Facile synthesis of puromycin-tethered oligonucleotides at the 3'-end

Tetrahedron Letters

Volumn 39, Issue 33, 1998, Pages 5975-5978

  Ikeda, Shuji ^a   Saito, Isao ^a   Sugiyama, Hiroshi ^b  

^a KYOTO UNIVERSITY   (Japan)

^b TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

OLIGOMER; OLIGONUCLEOTIDE; PUROMYCIN;

ARTICLE; DNA SYNTHESIS; GEL ELECTROPHORESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; POLYMERASE CHAIN REACTION; PROTEIN SYNTHESIS INHIBITION; RNA SYNTHESIS; RNA TRANSLATION;

EID: 0032514441     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01226-X     Document Type: Article

References (20)

1. 1. Abbreviations: LCAA-CPG (Long Chain Alkyl Amine Controlled Pore Glass), Fmoc-OSu(N(9-Fluorenyl-methoxycarbonyloxy)succinimide), DMTrCl(Dimethoxytrityl chloride), DMAP (4-Dimethylaminopyridine), DEC (1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide), DhbtOH (3,4-Dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine), AP (Alkaline phosphatase), s. v. PDE (snake venom phosphodiesterase).
2. 2. Mainwaring, W. I. P.; Parish, J. H.; Pickering, J. D.; Mann, N. H. (1982) Nucleic Acid Biochemistry and Molecular Biology p 20, 211 Blackwell Scientific Publications.
3. 3. Green, R.; Switzer, C.; Noller, H. F. Science 1998, 280, 286.
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5. (b) Roberts, R. W.; Szostak, J. W. Proc. Natl. Acad. Sci. USA 1997, 97, 12297.
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8. (c) Uemura, H.; Imai, M ; Ohtsuka, E.; Ikehara, M.; Söll, D. Nucleic Acids Res. 1982, 10, 20, 6531.
9. (d) Heckler, T. G.; Zama, Y.; Naka, T.; Hecht, S. M. J. Biol. Chem. 1983, 258, 7, 4492
10. (e) Palsen, H.; Wintermeyer, W. Eur. J. Biocem. 1984 138, 117.
11. 6. Part of the synthesis of Pu-tethered oligonucleotides at the 3' end was presented at the following meetings, (a) Ikeda S.; Sugiyama H.; and Saito I. The 68th Annual Meeting of Chemical Society of Japan, Tokyo, March, 1997.
12. (b) Ikeda S.; Sugiyama H.; and Saito I. The 214th American Chemical Society National Meeting, Nevada, Sep., 1997.
13. +], found 1096.
14. 8. Walsh, A. J.; Clark, G. C.; Fraser, W. Tetrahedron Lett. 1997, 38, 1651.
15. 10 such as triethylamine in pyridine, the Fmoc group of 3 was partially released.
16. 10.Damha, M. J.; Giannaris, P. A.; Zabarylo, S. V. Nucleic Adds Res. 1990, 18, 3813.
17. 4OH/MeOH at 55 °C for 17 h. Subsequently, 0.4 mL of tetrabutylammonium fluoride solution was added to the residue. The resulting suspension was shaken at room temperature for 6 h and then extracted with ethyl acetate. The aqueous layer was concentrated and subjected to reverse-phase HPLC.
18. 12. Enzymatic digestion of oligomers. To a solution of oligomer in 50 mM sodium cacodylate buffer (pH 7.0) were added s.v. PDE (0.3 unit/ml, final concentration) and calf intestine AP (100 unit/ml, final concentration). The solution was incubated at 37 °C for 12 h and was analyzed by reverse-phase HPLC.
19. +) found 774.2.
20. 20-Pu calcd 12838.6; found 12849.7.