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 produ...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2005-08, Vol.3 (16), p.2924-2929
Main Authors: Virta, Piritta, Koch, Andreas, Roslund, Mattias U, Mattjus, Peter, Kleinpeter, Erich, Kronberg, Leif, Sjöholm, Rainer, Klika, Karel D
Format: Article
Language:English
Subjects:
2-Aminopurine - analogs & derivatives
2-Aminopurine - chemical synthesis
2-Aminopurine - chemistry
DNA Adducts - chemical synthesis
DNA Adducts - chemistry
Fluorescence
Magnetic Resonance Spectroscopy
Models, Molecular
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/b505508c