Gram-scale chemical synthesis of 2'-deoxynucleoside-5'-o-triphosphates

Current Protocols in Nucleic Acid Chemistry

Volumn , Issue SUPPL.49, 2012, Pages

  Kore, Anilkumar R ^a   Shanmugasundaram, Muthian ^a   Senthilvelan, Annamalai ^a   Srinivasan, Balasubramanian ^a  

^a Life Technologies Corporation   (United States)

Author keywords

2' deoxyribonucleotides; Chemical synthesis; dNTP; One pot synthesis; Phosphorylation; Proton sponge; Triphosphate

Indexed keywords

2' DEOXYADENOSINE 5' O TRIPHOSPHATE; 2' DEOXYCYTIDINE 5' O TRIPHOSPHATE; 2' DEOXYGUANOSINE 5' O TRIPHOSPHATE; 2' DEOXYNUCLEOSIDE; 2' DEOXYURIDINE 5' O TRIPHOSPHATE; DEOXYRIBONUCLEOTIDE; PURINE DERIVATIVE; PYRIMIDINE DERIVATIVE; PYROPHOSPHATE; THYMIDINE 5' O TRIPHOSPHATE; THYMIDINE DERIVATIVE; TRIBUTYLAMMONIUM PYROPHOSPHATE; UNCLASSIFIED DRUG; 2'-DEOXYADENOSINE TRIPHOSPHATE; 2'-DEOXYCYTIDINE 5'-TRIPHOSPHATE; DEOXYADENOSINE PHOSPHATE; DEOXYADENOSINE TRIPHOSPHATE; DEOXYCYTIDINE PHOSPHATE; DEOXYCYTIDINE TRIPHOSPHATE; DIPHOSPHORIC ACID; NUCLEOSIDE; PURINE NUCLEOTIDE; PYRIMIDINE NUCLEOTIDE; THYMIDINE 5'-TRIPHOSPHATE; THYMIDINE TRIPHOSPHATE;

ARTICLE; CHEMICAL STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; ONE POT SYNTHESIS; PH; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; CHEMISTRY; SYNTHESIS;

DEOXYADENINE NUCLEOTIDES; DEOXYCYTOSINE NUCLEOTIDES; DIPHOSPHATES; HYDROLYSIS; NUCLEOSIDES; PURINE NUCLEOTIDES; PYRIMIDINE NUCLEOTIDES; THYMINE NUCLEOTIDES;

EID: 84866777077     PISSN: 19349270     EISSN: 19349289     Source Type: Journal    
DOI: 10.1002/0471142700.nc1310s49     Document Type: Article

References (15)

1. Baddiley, J., Michelson, A.M., and Todd, A.R. 1949. Nucleotides. Part II. A synthesis of adenosine triphosphate. J. Chem. Soc. 582-586.
2. Burgess, K. and Cook, D. 2000. Syntheses of nucleoside triphosphates. Chem. Rev. 100:2047-2059.
3. Catson-Wiliams, J., Smith, M., Carrasco, N., and Huang, Z. 2011. Protection-free one-pot synthesis of 2'-deoxynucleoside 5'-triphosphates and DNA polymerization. Org. Lett. 13:4156-4159.
4. Davisson, V.J., Davis, D.R., Dixit, V.M., and Poulter, C.D. 1987. Synthesis of nucleotide-5'-diphosphates from 5'-O-tosyl nucleosides. J. Org. Chem. 52:1794-1801.
5. Franca, L.T.C., Carrilho, E., and Kist, T.B.L. 2002. A review of DNA sequencing techniques. Q. Rev. Biophy. 35:169-200.
6. Gandhi, V.V. and Samuels, D.C. 2011. A review comparing deoxyribonucleoside triphosphate (dNTP) concentrations in the mitochondrial and cytoplasmic compartments of normal and transformed cells. Nucleosides Nucleotides Nucleic Acids 30:317-339.
7. Gillerman, I. and Fischer, B. 2010. An improved one-pot synthesis of nucleoside 5'-triphosphate analogues. Nucleosides Nucleotides Nucleic Acids 29:245-256.
8. Guo, J., Yu, L., Turro, N.J., and Ju, J. 2010. An integrated system for DNA sequencing by synthesis using novel nucleotide analogues. Acc. Chem. Res. 43:551-563.
9. Hoard, D.E. and Ott, D.G. 1965. Conversion of mono- and oligodeoxyribonucleotides to 5'-triphosphates. J. Am. Chem. Soc. 87:1785-1788.
10. Ludwig, J. 1981. A new route to nucleoside 5'-triphosphates. Acta Biochim. Biophys. Acad. Hung. 16:131-133.
11. Ludwig, J. and Eckstein, F. 1989. Rapid and efficient synthesis of nucleoside 5'-O-(1-thiotriphosphates),5'-triphosphates and 2',3'-cyclophosphorothiolates using 2-chloro-4H-1,3,2-benzodioxaphosphorin-4-one. J. Org. Chem. 54:631-635.
12. Moffatt, J.G. 1964. General synthesis of nucleoside 5'-triphosphate. Can. J. Chem. 42:599-604.
13. Niida, H., Shimada, M., Murakami, H., and Nakanishi, M. 2010. Mechanisms of dNTP supply that play an essential role in maintaining genome integrity in eukaryotic cells. Cancer Sci. 101:2505-2509.
14. Simoncsits, A. and Tomasz, J. 1975. Nucleoside 5'-phosphordiamidates, synthesis and some properties. Nucleic Acids Res. 2:1223-1233.
15. Yoshikawa, M., Kato, T., and Takenishi, T. 1967. A novel method for phosphorylation of nucleosides to 5'-nucleotides. Tetrahedron Lett. 50:5065-5068.