A new odorless procedure for the synthesis of 2'-deoxy-6-thioguanosine and its incorporation into oligodeoxynucleotides

Nucleosides, Nucleotides and Nucleic Acids

Volumn 28, Issue 8, 2009, Pages 752-760

  Onizuka, Kazumitsu ^a,b   Taniguchi, Yosuke ^a,b   Sasaki, Shigeki ^a,b  

^a KYUSHU UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

2' Deoxy 6 thioguanosine; 2 Ethylhexyl 3 mercaptopropionate; DNA synthesis; Odorless synthesis; Phosphoroamidite

Indexed keywords

2 [(2 ETHYLHEXYL)OXYCARBONYL]ETHYL] 3',5' O BIS(TERT BUTYLDIMETHYLSILYL) 2' DEOXY 6 THIOGUANOSINE; 2 ETHYLHEXYL 3 MERCAPTOPROPIONATE; 6 O MESITYLENESULFONYL DERIVATIVE; DEOXYTHIOGUANOSINE; OLIGODEOXYNUCLEOTIDE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; DEPROTECTION REACTION; DESULFURIZATION; DNA SYNTHESIS; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEOXYGUANOSINE; GUANOSINE; MOLECULAR STRUCTURE; ODORS; OLIGODEOXYRIBONUCLEOTIDES; ORGANOPHOSPHORUS COMPOUNDS; THIONUCLEOSIDES;

EID: 75149167416     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770903155576     Document Type: Article

References (20)

1. Lencastre, A.D.; Hamill, S.; Pyle, A.M. A single active-site region for a group II intron. Nat. Struct. Mol. Biol. 2005, 12, 626-627.
2. Christian, E.L.; McPheeters, D.S.; Harris, M.E. Identification of individual nucleotides in the bacterial ribonuclease P ribozyme adjacent to the pre-tRNA cleavage site by short-range photo-crosslinking. Biochemistry 1998, 37, 17618-17628.
3. Wang, Z.; Rana, T.M. RNA-protein interactions in the Tat-trans-activation response element complex determined by site-specific photo-cross-linking. Biochemistry 1998, 37, 4235-4243.
4. Nikiforov, T.T.; Connolly, B.A. Oligodeoxynucleotides containing 4-thiothymidine and 6- thiodeoxyguanosine as affinity labels for the Eco RV restriction endonuclease and modification methylase. Nucleic Acids Res. 1992, 20, 1209-1214.
5. Coleman, R.S.; Siedlcki, J.M. Synthesis of a 4-thio-2′- deoxyuridine-containing oligonucleotide. Development of the thiocarbonyl group as a linker element. J. Am. Chem. Soc. 1992, 114, 9229-9230.
6. Coleman, R.S.; Kesicki, E.A. Synthesis and postsynthetic modification of oligodeoxynucleotides containing 4-thio-2′-deoxyuridine (ds4U). J. Am. Chem. Soc. 1994, 116, 11636-11642.
7. Coleman, R.S.; Pires, R.M. Covalent cross-linking of duplex DNA using 4-thio-2′-deoxyuridine as a readily modifiable platform for introduction of reactive functionality into oligonucleotides. Nucleic Acids Res. 1997, 25, 4771-4777.
8. Ali, M.M.; Alam, M.R.; Kawasaki, T.; Nakayama, S.; Nagatsugi, F.; Sasaki, S. Sequence- and basespecific delivery of nitric oxide to cytidine and 5-methylcytidine leading to efficient deamination. J. Am. Chem. Soc. 2004, 126, 8864-8865.
9. Ali, M.M.; Nagatsugi, F.; Nakayama, S.; Alam, M.R.; Kawasaki, T.; Sasaki, S. Design of high efficient and selective transfer reaction of nitrosyl group to dC and dmC resulting in specific deamination. Nucleosides, Nucleotides, and Nucleic Acids 2005, 24, 721-724.
10. Onizuka, K.; Taniguchi, Y.; Sasaki, S. Site-specific covalent modification of RNA guided by functionality-transfer oligodeoxynucleotides. Bioconjugate Chem. 2009, 20, 779-803.
11. Onizuka, K.; Taniguchi, Y.; Sasaki, S. Development of novel thioguanosine analogs with the ability to specifically modified cytidine. Nucleic Acids Symp. Series 2007, 51, 5-6.
12. Christopherson, M.S.; Broom, A.D. Synthesis of oligonucleotides containing 2′-deoxy-6- thioguanosine at a predetermined site. Nucleic Acids Res. 1991, 19, 5719-5724.
13. Adams, C.J.; Farrow, M.A.; Murray, J.B.; Kelly, S.M.; Price, N.C.; Stockley, P.G. Incorporation of 6- thioinosine into oligoribonucleotides. Tetrahedron Lett. 1995, 36, 5421-5424.
14. Rao, T.S.; Jayaraman, K.; Durland, R.H.; Revankar, G.R. A novel synthesis of S6-cyanoethyl-2′ - deoxythioguanosine and its incorporation into triple helix forming oligonucleotides. Tetrahedron Lett. 1992, 33, 7651-7654.
15. Rao, T.S.; Durland, R.H.; Seth, D.M.; Myrick, M.A.; Bodepudi, V.; Revankar, G.R. Incorporation of 2′-deoxy-6-thioguanosine into G-rich oligodeoxyribonucleotides inhibits G-tetrad formation and facilitates triplex formation. Biochemistry 1995, 34, 765-772.
16. Kadokura, M.; Wada, T.; Seio, K.; Sekine, M. Synthesis of 4-thiouridine, 6-thioinosine, and 6- thioguanosine 3′,5′ -O-bisphosphates as donor molecules for RNA ligation and their application to the synthesis of photoactivatable TMG-capped U1 snRNA fragments. J. Org. Chem. 2000, 65, 5104-5113.
17. Wang, Y.; Lattmann, E.; Zheng, Q. Preparation of 6-thioguanosine phosphoramidite for oligoribonucleotide synthesis. Nucleosides, Nucleotides, and Nucleic Acids 2003, 22, 1247-1249.
18. Zheng, Q.; Wang, Y.; Lattmann, E. Synthesis of S6-(2,4-dinitrophenyl)-6- thioguanosine phosphoramidite and its incorporation into oligoribonucleotides. Bioorg. Med. Chem. Lett. 2003, 13, 3141-3144.
19. Itoh, T.; Mase, T. A general palladium-catalyzed coupling of aryl bromides/triflates and thiols. Org Lett. 2004, 6, 4587-4590.
20. Itoh, T.; Mase, T. Practical thiol surrogates and protective groups for arylthiols for Suzuki-Miyaura conditions. J. Org. Chem. 2006, 71, 2203-2206.