Synthesis, characterisation and theoretical calculations of 2,6-diaminopurine etheno derivatives
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Published on: July 6, 2016
Piritta Virta1, Andreas Koch, Mattias U Roslund
1Department of Organic Chemistry, Abo Akademi University, FI-20500 Turku/Abo, Finland. piritta.virta@abo.fi
Abstract:
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.
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