| 학회 | 한국고분자학회 |
| 학술대회 | 2005년 가을 (10/13 ~ 10/14, 제주 ICC) |
| 권호 | 30권 2호 |
| 발표분야 | 유기형광체 |
| 제목 | Fluorescent Oligonucleotides: Synthesis and Application |
| 초록 | The design and synthesis of fluorescent oligonucleotides has been a subject of intensive effort because these oligonucleotide derivatives can be used as tools in molecular biology, diagnostics and structural studies.1 Current interest in our lab is also focused on the development of fluorophore-labeled oligonucleotides that display a strongly enhanced signal upon hybridization with a target DNA. These types of oligonucleotide probes have become very attractive recently because they can be used as single-nucleotide polymorphism (SNP) probes.2 Pyrene-labeled nucleosides synthesized using Sonogashira coupling3,4 at the C-5 position of deoxyuridine with 1-ethynylpyrene can be inserted efficiently into ODNs (Figure 1).5 The relative fluorescence intensities of 1•5, 1, 1•2, 1•3 and 1•4 are 1.9, 1.0, 0.34, 0.46 and 0.69, respectively. Therefore the pyrene-labeled ODN 1 was found to be a sensitive probe that discriminates between perfect and one-base-mismatched base pairing by distinct change in its fluorescence intensity. Figure 1. The synthesized pyrene-labeled oligonucleotides. We have also synthesized, by Sonogashira coupling, a fluorene-containing deoxyuridine derivative that we incorporated into the loop region of a hairpin (Figure 2).6 This hairpin functions as new type of molecular beacon (MB) that requires no fluorescence quencher unit. The fluorescence intensities of single-base-mismatched duplexes are decreased relative to that observed for the hairpin, but are increased upon hybridizing with fully matched sequences. The total discrimination factor is 14.7 for the recognition of a single (A/C) base mismatch. Figure 2. Fluorene-labeled oligonucleotides synthesized for the MB study. ACKNOWLEDGMENTS We are grateful to KOSEF for financial support through the NRL Program (Laboratory for Modified Nucleic Acid Systems). REFERENCES 1. Wojczewski, C.; Stolze, K.; Engels, J. W., Synlett , 1999, 1667. 2. (a)Nakatani, K., ChemBioChem, 2004, 5, 1623. (b) Brookes, A. J., Gene, 1999, 234, 177. (c) Collins, F. S.; Brooks, L. D.; Chakravarti, A., Genome Res., 1998, 8, 1229. 3. (a) Sonogashira, K. Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998. (b) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett., 1975, 4467. 4. (a) Hwang, G. T.; Seo, Y. J.; Kim, B. H., Tetrahedron Lett., 2005, 46 , 1475. (b) Hwang, G. T.; Kim, B. H., Org. Lett., 2004, 6, 2669. (c) Hwang, G. T.; Son, H. S.; Ku, J. K.; Kim, B. H., J. Am. Chem. Soc., 2003, 125, 11241. (d) Hwang, G. T.; Son, H. S.; Ku, J. K.; Kim, B. H., Org. Lett., 2001, 3, 2469 5. Hwang, G. T.; Seo, Y. J.; Kim, S. J.; Kim, B. H., Tetrahedron Lett., 2004, 45, 3543. 6. Hwang, G. T.; Seo, Y. J.; Kim, B. H., J. Am. Chem. Soc., 2004, 126, 6528. |
| 저자 | 김병현 |
| 소속 | Department of Chemistry |
| 키워드 | |
