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Nucleic Acids Research, 1977, Vol. 4, No. 3 697-709
© 1977

Articles

Glycosyl conformational and inductive effects on the acid catalysed hydrolysis of purine nucleosides

Frank Jordan and Haggai Niv

Caris A.OIson Laboratories of Chemistry, Rutgers the State University of New Jersey - Newark NJ 07102, USA

Received January 25, 1977. The log kobs vs. pH profiles were determined In the Intermediate acidity region for the glycosyl hydrolysis of guanosine and its 8-amino, 8-monomethyl-amlno, 8-dimethylamino and 8-bromo derivatives. The decreased rate of the 8-amino and enhanced rate of the 8-bromo compound compared to guanosine support an A type mechanism: base protonation followed by glycosyl bond cleavage. All three 8-amlno guanosines exhibited log kobs - pH profiles clearly showing that both mono and dl-base protonated nucleosides undergo hydrolysis. The 700 fold rate acceleration of 8-N(CH3).-guanoslne compared to 8-NHCH3-guanoslne and the 110 fold rate acceleration Of 8-N(CH3)2-adenosine compared to 8-NHCH3-adenosine could be unequivocally attributed to the fixed syn glycosyl conformation of both 8-dimethylamlno compounds and relief of steric compression upon hydrolysis in these molecules. The lack of anomerization of all substrates during the course of the reaction supports an A rather than a Schiff-base mechanism.


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