3′-Modified oligodeoxyribonucleotides for the study of 2-deoxyribose damage in DNA

Buthina Al-Oudat; Alex Salyer; Kevin Trabbic; Amanda Bryant-Friedrich

doi:10.1016/j.bmcl.2012.11.050

3′-Modified oligodeoxyribonucleotides for the study of 2-deoxyribose damage in DNA

Buthina Al-Oudat, Alex Salyer, Kevin Trabbic, Amanda Bryant-Friedrich

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

Well-defined substrates for the study of oxidative processes are important for the elucidation of the role of DNA damage in the etiology of diseases such as cancer. We have synthesized 3′-modified oligodeoxyribonucleotides (ODNs) using 5′ → 3′ 'reverse' DNA synthesis for the study of 2-deoxyribose oxidative damage to DNA. The modified monomers designed for these studies all share a common feature, they lack the naturally occurring 3′-hydroxyl group found in 2-deoxyribonucleosides. Modified H-phosphonates containing 3′-phenyl selenides as well as saturated and unsaturated sugars were obtained and incorporated in ODNs. These ODNs were used to investigate the fate of C3′-dideoxyribonucleotide radicals in DNA.

Original language	English (US)
Pages (from-to)	854-859
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	23
Issue number	3
DOIs	https://doi.org/10.1016/j.bmcl.2012.11.050
State	Published - Feb 1 2013
Externally published	Yes

Bibliographical note

Funding Information:
We are grateful for support of this research (CHE-512973) by the National Science Foundation who also provided funding for instrumentation used for MALDI-ToF MS analysis (DBI-923184).

Keywords

DNA damage
H-phosphonate
Oligonucleotides
Radicals
Sugar damage

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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title = "3′-Modified oligodeoxyribonucleotides for the study of 2-deoxyribose damage in DNA",

abstract = "Well-defined substrates for the study of oxidative processes are important for the elucidation of the role of DNA damage in the etiology of diseases such as cancer. We have synthesized 3′-modified oligodeoxyribonucleotides (ODNs) using 5′ → 3′ 'reverse' DNA synthesis for the study of 2-deoxyribose oxidative damage to DNA. The modified monomers designed for these studies all share a common feature, they lack the naturally occurring 3′-hydroxyl group found in 2-deoxyribonucleosides. Modified H-phosphonates containing 3′-phenyl selenides as well as saturated and unsaturated sugars were obtained and incorporated in ODNs. These ODNs were used to investigate the fate of C3′-dideoxyribonucleotide radicals in DNA.",

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AU - Salyer, Alex

AU - Trabbic, Kevin

AU - Bryant-Friedrich, Amanda

N1 - Funding Information: We are grateful for support of this research (CHE-512973) by the National Science Foundation who also provided funding for instrumentation used for MALDI-ToF MS analysis (DBI-923184).

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N2 - Well-defined substrates for the study of oxidative processes are important for the elucidation of the role of DNA damage in the etiology of diseases such as cancer. We have synthesized 3′-modified oligodeoxyribonucleotides (ODNs) using 5′ → 3′ 'reverse' DNA synthesis for the study of 2-deoxyribose oxidative damage to DNA. The modified monomers designed for these studies all share a common feature, they lack the naturally occurring 3′-hydroxyl group found in 2-deoxyribonucleosides. Modified H-phosphonates containing 3′-phenyl selenides as well as saturated and unsaturated sugars were obtained and incorporated in ODNs. These ODNs were used to investigate the fate of C3′-dideoxyribonucleotide radicals in DNA.

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KW - H-phosphonate

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KW - Radicals

KW - Sugar damage

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3′-Modified oligodeoxyribonucleotides for the study of 2-deoxyribose damage in DNA

Abstract

Bibliographical note

Keywords

UN SDGs

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