N2,3-ETHENOGUANOSINE AND IA-METAMORPHOSINE - N-15 NMR-SPECTROSCOPY AND ELUCIDATION OF PHYSICOCHEMICAL PROPERTIES BY KINETIC AND EQUILIBRIUM MEASUREMENTS



: GLEMAREC C, BESIDSKY Y, CHATTOPADHYAYA J, KUSMIEREK J, LAHTI M, OIVANEN M, LONNBERG H

Publisher: PERGAMON-ELSEVIER SCIENCE LTD

: 1991

Tetrahedron

TETRAHEDRON

: TETRAHEDRON

: 47

: 33

: 6689

: 6704

: 16

: 0040-4020

DOI: https://doi.org/10.1016/S0040-4020(01)82321-8


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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