Direct synthesis and characterization of site-specific deoxyguanosyl and deoxyadenosyl adducts derived from the binding of PAH diol epoxides to oligonucleotides

S. Amin; A. Laryea; M. Cosman; T. Liu; R. Xu; S. Dwarakanath; B. Mao; S. Smirnov; R. G. Harvey; S. S. Hecht; N. E. Geacintov

doi:10.1080/10406639608034690

Direct synthesis and characterization of site-specific deoxyguanosyl and deoxyadenosyl adducts derived from the binding of PAH diol epoxides to oligonucleotides

S. Amin, A. Laryea, M. Cosman, T. Liu, R. Xu, S. Dwarakanath, B. Mao, S. Smirnov, R. G. Harvey, S. S. Hecht, N. E. Geacintov

Chemistry

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

Abstract

The direct synthesis method is a relatively simple approach for generating modified oligonucleotides of defined base sequence with site-specifically placed polycyclic aromatic hydrocarbon diol epoxide-modified deoxyguanosyl and deoxyadenosyl residues. Up to 5-10 mg quantities of several different modified oligonucleotides have been synthesized for detailed NMR structural studies. Smaller amounts of modified oligonucleotides containing a single modified guanosyl residue in oligonucleotides 10-11 bases long containing up to three other unmodified guanine residues can be readily generated in smaller quantities for site-directed mutagenesis and other studies.

Original language	English (US)
Pages (from-to)	137-144
Number of pages	8
Journal	Polycyclic Aromatic Compounds
Volume	10
Issue number	1-4
DOIs	https://doi.org/10.1080/10406639608034690
State	Published - 1996

Keywords

Benzo[a]pyrene
Mutagenesis
NMR structures
PAH diol epoxides
Site-specific PAH-DNA adducts

ASJC Scopus subject areas

Organic Chemistry
Polymers and Plastics
Materials Chemistry

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10.1080/10406639608034690

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Amin, S., Laryea, A., Cosman, M., Liu, T., Xu, R., Dwarakanath, S., Mao, B., Smirnov, S., Harvey, R. G., Hecht, S. S., & Geacintov, N. E. (1996). Direct synthesis and characterization of site-specific deoxyguanosyl and deoxyadenosyl adducts derived from the binding of PAH diol epoxides to oligonucleotides. Polycyclic Aromatic Compounds, 10(1-4), 137-144. https://doi.org/10.1080/10406639608034690

Amin, S, Laryea, A, Cosman, M, Liu, T, Xu, R, Dwarakanath, S, Mao, B, Smirnov, S, Harvey, RG, Hecht, SS & Geacintov, NE 1996, 'Direct synthesis and characterization of site-specific deoxyguanosyl and deoxyadenosyl adducts derived from the binding of PAH diol epoxides to oligonucleotides', Polycyclic Aromatic Compounds, vol. 10, no. 1-4, pp. 137-144. https://doi.org/10.1080/10406639608034690

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title = "Direct synthesis and characterization of site-specific deoxyguanosyl and deoxyadenosyl adducts derived from the binding of PAH diol epoxides to oligonucleotides",

abstract = "The direct synthesis method is a relatively simple approach for generating modified oligonucleotides of defined base sequence with site-specifically placed polycyclic aromatic hydrocarbon diol epoxide-modified deoxyguanosyl and deoxyadenosyl residues. Up to 5-10 mg quantities of several different modified oligonucleotides have been synthesized for detailed NMR structural studies. Smaller amounts of modified oligonucleotides containing a single modified guanosyl residue in oligonucleotides 10-11 bases long containing up to three other unmodified guanine residues can be readily generated in smaller quantities for site-directed mutagenesis and other studies.",

keywords = "Benzo[a]pyrene, Mutagenesis, NMR structures, PAH diol epoxides, Site-specific PAH-DNA adducts",

author = "S. Amin and A. Laryea and M. Cosman and T. Liu and R. Xu and S. Dwarakanath and B. Mao and S. Smirnov and Harvey, {R. G.} and Hecht, {S. S.} and Geacintov, {N. E.}",

note = "Funding Information: This work was supported by the Department of Health and Human Services, National Institutes of Health, National Cancer Institute, Grant CA 57226.",

year = "1996",

doi = "10.1080/10406639608034690",

language = "English (US)",

volume = "10",

pages = "137--144",

journal = "Polycyclic Aromatic Compounds",

issn = "1040-6638",

publisher = "Taylor and Francis Ltd.",

number = "1-4",

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T1 - Direct synthesis and characterization of site-specific deoxyguanosyl and deoxyadenosyl adducts derived from the binding of PAH diol epoxides to oligonucleotides

AU - Amin, S.

AU - Laryea, A.

AU - Cosman, M.

AU - Liu, T.

AU - Xu, R.

AU - Dwarakanath, S.

AU - Mao, B.

AU - Smirnov, S.

AU - Harvey, R. G.

AU - Hecht, S. S.

AU - Geacintov, N. E.

N1 - Funding Information: This work was supported by the Department of Health and Human Services, National Institutes of Health, National Cancer Institute, Grant CA 57226.

PY - 1996

Y1 - 1996

N2 - The direct synthesis method is a relatively simple approach for generating modified oligonucleotides of defined base sequence with site-specifically placed polycyclic aromatic hydrocarbon diol epoxide-modified deoxyguanosyl and deoxyadenosyl residues. Up to 5-10 mg quantities of several different modified oligonucleotides have been synthesized for detailed NMR structural studies. Smaller amounts of modified oligonucleotides containing a single modified guanosyl residue in oligonucleotides 10-11 bases long containing up to three other unmodified guanine residues can be readily generated in smaller quantities for site-directed mutagenesis and other studies.

AB - The direct synthesis method is a relatively simple approach for generating modified oligonucleotides of defined base sequence with site-specifically placed polycyclic aromatic hydrocarbon diol epoxide-modified deoxyguanosyl and deoxyadenosyl residues. Up to 5-10 mg quantities of several different modified oligonucleotides have been synthesized for detailed NMR structural studies. Smaller amounts of modified oligonucleotides containing a single modified guanosyl residue in oligonucleotides 10-11 bases long containing up to three other unmodified guanine residues can be readily generated in smaller quantities for site-directed mutagenesis and other studies.

KW - Benzo[a]pyrene

KW - Mutagenesis

KW - NMR structures

KW - PAH diol epoxides

KW - Site-specific PAH-DNA adducts

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DO - 10.1080/10406639608034690

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AN - SCOPUS:0030359372

SN - 1040-6638

VL - 10

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EP - 144

JO - Polycyclic Aromatic Compounds

JF - Polycyclic Aromatic Compounds

IS - 1-4

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Direct synthesis and characterization of site-specific deoxyguanosyl and deoxyadenosyl adducts derived from the binding of PAH diol epoxides to oligonucleotides

Abstract

Keywords

ASJC Scopus subject areas

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