Base stacking of simple mRNA cap analogues. Association of 7,9-dimethylguanine, 7-methylguanosine and 7-methylguanosine 5'-monophosphate with indole and purine derivatives in aqueous solution.
Equilibrium constants for the association of different ionic forms of 7,9-dimethylguanine, 7-methylguanosine and 7-methylguanosine 5'-monophosphate with indole, caffeine and various methylated adenines have been determined by distributing the latter compounds between an organic solvent and aqueous solutions of the 7-methylguanine derivatives. The data are compared to those obtained for the association of unsubstituted purine with the same cosolutes. The stacking affinity of both cationic and zwitterionic forms of the 7-methylguanine ring correlates with the ring polarizability rather than the polarizing power of the cosolute. The cationic species stacks usually more efficiently. The chemical nature of the N9-substituent has only a moderate influence on the base-stacking properties.
Darzynkiewicz
E
E
Department of Biophysics, University of Warsaw, Poland.
Lönnberg
H
H
D002110:Caffeine; D006147:Guanine / Q000031:analogs & derivatives*; D006151:Guanosine / Q000031:analogs & derivatives; D007211:Indoles; D009690:Nucleic Acid Conformation; D011687:Purines; D012314:RNA Cap Analogs; D012315:RNA Caps; D012996:Solutions; D013329:Structure-Activity Relationship
D007211:Indoles; D011687:Purines; D012314:RNA Cap Analogs; D012315:RNA Caps; D012996:Solutions; C011925:7-methylguanosine-5'-monophosphate; D006151:Guanosine; C016578:7-methylguanosine; D002110:Caffeine; C061517:7,9-dimethylguanine; D006147:Guanine