Synthesis, characterisation and theoretical calculations of 2,6-diaminopurine etheno derivatives |
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Authors: | Virta Piritta Koch Andreas Roslund Mattias U Mattjus Peter Kleinpeter Erich Kronberg Leif Sjöholm Rainer Klika Karel D |
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Institution: | Department of Organic Chemistry, Abo Akademi University, FI-20500 Turku/Abo, Finland. piritta.virta@abo.fi |
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Abstract: | Four derivatives of 2,6-diaminopurine (1) were synthesised and characterised. When 1 was reacted with chloroacetaldehyde, 5-aminoimidazo2,1-i]purine (2), 9-aminoimidazo2,1-b]purine (3), 9-aminoimidazo1,2-a]purine (4) and diimidazo2,1-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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