Abstract
The recognition ability of pteridine derivatives for nucleobases opposite an abasic (AP) site in an oligodeoxynucleotide (ODN) duplex is enhanced by using a propylene residue (Spacer-C3) as an AP site. The recognition ability is further enhanced both by attaching methyl groups to a fluorescent ligand and by measuring the fluorescence response at 5°C; 6.2 × 106 M-1 of the binding constant is attained between 2-amino-6,7-dimethyl-4-hydroxypteridine and guanine opposite the AP site in water.
References
R. Sachidanandam, D. Weismann, S. C. Schidt, J. M. Kakol, L. D. Stein, G. Marth, S. Sherry, J. C. Mullikin, B. J. Mortimore, D. L. Willey, S. E. Hunt, C. G. Cole, P. C. Coggill, C. M. Rice, Z. Ning, J. Rogers, D. R. Bentley, P.-Y. Kwok, E. R. Mardis, R. T. Yeh, B. Schultz, L. Cook, R. Davenport, M. Gante, L. Fulton, L. Hillier, R. H. Waterston, J. D. McPherson, B. Gilman, S. Schaffner, W. J. V. Etten, D. Reich, J. Higgins, M. J. Daly, B. Blumenstiel, J. Baldwin, N. S. Thomann, M. C. Zody, L. Linton, E. S. Lander, and D. Altshuler, Nature, 2001, 409, 928.
P. Y. Kwok, Annu. Rev. Genomics Hum. Genet., 2001, 2, 235.
D. G. Wang, J. B. Fan, C. J. Siao, A. Berno, P. Young, R. Sapolsky, G. Ghandour, N. Perkins, E. Winchester, J. Spencer, L. Kruglyak, L. Stein, L. Hsie, T. Topaloglou, E. Hubbell, E. Robinson, M. Mittmann, M. S. Morris, N. Shen, D. Kiburn, J. Rioux, C. Nusbaum, S. Rozen, T. J. Hudson, R. Lipshutz, M. Chee, and E. S. Lander, Science, 1998, 280, 1077.
X.-N. Chen, B. Zehnbauer, A. Gnirke, and P.-Y. Kwok, Proc. Natl. Acad. Sci. USA, 1997, 94, 10756.
S. Tyagi, D. P. Bratu, and F. R. Kramer, Nat. Biotechnol., 1998, 16, 49.
V. Lyamichev, M. A. Brow, and J. E. Dahlberg, Science, 1993, 260, 778.
P. Ross, L. Hall, I. Smirnov, and L. Haff, Nat. Biotechnol., 1998, 16, 1347.
K. Nakatani, S. Sando, and I. Saito, Nat. Biotechnol., 2001, 19, 51.
K. Yoshimoto, S. Nishizawa, M. Minagawa, and N. Teramae, J. Am. Chem. Soc., 2003, 125, 8982.
K. Yoshimoto, C.-Y. Xu, S. Nishizawa, T. Haga, H. Satake, and N. Teramae, Chem. Commun., 2003, 2960.
S. Nishizawa, K. Yoshimoto, T. Seino, C.-Y. Xu, M. Minagawa, H. Satake, A. Tong, and N. Teramae, Talanta, 2004, 63, 175.
S. Nishizawa, K. Yoshimoto, T. Seino, C.-Y. Xu, and N. Teramae, Bunseki Kagaku, 2004, 53, 383.
S. Nishizawa, N. B. Sankaran, T. Seino, Y.-Y. Cui, Qing Dai, C.-Y. Xu, K. Yoshimoto, and N. Teramae, Anal. Chim. Acta, 2006, 556, 133.
N. B. Sankaran, S. Nishizawa, T. Seino, K. Yoshimoto, and N. Teramae, Angew. Chem., Int. Ed., in press, DOI: 1002.1002/anie.200502979.
B. Demole and L. Harrison, Annu. Rev. Biochem., 1994, 63, 915.
L. C. Sowers, B. R. Shaw, and W. D. Sedwick, Biochem. Biophys. Res. Commun., 1987, 148, 790.
S. Wang and E. T. Kool, Biochemistry, 1995, 34, 4125.
T. Itahara, Bull. Chem. Soc. Jpn., 2000, 73, 1621.
J. D. Puglisi and I. Tinoco, Jr., Method Enzymol., 1989, 180, 304.
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Dai, Q., Xu, CY., Sato, Y. et al. Enhancement of the Binding Ability of a Ligand for Nucleobase Recognition by Introducing a Methyl Group. ANAL. SCI. 22, 201–203 (2006). https://doi.org/10.2116/analsci.22.201
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DOI: https://doi.org/10.2116/analsci.22.201