First synthesis of H-phosphonate oligonucleotides bearing N-unmodified bases

Tetrahedron Letters

Volumn 40, Issue 5, 1999, Pages 915-918

  Wada, Takeshi ^a   Honda, Fumio ^a   Sato, Yuichi ^a   Sekine, Mitsuo ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Nucleic acids; Solid phase synthesis

Indexed keywords

DNA; OLIGONUCLEOTIDE;

ARTICLE; CONFORMATIONAL TRANSITION; DNA SYNTHESIS; MOLECULAR STABILITY; NUCLEOTIDE METABOLISM; NUCLEOTIDE SEQUENCE;

EID: 0033613759     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02481-2     Document Type: Article

References (20)

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9. PH = 614.0 Hz) were observed. These products must be formed via the thymidine 3′,5′-cyclic H-phosphonate. However, the highly strained 3′,5′- cyclic nucleotide may be quickly hydrolyzed by traces of water existing in the solvent to give the H-phosphonate monoesters.
10. Agrawal S. In: Agrawal S. editor. Protocols for Oligonucleotide Conjugates, Synthesis and Analytical Techniques. Methods in Molecular Biology. Totowa: Humana Press, 1994;26:93-120.
11. 31P NMR.
12. Osward AA. Can. J. Chem. 1959;37:1498-1504. Nifant'ev ÉE, Nasonovski IS, Borisenko AA. Zh. Obsh. Khim. 1970;40:1248-1251. ibid. idem. 1971;41:2368-2371.
13. Osward AA. Can. J. Chem. 1959;37:1498-1504. Nifant'ev ÉE, Nasonovski IS, Borisenko AA. Zh. Obsh. Khim. 1970;40:1248-1251. ibid. idem. 1971;41:2368-2371.
14. Osward AA. Can. J. Chem. 1959;37:1498-1504. Nifant'ev ÉE, Nasonovski IS, Borisenko AA. Zh. Obsh. Khim. 1970;40:1248-1251. ibid. idem. 1971;41:2368-2371.
15. 3 (1:4, v/v).
16. Pyridine containing 1% of TFA was used as a solvent to suppress the N-phosphonylation of deoxycytidine with 9 and BOMP.
17. 5: 1455.12. Found 1455.09.
18. 4OAc (pH 7.0) at 50 °C was used for HPLC. Further efforts should be made to isolate H-phosphonate oligonucleotides without decomposition.
19. Wada T, Mochizuki A, Sato Y, Sekine M. Tetrahedron Lett. 1998;39:7123-7126.
20. 11: 3165.29. Found 3165.25.