A1 Refereed original research article in a scientific journal
N2,3-ETHENOGUANOSINE AND IA-METAMORPHOSINE - N-15 NMR-SPECTROSCOPY AND ELUCIDATION OF PHYSICOCHEMICAL PROPERTIES BY KINETIC AND EQUILIBRIUM MEASUREMENTS
Authors: GLEMAREC C, BESIDSKY Y, CHATTOPADHYAYA J, KUSMIEREK J, LAHTI M, OIVANEN M, LONNBERG H
Publisher: PERGAMON-ELSEVIER SCIENCE LTD
Publication year: 1991
Journal:: Tetrahedron
Journal name in source: TETRAHEDRON
Journal acronym: TETRAHEDRON
Volume: 47
Issue: 33
First page : 6689
Last page: 6704
Number of pages: 16
ISSN: 0040-4020
DOI: https://doi.org/10.1016/S0040-4020(01)82321-8
Abstract
Tautomerism, protonation and electronic properties of the base moieties of IA'-metamorphosine (1a), N2,3-ethenoguanosine (2a) and O6-benzyl-N2,3-ethenoguanosine (3a) were investigated by N-15 NMR spectroscopy. pK(a) values of the same compounds were determined spectrophotometrically, and hydrolytic stability of the N-glycosidic bond was studied at various hydronium ion concentrations. The base stacking ability and metal ion complexation of N2,3-ethenoguanosine and its 9-ethyl counterpart (7) were elucidated by phase distribution and potentiometric measurements.
Tautomerism, protonation and electronic properties of the base moieties of IA'-metamorphosine (1a), N2,3-ethenoguanosine (2a) and O6-benzyl-N2,3-ethenoguanosine (3a) were investigated by N-15 NMR spectroscopy. pK(a) values of the same compounds were determined spectrophotometrically, and hydrolytic stability of the N-glycosidic bond was studied at various hydronium ion concentrations. The base stacking ability and metal ion complexation of N2,3-ethenoguanosine and its 9-ethyl counterpart (7) were elucidated by phase distribution and potentiometric measurements.
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