Convenient and efficient syntheses of oligodeoxyribonucleotides containing O 6-(carboxymethyl)guanine and O 6-(4-Oxo-4-(3-pyridyl) butyl)guanine

Christopher L. Millington; Amanda J. Watson; Andrew S. Marriott; Geoffrey P. Margison; Andrew C. Povey; David M. Williams

doi:10.1080/15257770.2012.656784

Convenient and efficient syntheses of oligodeoxyribonucleotides containing O 6-(carboxymethyl)guanine and O 6-(4-Oxo-4-(3-pyridyl) butyl)guanine

Christopher L. Millington, Amanda J. Watson, Andrew S. Marriott, Geoffrey P. Margison, Andrew C. Povey, David M. Williams

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

Abstract

O 6-(carboxymethyl)guanine (O 6-CMG) and O 6-(4-oxo-4-(3-pyridyl)butyl)guanine (O 6-pobG) are toxic lesions formed in DNA following exposure to alkylating agents. O 6-CMG results from exposure to nitrosated glycine or nitrosated bile acid conjugates and may be associated with diets rich in red meat. O 6-pobG lesions are derived from alkylating agents found in tobacco smoke. Efficient syntheses of oligodeoxyribonucleotides (ODNs) containing O 6-CMG and O 6-pobG are described that involve nucleophilic displacement by the appropriate alcohol on a common synthetic ODN containing the reactive base 2-amino-6-methylsulfonylpurine. ODNs containing O 6-pobG and O 6-CMG were found to be good substrates for the S. pombe alkyltransferase-like protein Atl1. [Supplemental materials are available for this article. Go to the publisher's online edition of Nucleosides, Nucleotides & Nucleic Acids to view the free supplemental file. Copyright © Cejera, LLC.

Original language	English
Pages (from-to)	328-333
Number of pages	5
Journal	Nucleosides, Nucleotides and Nucleic Acids
Volume	31
Issue number	4
DOIs	https://doi.org/10.1080/15257770.2012.656784
Publication status	Published - 1 Apr 2012

Keywords

alkyltransferase-like protein
DNA synthesis
O 6-(4-oxo-4-(3-pyridyl) butyl)guanine
O 6-(Carboxymethyl)guanine

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10.1080/15257770.2012.656784

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@article{2254bcba9904488cb710cd90675c242a,

title = "Convenient and efficient syntheses of oligodeoxyribonucleotides containing O 6-(carboxymethyl)guanine and O 6-(4-Oxo-4-(3-pyridyl) butyl)guanine",

abstract = "O 6-(carboxymethyl)guanine (O 6-CMG) and O 6-(4-oxo-4-(3-pyridyl)butyl)guanine (O 6-pobG) are toxic lesions formed in DNA following exposure to alkylating agents. O 6-CMG results from exposure to nitrosated glycine or nitrosated bile acid conjugates and may be associated with diets rich in red meat. O 6-pobG lesions are derived from alkylating agents found in tobacco smoke. Efficient syntheses of oligodeoxyribonucleotides (ODNs) containing O 6-CMG and O 6-pobG are described that involve nucleophilic displacement by the appropriate alcohol on a common synthetic ODN containing the reactive base 2-amino-6-methylsulfonylpurine. ODNs containing O 6-pobG and O 6-CMG were found to be good substrates for the S. pombe alkyltransferase-like protein Atl1. [Supplemental materials are available for this article. Go to the publisher's online edition of Nucleosides, Nucleotides & Nucleic Acids to view the free supplemental file. Copyright {\textcopyright} Cejera, LLC.",

keywords = "alkyltransferase-like protein, DNA synthesis, O 6-(4-oxo-4-(3-pyridyl) butyl)guanine, O 6-(Carboxymethyl)guanine",

author = "Millington, {Christopher L.} and Watson, {Amanda J.} and Marriott, {Andrew S.} and Margison, {Geoffrey P.} and Povey, {Andrew C.} and Williams, {David M.}",

year = "2012",

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doi = "10.1080/15257770.2012.656784",

language = "English",

volume = "31",

pages = "328--333",

journal = "Nucleosides, Nucleotides and Nucleic Acids",

issn = "1532-2335",

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}

Convenient and efficient syntheses of oligodeoxyribonucleotides containing O 6-(carboxymethyl)guanine and O 6-(4-Oxo-4-(3-pyridyl) butyl)guanine. / Millington, Christopher L.; Watson, Amanda J.; Marriott, Andrew S. et al.
In: Nucleosides, Nucleotides and Nucleic Acids, Vol. 31, No. 4, 01.04.2012, p. 328-333.

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

TY - JOUR

T1 - Convenient and efficient syntheses of oligodeoxyribonucleotides containing O 6-(carboxymethyl)guanine and O 6-(4-Oxo-4-(3-pyridyl) butyl)guanine

AU - Millington, Christopher L.

AU - Watson, Amanda J.

AU - Marriott, Andrew S.

AU - Margison, Geoffrey P.

AU - Povey, Andrew C.

AU - Williams, David M.

PY - 2012/4/1

Y1 - 2012/4/1

N2 - O 6-(carboxymethyl)guanine (O 6-CMG) and O 6-(4-oxo-4-(3-pyridyl)butyl)guanine (O 6-pobG) are toxic lesions formed in DNA following exposure to alkylating agents. O 6-CMG results from exposure to nitrosated glycine or nitrosated bile acid conjugates and may be associated with diets rich in red meat. O 6-pobG lesions are derived from alkylating agents found in tobacco smoke. Efficient syntheses of oligodeoxyribonucleotides (ODNs) containing O 6-CMG and O 6-pobG are described that involve nucleophilic displacement by the appropriate alcohol on a common synthetic ODN containing the reactive base 2-amino-6-methylsulfonylpurine. ODNs containing O 6-pobG and O 6-CMG were found to be good substrates for the S. pombe alkyltransferase-like protein Atl1. [Supplemental materials are available for this article. Go to the publisher's online edition of Nucleosides, Nucleotides & Nucleic Acids to view the free supplemental file. Copyright © Cejera, LLC.

AB - O 6-(carboxymethyl)guanine (O 6-CMG) and O 6-(4-oxo-4-(3-pyridyl)butyl)guanine (O 6-pobG) are toxic lesions formed in DNA following exposure to alkylating agents. O 6-CMG results from exposure to nitrosated glycine or nitrosated bile acid conjugates and may be associated with diets rich in red meat. O 6-pobG lesions are derived from alkylating agents found in tobacco smoke. Efficient syntheses of oligodeoxyribonucleotides (ODNs) containing O 6-CMG and O 6-pobG are described that involve nucleophilic displacement by the appropriate alcohol on a common synthetic ODN containing the reactive base 2-amino-6-methylsulfonylpurine. ODNs containing O 6-pobG and O 6-CMG were found to be good substrates for the S. pombe alkyltransferase-like protein Atl1. [Supplemental materials are available for this article. Go to the publisher's online edition of Nucleosides, Nucleotides & Nucleic Acids to view the free supplemental file. Copyright © Cejera, LLC.

KW - alkyltransferase-like protein

KW - DNA synthesis

KW - O 6-(4-oxo-4-(3-pyridyl) butyl)guanine

KW - O 6-(Carboxymethyl)guanine

U2 - 10.1080/15257770.2012.656784

DO - 10.1080/15257770.2012.656784

M3 - Article

SN - 1532-2335

VL - 31

SP - 328

EP - 333

JO - Nucleosides, Nucleotides and Nucleic Acids

JF - Nucleosides, Nucleotides and Nucleic Acids

IS - 4

ER -

Convenient and efficient syntheses of oligodeoxyribonucleotides containing O 6-(carboxymethyl)guanine and O 6-(4-Oxo-4-(3-pyridyl) butyl)guanine

Abstract

Keywords

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