Abstract
A dodecadeoxyribonucleotide containing a cis-syn thymine dimer with a phosphorodithioate linkage was synthesized on a solid support using a dinucleotide coupling unit prepared by UV-irradiation of dithymidine monophosphorodithioate followed by S- and 5'-O-protection and 3'-phosphitylation. A photodimer-containing dodecamer without phosphate modification was also synthesized. The dodecamers were hybridized to the complementary sequence, and the duplexes used as substrates for T4 endonuclease V. This enzyme cleaved the phosphate-modified substrate more slowly than the unmodified duplex with the same dissociation constant.
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- Bailly V., Sente B., Verly W. G. Bacteriophage-T4 and Micrococcus luteus UV endonucleases are not endonucleases but beta-elimination and sometimes beta delta-elimination catalysts. Biochem J. 1989 May 1;259(3):751–759. doi: 10.1042/bj2590751. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Blake K. R., Murakami A., Spitz S. A., Glave S. A., Reddy M. P., Ts'o P. O., Miller P. S. Hybridization arrest of globin synthesis in rabbit reticulocyte lysates and cells by oligodeoxyribonucleoside methylphosphonates. Biochemistry. 1985 Oct 22;24(22):6139–6145. doi: 10.1021/bi00343a016. [DOI] [PubMed] [Google Scholar]
- Bower M., Summers M. F., Powell C., Shinozuka K., Regan J. B., Zon G., Wilson W. D. Oligodeoxyribonucleoside methylphosphonates. NMR and UV spectroscopic studies of Rp-Rp and Sp-Sp methylphosphonate (Me) modified duplexes of (d[GGAATTCC])2. Nucleic Acids Res. 1987 Jun 25;15(12):4915–4930. doi: 10.1093/nar/15.12.4915. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Inaoka T., Ishida M., Ohtsuka E. Affinity of single- or double-stranded oligodeoxyribonucleotides containing a thymine photodimer for T4 endonuclease V. J Biol Chem. 1989 Feb 15;264(5):2609–2614. [PubMed] [Google Scholar]
- Kemmink J., Boelens R., Koning T. M., Kaptein R., van der Marel G. A., van Boom J. H. Conformational changes in the oligonucleotide duplex d(GCGTTGCG) x d(CGCAACGC) induced by formation of a cis-syn thymine dimer. A two-dimensional NMR study. Eur J Biochem. 1987 Jan 2;162(1):37–43. doi: 10.1111/j.1432-1033.1987.tb10538.x. [DOI] [PubMed] [Google Scholar]
- Kim J., Linn S. The mechanisms of action of E. coli endonuclease III and T4 UV endonuclease (endonuclease V) at AP sites. Nucleic Acids Res. 1988 Feb 11;16(3):1135–1141. doi: 10.1093/nar/16.3.1135. [DOI] [PMC free article] [PubMed] [Google Scholar]
- LaPlanche L. A., James T. L., Powell C., Wilson W. D., Uznanski B., Stec W. J., Summers M. F., Zon G. Phosphorothioate-modified oligodeoxyribonucleotides. III. NMR and UV spectroscopic studies of the Rp-Rp, Sp-Sp, and Rp-Sp duplexes, [d(GGSAATTCC)]2, derived from diastereomeric O-ethyl phosphorothioates. Nucleic Acids Res. 1986 Nov 25;14(22):9081–9093. doi: 10.1093/nar/14.22.9081. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Marcus-Sekura C. J., Woerner A. M., Shinozuka K., Zon G., Quinnan G. V., Jr Comparative inhibition of chloramphenicol acetyltransferase gene expression by antisense oligonucleotide analogues having alkyl phosphotriester, methylphosphonate and phosphorothioate linkages. Nucleic Acids Res. 1987 Jul 24;15(14):5749–5763. doi: 10.1093/nar/15.14.5749. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Mitchell D. L., Nairn R. S. The biology of the (6-4) photoproduct. Photochem Photobiol. 1989 Jun;49(6):805–819. doi: 10.1111/j.1751-1097.1989.tb05578.x. [DOI] [PubMed] [Google Scholar]
- Nakabeppu Y., Sekiguchi M. Physical association of pyrimidine dimer DNA glycosylase and apurinic/apyrimidinic DNA endonuclease essential for repair of ultraviolet-damaged DNA. Proc Natl Acad Sci U S A. 1981 May;78(5):2742–2746. doi: 10.1073/pnas.78.5.2742. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Seawell P. C., Simon T. J., Ganesan A. K. Binding of T4 endonuclease V to deoxyribonucleic acid irradiated with ultraviolet light. Biochemistry. 1980 Apr 15;19(8):1685–1691. doi: 10.1021/bi00549a026. [DOI] [PubMed] [Google Scholar]
- Smith C. C., Aurelian L., Reddy M. P., Miller P. S., Ts'o P. O. Antiviral effect of an oligo(nucleoside methylphosphonate) complementary to the splice junction of herpes simplex virus type 1 immediate early pre-mRNAs 4 and 5. Proc Natl Acad Sci U S A. 1986 May;83(9):2787–2791. doi: 10.1073/pnas.83.9.2787. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Stein C. A., Subasinghe C., Shinozuka K., Cohen J. S. Physicochemical properties of phosphorothioate oligodeoxynucleotides. Nucleic Acids Res. 1988 Apr 25;16(8):3209–3221. doi: 10.1093/nar/16.8.3209. [DOI] [PMC free article] [PubMed] [Google Scholar]