We describe the reaction of formamide with 2′-deoxyadenosine and 2′-deoxyguanosine to give imidazole ringopeningbynucleophilicadditionontheelectrophilicC(8)-positionofthepurinering. Thisinformationallows improvement of the one-lane chemical DNA sequencing procedure based on the base-selective reaction of formamide with DNA. The reactivity with formamide of several 7-deazapurine analogues (7-deaza-2′-deoxyinosine, 7-deaza- 2′-deoxyguanosine, and 7-deaza-2′-deoxyadenosine) incorporated into polynucleotides is also described. The wide spectrum of different sensitivities to formamide displayed by these purine analogues provides the single-lane DNA chemical sequencing procedures with the possibility of specificity.

Mechanism of degradation of purines nucleosides by formamide. Implications for chemical DNA sequencing procedures

CRESTINI C;
1996-01-01

Abstract

We describe the reaction of formamide with 2′-deoxyadenosine and 2′-deoxyguanosine to give imidazole ringopeningbynucleophilicadditionontheelectrophilicC(8)-positionofthepurinering. Thisinformationallows improvement of the one-lane chemical DNA sequencing procedure based on the base-selective reaction of formamide with DNA. The reactivity with formamide of several 7-deazapurine analogues (7-deaza-2′-deoxyinosine, 7-deaza- 2′-deoxyguanosine, and 7-deaza-2′-deoxyadenosine) incorporated into polynucleotides is also described. The wide spectrum of different sensitivities to formamide displayed by these purine analogues provides the single-lane DNA chemical sequencing procedures with the possibility of specificity.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10278/3710150
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