Convenient synthesis of nucleoside-5′-diphosphates from the corresponding ribonucleoside-5′-phosphoroimidazole

Synthetic Communications

Volumn 36, Issue 22, 2006, Pages 3393-3399

  Kore, Anilkumar R ^a   Parmar, Gaurang ^a  

^a APPLIED BIOSYSTEMS   (United States)

Author keywords

5 phosphoroimidazolide of nucleosides; Nucleoside 5 diphosphate; Tributylammonium orthophosphate; Zinc chloride

Indexed keywords

ADENOSINE DIPHOSPHATE; CYTIDINE DIPHOSPHATE; GUANOSINE DIPHOSPHATE; IMIDAZOLE DERIVATIVE; NUCLEOSIDE DERIVATIVE; RIBONUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG; URIDINE 5 DIPHOSPHATE;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHROMATOGRAPHY; DEPROTECTION REACTION; PURIFICATION; ROOM TEMPERATURE; SYNTHESIS;

EID: 33751115200     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910600941448     Document Type: Article

References (16)

1. Scheit, K. H. Nucleotide Analogs, Synthesis and Biological Function; Wiley: New York, 1980; Chapter 4, pp. 96-141, and Chapter 6, pp. 195-210.
2. Moffatt, J. G.; Khorana, H. G. Nucleoside polyphosphates, VIII: New and improved syntheses of uridine diphosphate glucose and flavin adenine dinucleotide using nucleoside-5′-phosphoramidates. J. Am. Chem. Soc. 1958, 80, 3756-3761.
3. Lohrmann, R.; Khorana, H. G. The use of 2,4,6-triisopropylbenzenesulfonyl chloride for the synthesis of internucleotide bonds. J. Am. Chem. Soc. 1966, 88, 829-833.
4. Moon, M. W.; Khorana, H. G. The use of mesitoyl chloride in the synthesis of internucleotide bonds. J. Am. Chem. Soc. 1966, 88, 1805.
5. Michelson, A. M. Polynucleotides, part I: Synthesis and properties of some polyribonucleotides. J. Chem. Soc. 1959, 1371.
6. Baddiley, J.; Michelson, A. M.; Todd, A. R. Nucleosides, part II: A synthesis of adenosine triphosphate. J. Chem. Soc. London 1949, 582-586.
7. Michelson, A. M.; Todd, A. R. Nucleosides, part IV: A novel synthesis of adenosine triphosphate. J. Chem. Soc. London 1949, 2487-2490.
8. Hall, H. R.; Khorana, H. G. Nucleoside polyphosphates, nucleoside polyphosphates: A synthesis of uridine-50-di- and -triphosphate. J. Am. Chem. Soc. 1954, 76, 5056-5060.
9. Potter, R. L.; Schlesinger, S.; Buettner-Janusch, V.; Thompson, L. Isolation of pyrimidine deoxyribonucleotides from the acid soluble extract of thymus. J. Biol. Chem. 1957, 226, 381-386.
10. Moffatt, J. G.; Khorana, H. G. Nucleoside polyphosphates, X: The synthesis and some reactions of nucleoside-5′-phosphomorpholidates and related compounds: Improved method for the preparation of nucleoside-5′- polyphosphates. J. Am. Chem. Soc. 1961, 83, 649-658.
11. Takaku, H.; Konishi, T.; Hatta, T. 8-Quinolyl nucleoside 5′-phosphates as a useful intermediate for the synthesis of nucleoside 5′-di- and 5′-triphosphates. Chem. Lett. 1977, 655-658.
12. Staab, H. A. Reactive N-carboxylic acid esters and N-carboxamides of imidazole and tetrazol. Ann. 1957, 609, 75-82.
13. Goldman, L.; Marsico, J. W.; Anderson, G. W. The preparation of adenosine-5′ imidazol-1-ylphosphonate and its reactions with nucleophiles: A novel synthesis of nucleoside coenzymes. J. Am. Chem. Soc. 1960, 82, 2969-2970.
14. Kozarich, J. W.; Cinault, A. C.; Hecht, S. M. Ribonucleoside phosphate via phosphorimidazolidate intermediates: Synthesis of pseudoadenosine 5′-triphosphate. Biochemistry. 1973, 12, 4458-4463.
15. Hoard, D. E.; Ott, D. G. Conversion of mono- and oligodeoxyribonucleotides to 5′-triphosphates. J. Am. Chem. Soc. 1965, 87, 1785-1788.
16. 2+ ions with nucleoside diphosphates. Nucleic Acids Res. 1977, 4, 397-403.