Molecular Design for a Pinpoint RNA Scission. Interposition of Oligoamines between Two DNA Oligomers

Journal of Organic Chemistry

Volumn 62, Issue 4, 1997, Pages 846-852

  Endo, Masayuki ^a   Azuma, Yasushi ^a   Saga, Yoshitaka ^a   Kuzuya, Akinori ^a   Kawai, Gota ^a   Komiyama, Makoto ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000068223     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9611780     Document Type: Article

References (33)

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16. For DNA scission by artificial nucleases, see: (a) Dervan, P. B. Science 1986, 232, 464. (b) Moser, H. E.; Dervan, P. B. Science 1987, 238, 645. (c) Sigman, D. S.; Chen, C. B. Annu. Rev. Biochem. 1990, 59, 207. (d) Nielsen, P. E. Bioconjugate Chem. 1991, 2, 1. (e) Sigman, D. S.; Bruice, T. W.; Mazumder, A.; Sutton, C. L. Acc. Chem. Res. 1993, 26, 98. (f) Thuong, N. T.; Hélène, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 666. (g) Reference 2b.
17. For DNA scission by artificial nucleases, see: (a) Dervan, P. B. Science 1986, 232, 464. (b) Moser, H. E.; Dervan, P. B. Science 1987, 238, 645. (c) Sigman, D. S.; Chen, C. B. Annu. Rev. Biochem. 1990, 59, 207. (d) Nielsen, P. E. Bioconjugate Chem. 1991, 2, 1. (e) Sigman, D. S.; Bruice, T. W.; Mazumder, A.; Sutton, C. L. Acc. Chem. Res. 1993, 26, 98. (f) Thuong, N. T.; Hélène, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 666. (g) Reference 2b.
18. For DNA scission by artificial nucleases, see: (a) Dervan, P. B. Science 1986, 232, 464. (b) Moser, H. E.; Dervan, P. B. Science 1987, 238, 645. (c) Sigman, D. S.; Chen, C. B. Annu. Rev. Biochem. 1990, 59, 207. (d) Nielsen, P. E. Bioconjugate Chem. 1991, 2, 1. (e) Sigman, D. S.; Bruice, T. W.; Mazumder, A.; Sutton, C. L. Acc. Chem. Res. 1993, 26, 98. (f) Thuong, N. T.; Hélène, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 666. (g) Reference 2b.
19. For DNA scission by artificial nucleases, see: (a) Dervan, P. B. Science 1986, 232, 464. (b) Moser, H. E.; Dervan, P. B. Science 1987, 238, 645. (c) Sigman, D. S.; Chen, C. B. Annu. Rev. Biochem. 1990, 59, 207. (d) Nielsen, P. E. Bioconjugate Chem. 1991, 2, 1. (e) Sigman, D. S.; Bruice, T. W.; Mazumder, A.; Sutton, C. L. Acc. Chem. Res. 1993, 26, 98. (f) Thuong, N. T.; Hélène, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 666. (g) Reference 2b.
20. For DNA scission by artificial nucleases, see: (a) Dervan, P. B. Science 1986, 232, 464. (b) Moser, H. E.; Dervan, P. B. Science 1987, 238, 645. (c) Sigman, D. S.; Chen, C. B. Annu. Rev. Biochem. 1990, 59, 207. (d) Nielsen, P. E. Bioconjugate Chem. 1991, 2, 1. (e) Sigman, D. S.; Bruice, T. W.; Mazumder, A.; Sutton, C. L. Acc. Chem. Res. 1993, 26, 98. (f) Thuong, N. T.; Hélène, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 666. (g) Reference 2b.
21. For DNA scission by artificial nucleases, see: (a) Dervan, P. B. Science 1986, 232, 464. (b) Moser, H. E.; Dervan, P. B. Science 1987, 238, 645. (c) Sigman, D. S.; Chen, C. B. Annu. Rev. Biochem. 1990, 59, 207. (d) Nielsen, P. E. Bioconjugate Chem. 1991, 2, 1. (e) Sigman, D. S.; Bruice, T. W.; Mazumder, A.; Sutton, C. L. Acc. Chem. Res. 1993, 26, 98. (f) Thuong, N. T.; Hélène, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 666. (g) Reference 2b.
22. For DNA scission by artificial nucleases, see: (a) Dervan, P. B. Science 1986, 232, 464. (b) Moser, H. E.; Dervan, P. B. Science 1987, 238, 645. (c) Sigman, D. S.; Chen, C. B. Annu. Rev. Biochem. 1990, 59, 207. (d) Nielsen, P. E. Bioconjugate Chem. 1991, 2, 1. (e) Sigman, D. S.; Bruice, T. W.; Mazumder, A.; Sutton, C. L. Acc. Chem. Res. 1993, 26, 98. (f) Thuong, N. T.; Hélène, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 666. (g) Reference 2b.
23. (a) Uhlmann, E.; Peyman, A. Chem. Rev. 1990, 90, 543.
24. (b) Goodchild, J. Bioconjugate Chem. 1990, 1, 165.
25. Diastereoselective synthesis of a phosphoramidite monomer of dinucleotide, which has a reactive residue on the phosphorus atom, was reported: Endo, M.; Komiyama, M. J. Org. Chem. 1996, 61, 1994 and references therein.
26. Yoshinari, K.; Yamazaki, K.; Komiyama, M. J. Am. Chem. Soc. 1991, 113, 5899.
27. Fidanza, J. A.; McLaughlin, L. W. J. Org. Chem. 1992, 57, 2340.
28. The selective hydrolysis was accompanied by some additional scissions near the 3′-end. Assumedly. These linkages are activated for alkaline hydrolysis on the hetero-duplex formation.
29. Alien, F. S.; Gray, D. M.; Roberts, G. P.; Tinoco, I., Jr. Biopolymers 1972, 11, 853.
30. 3 than the U11-p-U12 linkage (the latter linkage is another scission site). Probably, structural changes of the strand around the X-residue cannot be satisfactorily reproduced by the present calculation.
31. a values of free ethylenediamine are 6.7 and 9.5, they can be increased by negative charges of the DNA and RNA when the artificial ribonucleases form heteroduplexes with the substrate RNA. Here, the acid-base cooperation cannot operate.
32. a values of diethylenetriamine are 4.6, 8.6, and 9.7, as determined by potentiometric titration (protonation of the central amine is greatly suppressed by the electrostatic repulsion by the neighboring two positive charges).
33. Gait, M. J.; Pritchard, C.; Slim, G. Oligonucleotides and Analogues; Eckstein, F., Ed.; IRL Press: Oxford, 1991; p 25.