The synthesis of oligoribonucleotides containing N6-alkyladenosines and 2-methylthio-N6-alkyladenosines via post-synthetic modification of precursor oligomers

Nucleic Acids Research

Volumn 31, Issue 15, 2003, Pages 4461-4471

  Kierzek, Elzbieta ^a   Kierzek, Ryszard ^a  

^a INSTITUTE OF BIOORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

6 METHYLTHIOINOSINE; ADENOSINE DERIVATIVE; NUCLEOSIDE; OLIGOMER; OLIGORIBONUCLEOTIDE; PROTEIN PRECURSOR; TRANSFER RNA; 2 METHYLTHIOADENOSINE; 2-METHYLTHIOADENOSINE; ADENOSINE; AMINE; DRUG DERIVATIVE; OLIGONUCLEOTIDE; ORGANOPHOSPHORUS COMPOUND; PHOSPHORAMIDOUS ACID; PURINE NUCLEOSIDE; SULFOXIDE;

ANTICODON; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL PROCEDURES; CONTROLLED STUDY; OXIDATION; PRIORITY JOURNAL; RNA TRANSLATION; STRUCTURE ANALYSIS; SYNTHESIS; ALKYLATION; CHEMISTRY; OXIDATION REDUCTION REACTION;

ADENOSINE; ALKYLATION; AMINES; METHYLTHIOINOSINE; OLIGONUCLEOTIDES; OLIGORIBONUCLEOTIDES; ORGANOPHOSPHORUS COMPOUNDS; OXIDATION-REDUCTION; PURINE NUCLEOSIDES; SULFOXIDES; THIONUCLEOSIDES;

EID: 0041660918     PISSN: 03051048     EISSN: None     Source Type: Journal    
DOI: 10.1093/nar/gkg632     Document Type: Article

References (41)

1. Limbach,P.A., Crain,P.F. and McClosky,J.A. (1994) Summary: the modified nucleosides of RNA. Nucleic Acids Res., 22, 2183-2196.
2. Bjork,G.R. (1995) tRNA: structure, biosynthesis and function. In Soll,D. and RajBhandary,U. (eds.), Biosynthesis and Function of Modified Nucleosides. ASM Press, Washington, DC, pp. 165-206.
3. Persson,B.C. (1993) Modification of tRNA as a regulatory device. Mol. Microbiol., 8, 1011-1016.
4. Grosjean,H., Houssier,C., Romby,P. and Marquet,R. (1998) Modulatory role of modified nucleotides in RNA loop-loop interaction. In Grosjean,H. and Benne,R. (eds.), Modification and Editing of RNA. ASM Press, Washington DC, pp. 113-133.
5. Lys stabilize a canonical U-turn structure. Biochemistry, 39, 12575-12584.
6. Agris,P.F., Sierzputowska-Gracz,H., Smith,W., Malkiewicz,A., Sochacka,E. and Nawrot,B. (1992) Thiolation of uridine carbon-2 restricts the motional dynamics of the transfer RNA wobble position nucleoside. J. Am. Chem. Soc., 114, 2652-2656.
7. +2 in RNA structure and function. Prog. Nucleic Acid Res. Mol. Biol., 53, 79-129.
8. Grasby,J.A. and Gait,M.J. (1994) Synthetic oligoribonucleotides carrying site-specific modifications for RNA structure-function analysis. Biochimie, 76, 1223-1234.
9. Adamiak,R.W., Biala,E., Grzeskowiak,K., Kierzek,R., Kraszewski,A., Markiewiez,W.T., Okupniak,J., Stawinski,J. and Wiewiorowski,M. (1978) The chemical synthesis of the anticodon loop of an eukaryotic initiator tRNA containing the hypermodified nucleoside N-(N-threonylcarbamoyl)adenosine. Nucleic Acids Res., 5, 1889-1905.
10. Lys anticodon loop fragment and its analogues. Nucl. Nucl., 17, 327-338.
11. 6A. Biochemistry, 39, 13396-13404.
12. Met containing N-{[9-(β-D-ribofuranosyl)-9H-purin-6-yl]carbamoyl)-L-threonine. Helvetica Chim. Acta, 83, 152-161.
13. 6A and pseudouridine using phosphoramidite chemistry. J. Org. Chem., 65, 5609-5614.
14. 6-isopentenyladenosine and its 2-methylthio analogue into oligoribonucleotides. Nucleic Acids Res. Symp. Ser., 18, 105-108.
15. Swiderski,P., Antkowiak,W.Z. and Adamiak,R.W. (1991) First, solid-support-aided introduction of isopentenyladenosine. Hypermodified nucleoside of tRNA into oligoribonucleotide chain. Nucl. Nucl., 10, 599-600.
16. 6A) on thermal stability of RNA duplexes. Biophys. Chem., 91, 135-140.
17. 6-alkyladenosines. Nucleic Acids Res., 31, 4472-4480.
18. Robins,M.J. and Uznañski,B. (1981) Nucleic acid related compounds. 33. Conversions of adenosine and guanosine to 2,6-dichloro, 2-amino-6-chloro, and derived purine nucleosides. Can. J. Chem., 59, 2601-2606.
19. Cava,M.P. and Levinson,M.J. (1985) Thionation reactions of Lawesson's reagents. Tetrahedron, 41, 5061-5087.
20. Morisawa,H., Utagawa,T., Miyoshi,T., Yoshinaga,F., Yamazaki,A. and Mitsugi,K. (1980) A new method for synthesis of some 9-β-D-arabinofuranosylpurines by a combination of chemical and enzymatic reactions. Tetraherdon Lett., 21, 479-482.
21. Wetzel,R. and Eckstein,F. (1975) Synthesis and reactions of 6-methylsulfonyl-9-β-D-ribofuranosylpurine. J. Org. Chem., 40, 658-660.
22. Smith,M., Rammler,D.H., Goldberg,I.H. and Khorana,H.G. (1962) Studies on polynucleotides. XIV. Specific synthesis of the C3′-C5′ interribonucleotide linkage. Synthesis of uridyl-(3′-5′)-uridine and uridyl-(3′-5′ )-adenosine. J. Am. Chem. Soc., 84, 430-440.
23. Usman,N., Ogilvie,K.K., Jiang,M.-Y. and Cedergren,R.J., (1987) Automated chemical synthesis of long oligoribonucleotides using 2′-O-silylated ribonucleoside 3′-O-phosphoramidites on a controlled-pore glass support: synthesis of a 43-nucleotide sequence similar to the 3′-half molecule of an E.coli formylmethionine tRNA. J. Am. Chem. Soc., 109, 7845-7854.
24. Xia,T., SantaLucia,J.,Jr, Burkard,M.E., Kierzek,R., Schroeder,S.J., Jiao,X., Cox,C. and Turner,D.H. (1998) Parameters for expended nearest-neighbor model for formation of RNA duplexes with Watson-Crick base pair. Biochemistry, 37, 14719-14735.
25. 4-alkylthymine. Nucleic Acids Res., 18, 4061-4065.
26. MacMillan,A.M. and Verdine.G.L. (1991) Engineering tethered DNA molecules by the convertible nucleoside approach. Tetrahedron, 47, 2603-2616.
27. 4-(dimethylamino)-5-methylcytosine and 4-thiothymine. J. Org. Chem., 57, 3839-3845.
28. Xu,Y-Z, Zhang,Q. and Swann,P.F. (1992) Synthesis by post-synthetic substitution of oligomers containing guanine modified at 6-position with S-, N, O-derivatives. Tetrahedron, 48, 1729-1740.
29. Gao,H., Fathi,R., Gaffney,B.L., Goswami,B., Kung,P-P., Rhee,Y., Jin,R. and Jones,R.A. (1992) 6-O-(Pentaflurorphenyl)-2′-deoxyguanosine: a versatile synthon for nucleoside and oligonucleotide synthesis. J. Org. Chem., 57, 6954-6959.
30. Xu,Y.-Z., Zhang,Q. and Swann,P.F. (1992) Synthesis and duplex stability of oligodeoxynucleotides containing 6-mercaptopurine. Tetrahedron Lett., 33, 5837-5840.
31. Coleman,R.S. and Kesicki,E.A. (1994) Synthesis and postsynthetic modification oligodeoxynucleodides containing 4-thio-2′-deoxyuridine. J. Am. Chem. Soc., 116, 11636-11642.
32. Wayne,C. and Robins.R.K. (1959) Potential purine antagonists. XX. The preparation and reactions of some methylthiopurines. J. Am. Chem. Soc., 81, 5997-6007.
33. Villar,J.D.F. and Motta,M.A. (2000) Syjithesis of 6-alkyl and arylamino-9-(tetrahydro-2-pyranyl)purines via 6-methylsulfonylpurine. Nucl. Nucl. Nucleic Acids, 19, 1005-1015.
34. Burdzy,A., Skalski,B., Biala,E., Kowalewski,A., Paszyc,S. and Adamiak,R.W. (1995) Post-synthetic transformations of oligodeoxynucleotides originated at 6-methylthiopurine site. Nucl. Nucl., 14, 979-982.
35. McBride,L.J. and Caruthers,M.H. (1983) An investigation of several deoxynucleosides phosphoramidites useful for synthesizing oligodeoxynucleotides. Tetrahedron Lett., 24, 245-249.
36. 6-Isopentenyladenosine: chemical reactions, biosynthesis, metabolism and significance to the structure and function of tRNA. Prog. Nucleic Acid Res. Mol. Biol., 10, 57-86.
37. 6-isopentenyladenosine and oligoribonucleotides containing this modification. PhD thesis. Adam Mickiewicz University, Poznañ, Poland.
38. Hecht,S.M., Helgeson,J.P. and Fujii,T. (1968) Combination of 6-chloropurine with primary amine. In Zorbach,W.W. and Tipson,R.S. (eds.), Synthetic Procedures in Nucleic Acids Chemistry. Wiley and Sons, New York, NY, pp. 8-10.
39. Ikehara,M. and Uno,H. (1965) Futher studies on the chlorination of inosine derivatives with dimethylformamide-thionyl chloride complex. Chem. Pharm. Bull., 13, 221-223.
40. Nair,V. and Hattrick,B.J. (1988) Sulfone of the antibiotic, nebularine: synthesis and conversion to novel analogues of nebularine. Tetrahedron, 44, 7001-7006.
41. 1 receptor. Tetrahedron, 49, 2169-2184.