Artificial genetic systems: exploiting the "aromaticity" formalism to improve the tautomeric ratio for isoguanosine derivatives.
The tautomerism of 2'-deoxy-7-deaza-isoguanosine (2) was studied and compared to that of 2'-deoxyisoguanosine (1). The fixed (1)N-methyl (8) and O-methyl (4) derivatives were synthesized to represent the pure extremes of each tautomer. The replacement of the imidazole ring in 1 with a pyrrole ring in 2 makes the keto form in the latter more favored by 2 orders of magnitude (K(TAUT) for 2 approximately 10(3), as opposed to K(TAUT) for 1 approximately 10).
Martinot
Theodore A
TA
Department of Chemistry, University of Florida, P.O. Box 117200, Gainesville, Florida 32611-7200, USA.
Benner
Steven A
SA
D005823:Genetics; D006151:Guanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D007256:Information Systems; D007536:Isomerism; D015394:Molecular Structure; D013056:Spectrophotometry, Ultraviolet
D006151:Guanosine