Synthesis, characterisation and theoretical calculations of 2,6-diaminopurine etheno derivatives.
Four derivatives of 2,6-diaminopurine (1) were synthesised and characterised. When 1 was reacted with chloroacetaldehyde, 5-aminoimidazo[2,1-i]purine (2), 9-aminoimidazo[2,1-b]purine (3), 9-aminoimidazo[1,2-a]purine (4) and diimidazo[2,1-b:2',1'-i]purine (5) were formed. The purified products (3-5) were fully characterised by MS, complete NMR assignments as well as fluorescence and UV spectroscopy. The purified, isolated yields of these products (3-5) varied from 2.5 to 30%. The relative stability of different tautomers was investigated by theoretical calculations. Fluorescence characteristics are also discussed and compared to the starting material 1 and a reference molecule 2-aminopurine.
Virta
Piritta
P
Department of Organic Chemistry, Abo Akademi University, FI-20500 Turku/Abo, Finland. piritta.virta@abo.fi
Koch
Andreas
A
Roslund
Mattias U
MU
Mattjus
Peter
P
Kleinpeter
Erich
E
Kronberg
Leif
L
Sjöholm
Rainer
R
Klika
Karel D
KD
D015075:2-Aminopurine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D018736:DNA Adducts / Q000138:chemical synthesis* / Q000737:chemistry; D005453:Fluorescence; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular
D018736:DNA Adducts; D015075:2-Aminopurine; C007300:2,6-diaminopurine