Synthesis, characterisation and theoretical calculations of 2,6-diaminopurine etheno derivatives

P Virta; A Koch; MU Roslund; Peter Mattjus; E Kleinpeter; Leif Kronberg; Rainer Sjöholm; KD Klika

doi:10.1039/B505508C

Synthesis, characterisation and theoretical calculations of 2,6-diaminopurine etheno derivatives

P Virta, A Koch, MU Roslund, Peter Mattjus, E Kleinpeter, Leif Kronberg, Rainer Sjöholm, KD Klika

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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.

Original language	Undefined/Unknown
Pages (from-to)	2924–2929
Number of pages	6
Journal	Organic and Biomolecular Chemistry
Volume	3
Issue number	16
DOIs	https://doi.org/10.1039/B505508C
Publication status	Published - 2005
MoE publication type	A1 Journal article-refereed

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10.1039/B505508C

Cite this

@article{f8729729da6c40538c77920b9629bcfc,

title = "Synthesis, characterisation and theoretical calculations of 2,6-diaminopurine etheno derivatives",

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.",

author = "P Virta and A Koch and MU Roslund and Peter Mattjus and E Kleinpeter and Leif Kronberg and Rainer Sj{\"o}holm and KD Klika",

year = "2005",

doi = "10.1039/B505508C",

language = "Odefinierat/ok{\"a}nt",

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pages = "2924–2929",

journal = "Organic and Biomolecular Chemistry",

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publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Synthesis, characterisation and theoretical calculations of 2,6-diaminopurine etheno derivatives

AU - Virta, P

AU - Koch, A

AU - Roslund, MU

AU - Mattjus, Peter

AU - Kleinpeter, E

AU - Kronberg, Leif

AU - Sjöholm, Rainer

AU - Klika, KD

PY - 2005

Y1 - 2005

N2 - 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.

AB - 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.

U2 - 10.1039/B505508C

DO - 10.1039/B505508C

M3 - Artikel

SN - 1477-0520

VL - 3

SP - 2924

EP - 2929

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 16

ER -