TY - JOUR
T1 - High-temperature solvolysis of 2′-deoxyribonucleosides in aqueous amine solutions
AU - González-Olvera, Julio C.
AU - González-Jasso, Eva
AU - Rojas-Molina, Alejandra
AU - Pless, Reynaldo C.
N1 - Publisher Copyright:
© 2019, © 2019 Taylor & Francis Group, LLC.
PY - 2019/9/2
Y1 - 2019/9/2
N2 - 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.
AB - 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.
KW - Aminolysis sequencing
KW - DNA base
KW - deoxyribonucleosides
KW - oligonucleotides
KW - pyrrolidine
UR - http://www.scopus.com/inward/record.url?scp=85063936836&partnerID=8YFLogxK
U2 - 10.1080/15257770.2019.1597111
DO - 10.1080/15257770.2019.1597111
M3 - Artículo
C2 - 30942138
AN - SCOPUS:85063936836
SN - 1525-7770
VL - 38
SP - 642
EP - 655
JO - Nucleosides, Nucleotides and Nucleic Acids
JF - Nucleosides, Nucleotides and Nucleic Acids
IS - 9
ER -