Theoretical calculations, synthesis and base pairing properties of oligonucleotides containing 8-amino-2'-deoxyadenosine | Zendy

R. García | Zendy; Elisenda Ferrer | Zendy; María J. Macías | Zendy; Ramón Eritja | Zendy; Modesto Orozco | Zendy

Open Access

Theoretical calculations, synthesis and base pairing properties of oligonucleotides containing 8-amino-2'-deoxyadenosine

Author(s) -

R. García,

Elisenda Ferrer,

María J. Macías,

Ramón Eritja,

Modesto Orozco

Publication year - 1999

Publication title -

nucleic acids research

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 9.008

H-Index - 537

eISSN - 1362-4954

pISSN - 0305-1048

DOI - 10.1093/nar/27.9.1991

Subject(s) - biology , deoxyadenosine , oligonucleotide , pairing , base pair , nucleic acid , base (topology) , genetics , dna , oligonucleotide synthesis , biochemistry , computational biology , physics , superconductivity , quantum mechanics , mathematical analysis , mathematics

Theoretical calculations on double and triple helices containing 8-amino-2'-deoxyadenosine were made to analyze the possible differences in base pairing properties between 8-aminoadenine and adenine. These calculations indicate a strong preferential stabilization of the triplex over the duplex when adenine is replaced by 8-aminoadenine. In addition, a protected phosphoramidite derivative of 8-amino-2'-deoxyadenosine was prepared for the introduction of 8-aminoadenine into synthetic oligonucleotides using the phosphite-triester approach. DNA triple helical structures are normally observed at acidic pH. However, when oligonucleotides carrying 8-aminoadenine are used, very stable triple helical structures can be observed even at neutral pH. Biological applications of triple helices could benefit from the use of 8-aminoadenine derivatives.

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