High-temperature solvolysis of 2′-deoxyribonucleosides in aqueous amine solutions

Julio C. González-Olvera, Eva González-Jasso, Alejandra Rojas-Molina, Reynaldo C. Pless

Research output: Contribution to journalArticle

Abstract

Degradation of 2′-deoxyribonucleosides in 0.5 M aqueous pyrrolidine at 110 °C proceeds at different rates, ordered as deoxyuridine > deoxyadenosine > deoxycytidine > deoxyguanosine ≫ deoxythymidine. Deoxyadenosine degradation produces the free base, adenine, while deoxycytidine by deamination produces deoxyuridine, and then uracil. The solvolysis of deoxyadenosine has an activation energy of 23.3 kcal/mol. Ammonolysis is slower than pyrrolidinolysis for deoxyadenosine, but faster for deoxyguanosine. In pyrrolidinolysis of the trinucleotides, d-TGT and d-TAT, the guanine moiety reacts faster than the adenine moiety. These trends are interpreted in terms of the ionization of the guanine moieties under basic conditions, rendering them less susceptible to nucleophilic attack.

Original languageEnglish
Pages (from-to)642-655
Number of pages14
JournalNucleosides, Nucleotides and Nucleic Acids
Volume38
Issue number9
DOIs
StatePublished - 2 Sep 2019

Fingerprint

Deoxyribonucleosides
Amines
Deoxyuridine
Deoxycytidine
Deoxyguanosine
Temperature
Guanine
Adenine
Degradation
Deamination
Uracil
Thymidine
Ionization
Activation energy
2'-deoxyadenosine

Keywords

  • Aminolysis sequencing
  • deoxyribonucleosides
  • DNA base
  • oligonucleotides
  • pyrrolidine

Cite this

González-Olvera, Julio C. ; González-Jasso, Eva ; Rojas-Molina, Alejandra ; Pless, Reynaldo C. / High-temperature solvolysis of 2′-deoxyribonucleosides in aqueous amine solutions. In: Nucleosides, Nucleotides and Nucleic Acids. 2019 ; Vol. 38, No. 9. pp. 642-655.
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High-temperature solvolysis of 2′-deoxyribonucleosides in aqueous amine solutions. / González-Olvera, Julio C.; González-Jasso, Eva; Rojas-Molina, Alejandra; Pless, Reynaldo C.

In: Nucleosides, Nucleotides and Nucleic Acids, Vol. 38, No. 9, 02.09.2019, p. 642-655.

Research output: Contribution to journalArticle

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