Solid-Phase Oligodeoxynucleotide Synthesis: A Two-Step Cycle Using Peroxy Anion Deprotection

Journal of the American Chemical Society

Volumn 125, Issue 44, 2003, Pages 13427-13441

  Sierzchala, Agnieszka B ^b   Dellinger, Douglas J ^b   Betley, Jason R ^a,c   Wyrzykiewicz, Tadeusz K ^b,d   Yamada, Christina M ^a   Caruthers, Marvin H ^a  

^a UNIVERSITY OF COLORADO   (United States)

^b AGILENT LABORATORIES   (United States)

^c Emmbrook   (United Kingdom)

^d ISIS PHARMACEUTICALS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CHEMICAL MODIFICATION; OXIDATION; PH EFFECTS;

NUCLEOTIDES;

OLIGOMERS;

2' DEOXYNUCLEOSIDE 3' PHOSPHORAMIDITE; 5' DIMETHOXYTRITYL DERIVATIVE; ADENINE DERIVATIVE; ANION; BUFFER; CARBONYL DERIVATIVE; CYTOSINE DERIVATIVE; OLIGODEOXYNUCLEOTIDE; PEROXY ANION; PHOSPHITE; PHOSPHORAMIDIC ACID DERIVATIVE; THYMIDINE DERIVATIVE; TRITYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DNA SYNTHESIS; MASS SPECTROMETRY; MELTING POINT; NUCLEOTIDE METABOLISM; OXIDATION; PH; REACTION TIME; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SOLID; THIN LAYER CHROMATOGRAPHY;

ANIONS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA; OLIGONUCLEOTIDES; ORGANOPHOSPHORUS COMPOUNDS; PEROXIDES; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 0242330791     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja030376n     Document Type: Article

References (48)

1. iBu, isobutyryl; DPC, N,N-diphenylcarbamoyl; N-Me-Imid, N-methylimidazole; PAP, 4-(phenylazo)phenyl; Fmol, 9-fluorenylmethyl; PAGE, polyacrylamide gel electrophoresis; EDTA, ethylene-diaminetetraacetic acid.
2. Letsinger, R. L.; Lunsford, W. B. J. Am. Chem. Soc. 1976, 98, 3655-3661.
3. Beaucage, S. L.; Caruthers, M. H. Tetrahedron Lett. 1981, 22, 1859-1862.
4. Matteucci, M. D.; Caruthers, M. H. J. Am. Chem. Soc. 1981, 103, 3186-3191.
5. Ogilvie, K. K.; Theriault, N. Y.; Seifert, J.-M.; Pon, R. T.; Nemer, J. J. Can. J. Chem. 1980, 58, 2686-2693.
6. Sinha, N. D.; Biernat, J.; Koster, H. Tetrahedron Lett. 1983, 24, 5843-5846.
7. Fodor, S. A. Science 1997, 277, 393-395.
8. Lipshutz, R. J.; Fodor, S. P. A.; Gingeras, T. R.; Lockhart, D. J. Nature Genet. Microarray Suppl. 1999, 21, 20-24.
9. Bennett, C. F. Biochem. Pharmacol. 1998, 55, 9-19.
10. Yuen, A.; Halsey, J.; Fisher, G.; Advani, R.; Moore, M.; Saleh, M.; Ritch, P.; Harker, G.; Ahmed, F.; Jones, C.; Polikoff, P.; Keiser, W.; Kwoh, J. ; Holmlund, J.; Dorr, A.; Sikic, B. American Society of Clinical Oncology's 37th Annual Meeting, San Francisco, CA, May 12, 2001.
11. Lacy, J.; Loomis, R.; Cheng, Y.-C. Proc. Assoc. Cancer Res. 2003, 44, Abstract 6438.
12. Cello, J.; Paul, A. V.; Wimmer, E. Science 2002, 297, 1016-1018.
13. Marshall, W. S.; Boymel, J. L. Drug Discovery Today 1998, 3, 34-42.
14. Caruthers, M. H. In Protein Engineering; Oxender, D. L., Fox, C. F., Eds.; Alan R. Liss: New York, 1987; pp 65-70.
15. Ferretti, L.; Karnik, S. S.; Khorana, H. G.; Nassal, M.; Oprian, D. D. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 599-603.
16. Yu. H.; Kono, M.; McKee, T. D.; Oprian, D. D. Biochemistry 1995, 34, 14963-14969.
17. Schaller, H.; Weimann, G.; Lorch, B.; Khorana, H. G. J. Am. Chem. Soc. 1963, 85, 3821-3827.
18. Efcavitch, J. W.; Heiner, C. Nucleosides Nucleotides 1985, 4, 267.
19. Caruthers, M. H. Acc. Chem. Res. 1991, 24, 278-284.
20. Fritz, H. J.; Belagaje, R.; Brown, E.; Fritz, R. H.; Jones, R.; Lees, R. G.; Khorana, H. G. Biochemistry 1978, 17, 1257-1267.
21. Paul, C. H.; Royappa, A. T. Nucleic Acids Res. 1996, 24, 3048-3052.
22. Septak, M. Nucleic Acids Res. 1996, 24, 3053-3058.
23. McGall, G.; Labadie, J.; Brock, P.; Wallraff, G.; Nguyen, T.; Hinsberg, W. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 13555-13560.
24. Temsamani, J.; Kubert, M.; Agrawal, S. Nucleic Acids Res. 1995, 23, 1841-1844.
25. Gao, X.; LeProust, E.; Zhang, H.; Srivannavit, O.; Gulari, E.; Yu, P.; Nishiguchi, C.; Xiang, Q.; Zhou, Z. Nucleic Acids Res. 2001, 29, 4744-4750.
26. Serafinowski, P. J.; Garland, P. B. J. Am. Chem. Soc. 2003, 125, 962-965.
27. McIsaac, J. E., Jr.; Subbaraman, L. R.; Subbaraman, J.; Mulhausen, H. A. ; Behrman, E. J. J. Org. Chem. 1972, 37, 1037-1041.
28. Edwards, J. O.; Pearson, R. G. J. Am. Chem. Soc. 1962, 84, 16-24.
29. Balgobin, N.; Josephson, S.; Chattopadhyaya, J. B. Tetrahedron Lett. 1981, 22, 3667-3670.
30. Letsinger, R. L.; Ogilvie, K. K. J. Org. Chem. 1967, 32, 296-300.
31. Tittensor, J. R. J. Chem. Soc. (C) 1971, 2656-2662.
32. Subbaraman, L. R.; Subbaraman, J.; Behrman, E. J. J. Org. Chem. 1971, 36, 1256-1259.
33. Subbaraman, L. R.; Subbaraman, J.; Behrman, E. J. Biochemistry 1969, 8, 3059-3066.
34. Letsinger, R. L.; Groody, E. P.; Lander, N.; Tanaka, T. Tetrahedron 1984, 40, 137-143.
35. Ball, D. L.; Edwards, J. O. J. Am. Chem. Soc. 1956, 78, 1125-1129.
36. Gryaznov, S. M.; Letsinger, R. L. J. Am. Chem. Soc. 1991, 113, 5876-5877.
37. Although N-trityl protection is common in the peptide field, it has only been used sparingly in nucleic acid synthesis.
38. Gross, E.; Meinhofer, J. The Peptides: Analysis, Synthesis, Biology; Protection of Functional Groups in Peptide Synthesis, Vol. 3; Academic Press: New York. 1987.
39. Schaller, H.; Khorana, H. G. J. Am. Chem. Soc. 1963, 85, 3828-3835.
40. Ti, G. S.; Gaffney, B. L.; Jones, R. A. J. Am. Chem. Soc. 1982, 104, 1316-1319.
41. Caruthers, M. H.; Barone, A. D.; Beaucage, S. L.; Dodds, D. R.; Fisher, E. F.; McBride, L. J.; Matteucci, M.; Stabinsky, Z.; Tang, J.-Y. Methods Enzymol. 1987, 154, 287-313.
42. Scaringe, S. A. Design and Development of New Protecting Groups for RNA Synthesis. Ph.D. Thesis, 1996.
43. Urdea, M. S.; Ku, L.; Horn, T.; Gee, Y. G.; Warner, B. D. Nucleic Acids Symp. Ser. 1984, 16, 257-260.
44. A capping step can always be added for specific applications.
45. McBride, L. J.; Caruthers, M. H. Tetrahedron Lett. 1983, 24, 2953-2956.
46. Froehler, B. C.; Matteucci, M. D. Nucleic Acids Res. 1983, 11, 8031-8036.
47. McBride, L. J.; Kierzek, R.; Beaucage, S. L.; Caruthers, M. H. J. Am. Chem. Soc. 1986, 108, 2040-2048.
48. Koole, L. H.; Moody, H. M.; Broeders, N. L. H. L.; Quaedflieg, P. J. L. M.; Kuijpers, W. H. A.; van Genderen, M. H. P.; Coenen, A. J. J. M.; van der Wal, S.; Buck, H. M. J. Org. Chem. 1989, 54, 1657-1664.