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X-ray crystallographic study of several 2′-deoxy-β-d-ribonucleosides with 1-deazapurine-derived aglycones


Müller, J; Polonius, F A; Freisinger, E; Bardají, E G (2008). X-ray crystallographic study of several 2′-deoxy-β-d-ribonucleosides with 1-deazapurine-derived aglycones. Carbohydrate Research, 343(2):397-403.

Abstract

The 2′-deoxy-β-d-ribonucleosides of 1,3-deazapurine (benzimidazole (1)), 1-deazapurine (both 1H-imidazo[4,5-b]pyridine (2) and 3H-imidazo[4,5-b]pyridine (3)), and 6-benzoylamino-1-deazapurine (7-benzoylamino-3H-imidazo[4,5-b]pyridine (4)) have been prepared and structurally characterized by X-ray crystallography. Especially compounds 1–3 can serve as artificial nucleosides that may substitute 2′-deoxy adenosine because they lack the exocyclic amino group and one or two of the endocyclic nitrogen atoms and hence have a much smaller potential to engage in hydrogen bonds. In the latter respect, they are candidates for nucleosides in metal-ion mediated base pairs. The unit cell of compound 3 contains two crystallographically independent molecules. Compound 4 was crystallized from methanol and water, respectively, giving rise to two different solvates. Despite the closely related aglycones, the sugar conformations in 1–4 are found to be highly variable (1: 2T1; 2: 3T2; 3: 3E and E4; 4: 2E and 2T3). The structures reported here confirm that there is no simple correlation between the sugar conformation and the character of the nucleoside, and they will hopefully contribute to a better understanding of the complex interplay of different effects that are in control of the conformational equilibrium.

Abstract

The 2′-deoxy-β-d-ribonucleosides of 1,3-deazapurine (benzimidazole (1)), 1-deazapurine (both 1H-imidazo[4,5-b]pyridine (2) and 3H-imidazo[4,5-b]pyridine (3)), and 6-benzoylamino-1-deazapurine (7-benzoylamino-3H-imidazo[4,5-b]pyridine (4)) have been prepared and structurally characterized by X-ray crystallography. Especially compounds 1–3 can serve as artificial nucleosides that may substitute 2′-deoxy adenosine because they lack the exocyclic amino group and one or two of the endocyclic nitrogen atoms and hence have a much smaller potential to engage in hydrogen bonds. In the latter respect, they are candidates for nucleosides in metal-ion mediated base pairs. The unit cell of compound 3 contains two crystallographically independent molecules. Compound 4 was crystallized from methanol and water, respectively, giving rise to two different solvates. Despite the closely related aglycones, the sugar conformations in 1–4 are found to be highly variable (1: 2T1; 2: 3T2; 3: 3E and E4; 4: 2E and 2T3). The structures reported here confirm that there is no simple correlation between the sugar conformation and the character of the nucleoside, and they will hopefully contribute to a better understanding of the complex interplay of different effects that are in control of the conformational equilibrium.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:2´-Deoxyribonucleosides, structure; 1-Deazapurine; 1,3-Deazapurine; Benzimidazole; 1-Deazaadenine, protected derivative 2
Language:English
Date:February 2008
Deposited On:27 Feb 2009 09:27
Last Modified:05 Apr 2016 13:01
Publisher:Elsevier
ISSN:0008-6215
Publisher DOI:https://doi.org/10.1016/j.carres.2007.11.007
PubMed ID:18045576

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