Extreme (10(9)) acidification of adenine-NH2 in an open platinated nucleobase quartet. A pH switch with potential as a biological acid/base catalyst.
The combination of electronic effects (PtII binding to N7 and N1) and a favourable conformation permitting efficient stabilization of the anion brings about a 10(9) fold increase in the exocyclic amino group acidity of 9-ethyladenine.
Lüth
M S
MS
Fachbereich Chemie, Universität Dortmund, 44221 Dortmund, Germany.
Willermann
M
M
Lippert
B
B
D000143:Acids / Q000737:chemistry; D000225:Adenine / Q000031:analogs & derivatives* / Q000737:chemistry*; D002384:Catalysis; D004247:DNA / Q000737:chemistry / Q000378:metabolism; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D000143:Acids; D004247:DNA; D000225:Adenine