dramatic differences in distribution of electronic charge and all the molecular properties derived thereof, between a) the lumazine system, b) the normal pterin system, and c) the 4-amino analogue. In contrast, differences of electronic properties between tetrahydropterin and its N5-methyl-derivative are negligible. Our results are compatible with recent speculations that the striking differences between the effects of the tetrahydropterin structure and its 4-amino analogue on enzymatic activity may be due to electronic interaction between the pyrimidine moiety of the pterin ring system and the heme group.
- Find related publications in this database (Keywords)
- Ab initio
- quantum chemistry
- visualization
- pteridines
- nitric oxide synthase