Diastereomerically pure nucleoside-5′-O-(2-thio-4,4-pentamethylene-1, 3,2-oxathiaphospholane)s-Substrates for synthesis of P-chiral derivatives of nucleoside-5′-O-phosphorothioates

Chirality

Volumn 23, Issue 3, 2011, Pages 237-244

  Tomaszewska, Agnieszka ^a   Guga, Piotr ^a   Stec, Wojciech J ^a  

^a CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

Author keywords

HPLC; nucleoside thiophosphates; oxathiaphospholane monomers; P diastereomers; stereoselectivity

Indexed keywords

NUCLEOSIDE 5' O (2 THIO 4,4 PENTAMETHYLENE 1,3,2 OXATHIAPHOSPHOLANE) DERIVATIVE; NUCLEOSIDE 5' O PHOSPHOROTHIOATE DERIVATIVE; NUCLEOSIDE DERIVATIVE; PHOSPHATE; PHOSPHONIC ACID DERIVATIVE; PHOSPHOROTHIOIC ACID DERIVATIVE; PHOSPHOROUS ACID; RIBONUCLEOSIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DIASTEREOISOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEOXYRIBONUCLEOSIDES; DINUCLEOSIDE PHOSPHATES; HYDROLYSIS; NUCLEOSIDES; NUCLEOTIDES; ORGANIC CHEMISTRY PROCESSES; PHOSPHOROTHIOATE OLIGONUCLEOTIDES; RIBOSE; STEREOISOMERISM; THYMIDINE;

EID: 79951478655     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20905     Document Type: Article

References (30)

1. Biggs J, Hersperger E, Steeg PS, Liotta LA, Shearn A,. A Drosophila gene that is homologous to a mammalian gene associated with tumor metastasis codes for a nucleoside diphosphate kinase. Cell 1990; 63: 933-940. (Pubitemid 120034934)
2. Bominaar AA, Molijin AC, Pestel M, Veron M, Van HPJ,. Activation of G-proteins by receptor-stimulated nucleoside diphosphate kinase in Dictyostelium. EMBO J 1993; 12: 2275-2279. (Pubitemid 23194177)
3. Steeg PS, Bevilacqua G, Kopper L, Thorgeirsson UP, Talmadge JE, Liotta LA, Sobel ME,. Evidence for a novel gene associated with low tumor metastatic potential. J Natl Cancer Inst 1988; 80: 200-204.
4. Sanger F, Nicklen S, Coulson AR,. DNA sequencing with chain-terminating inhibitors. Proc Natl Acad Sci USA 1977; 74: 5463-5467.
5. Eckstein F,. Phosphorothioate analogues of nucleotides-tools for the investigation of biochemical processes. Angew Chem Int Ed Engl 1983; 22: 423-439. (Pubitemid 13576177)
6. Eckstein F,. Nucleoside phosphorothioates. Annu Rev Biochem 1985; 54: 367-402. (Pubitemid 15073651)
7. Micklefield J,. Backbone modification of nucleic acids: synthesis, structure and therapeutic applications. Curr Med Chem 2001; 8: 1157-1179. (Pubitemid 32655075)
8. Corradini R, Sforza S, Tedeschi T, Marchelli R,. Chirality as a tool in nucleic acid recognition: principles and relevance in biotechnology and in medicinal chemistry. Chirality 2007; 19: 269-294. (Pubitemid 46659341)
9. Stein CA, Krieg AM, editors. Applied antisense oligonucleotide technology. NewYork: Wiley; 1998.
10. Eckstein F,. Phosphorothioate oligodeoxynucleotides: what is their origin and what is unique about them? Antisense Nucleic Acid Drug Dev 2000; 10: 117-121. (Pubitemid 30255596)
11. Wang L, Chen S, Xu T, Taghizadeh K, Wishnok JS, Zhou X, You D, Deng Z, Dedon PC,. Phosphorothioation of DNA in bacteria by dnd genes. Nat Chem Biol 2007; 3: 709-710. (Pubitemid 47609115)
12. Frey PA, Sammons RD,. Bond order and charge localization in nucleoside phosphorothioates. Science 1985; 228: 541-545.
13. Sheu KF, Richard JP, Frey PA,. Stereochemical courses of nucleotidyltransferase and phosphotransferase action. Uridine diphosphate glucose pyrophosphorylase, galactose-1-phosphate uridylyl transferase, adenylate kinase, and nucleoside diphosphate kinase. Biochemistry 1979; 18: 5548-5556.
14. 18O] triphosphate and the mechanistic consequences for the reactions catalyzed by glycerol kinase, hexokinase, pyruvate kinase, and acetate kinase. Biochemistry 1979; 18: 3927-3933.
15. Owczarek A, Kaczmarek R, Mikołajczyk B, Wasilewska E, Korczyński D, Baraniak J, Koziołkiewicz M, Stec WJ, Brenner C,. Stereochemical analysis of diastereomeric 1,3-bis(adenosine-5′-O- phosphorothioyl)glycerols. Nucleosides Nucleotides Nucleic Acids 2003; 22: 797-799.
16. Stec WJ, Karwowski B, Boczkowska M, Guga P, Koziołkiewicz M, Sochacki M, Wieczorek M, Błaszczyk J,. Deoxyribonucleoside 3′-O-(2-thio- and 2-oxo-"spiro"-4,4-pentamethylene-1,3,2- oxathiaphospholane)s: monomers for stereocontrolled synthesis of oligo(deoxyribonucleoside phosphorothioate)s and chimeric PS/PO oligonucleotides. J Am Chem Soc 1998; 120: 7156-7167. (Pubitemid 28389340)
17. Guga P, Stec WJ,. Synthesis of phosphorothioate oligonucleotides with stereodefined phosphorothioate linkages. In:, Beaucage SL, Bergstrom DE, Glick GD, Jones RA, editors. Current protocols in nucleic acid chemistry, Hoboken, NJ: Wiley; 2003. p 4.17.1-4.17.28.
18. Misiura K, Szymanowicz D, Stec WJ,. Synthesis of nucleoside α-thiotriphosphates via an oxathiaphospholane approach. Organic Lett 2005; 7: 2217-2220. (Pubitemid 40826088)
19. Misiura K, Szymanowicz D, Olesiak M, Stec WJ,. DBU-assisted 1,3,2-oxathiaphospholane ring-opening condensation with selected O-, S-, N- and C-nucleophiles. Tetrahedron Lett 2004; 45: 4301-4305. (Pubitemid 38610070)
20. Okruszek A, Olesiak M, Balzarini J,. The synthesis of nucleoside 5′-O-(1,1-dithiotriphosphates). J Med Chem 1994; 37: 3850-3854.
21. Iyer RP, Egan W, Regan JB, Beaucage SL,. 3H-1,2-Benzodithiole-3-one 1,1-dioxide as an improved sulfurizing reagent in the solid-phase synthesis of oligodeoxyribonucleoside phosphorothioates. J Am Chem Soc 1990; 112: 1253-1254. (Pubitemid 20127085)
22. Eckstein F, Potter BVL, Connolly B,. Synthesis and configurational analysis of a dinucleoside phosphate isotopically chiral at phosphorus. Stereochemical course of Penicillium citrinum nuclease P1 reaction. Biochemistry 1983; 22: 1369-1377. (Pubitemid 13084558)
23. Griffiths AD, Potter BVL, Eperon IC,. Stereospecificity of nucleases towards phosphorothioate-substituted RNA: stereochemistry of transcription by T7 RNA polymerase. Nucleic Acids Res 1987; 15: 4145-4162.
24. Spartan'06 Wavefunction, Inc, 2006. Available at:.
25. Gaussian 03, Rev. D.01. Wallingford, CT: Gaussian, Inc.; 2004.
26. Stec WJ, Wilk A,. Stereokontrollierte synthese von oligonucleosidphosphorothioaten. Angew Chem 1994; 106: 747-761.
27. Stec WJ, Wilk A,. Stereocontrolled synthesis of oligo(nucleoside phosphorothioate)s. Angew Chem Int Ed Engl 1994; 33: 709-722. (Pubitemid 24987153)
28. Stec WJ, Grajkowski A, Karwowski B, Koziołkiewicz M, Misiura K, Okruszek A, Wilk A, Guga P, Boczkowska M,. Diastereomers of nucleoside 3′-O-(2-thio-1,3,2-oxathia(selena)phospholanes): building blocks for stereocontrolled synthesis of oligo(nucleoside phosphorothioate)s. J Am Chem Soc 1995; 117: 12019-12029. (Pubitemid 26022768)
29. Misiura K, Szymanowicz D, Stec WJ,. Synthesis and chemical and enzymatic reactivity of thymidine 3′-O- and 5′-O-phosphorofluoridothioates. Chem Commun 1998; 515-516. (Pubitemid 128675324)
30. Ludwig J, Eckstein F,. Rapid and efficient synthesis of nucleoside 5′-O-(1-thiotriphosphates), 5′-triphosphates and 2′,3′-cyclophosphorothioates using 2-chloro-4H-1,3,2- benzodioxaphosphorin-4-one. J Org Chem 1989; 54: 631-635. (Pubitemid 19060209)