Chemoselective deprotection of α-indole and imidazole ribonucleosides

Nucleosides, Nucleotides and Nucleic Acids

Volumn 26, Issue 1, 2007, Pages 1-8

  Chandra, Tilak ^a   Brown, Kenneth L ^a  

^a OHIO UNIVERSITY   (United States)

Author keywords

Biosynthesis; Chemoselective; Coenzyme B12; Glycosylation

Indexed keywords

ACID; BENZIMIDAZOLE DERIVATIVE; ETHER; FORMIC ACID; IMIDAZOLE DERIVATIVE; INDOLE DERIVATIVE; RIBONUCLEOSIDE DERIVATIVE;

ANALYTIC METHOD; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DEPROTECTION REACTION; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; ROOM TEMPERATURE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

FORMIC ACIDS; IMIDAZOLES; INDOLES; MAGNETIC RESONANCE SPECTROSCOPY; RIBONUCLEOSIDES; TEMPERATURE;

EID: 33845669369     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770601052216     Document Type: Article

References (24)

1. 12-dependent ribonucleotide reductase from Lactobacillus Leichmannii. J. Am. Chem. Soc. 1998, 120, 9466-9474.
2. 12. Chem. Rev. 2005, 105(6), 2075-2149. Washington, DC, United States.
3. 12. Dalton Trans. 2006, 9, 1123-1133.
4. 12 analog with an imidazole axial nucleoside. Dalton Trans. 2005,(4), 782-787.
5. 12 derivatives with altered axial nucleotides: Probing the mechanochemical triggering hypothesis in ribonucleotide reductase. Inorg. Chem. 2001, 40, 5942-5947.
6. 12 with an α-adenosyl upper axial ligand. Biochemistry 1998, 37, 9704-9715.
7. 12, Methods in Enzymology 1971, 18 C, 82//;92.
8. 12. J. Chem. Soc. [section C organic] 1969, 8, 1163-1166.
9. 12. Helv. Chim. Acta. 1960, 43, 704-712.
10. Hay, B.P.; Finke, R.G. Thermolysis of the cobalt-carbon bond of adenosylcobalamin. 2. Products, kinetics, and cobalt-carbon bond dissociation energy in aqueous solution. J. Am. Chem. Soc. 1986, 108, 4820-4829.
11. Hay, B.P.; Finke, R.G. Thermolysis of the cobalt-carbon bond in adenosylcorrins. 3. Quantification of the axial base effect in adenosylcobalamin by the synthesis and shermolysis of axial base-free adenosylcobinamide. insights into the energetics of enzyme-assisted cobalt-carbon bond homolysis. J. Am. Chem. Soc. 1987, 109, 8012-8018.
12. Stevens, J.D.; Ness, R.K.; Fletcher, H.G., Jr.; Hewitt, G., Jr. Syntheses with partially benzylated sugars. XI. Studies on the synthesis of the anomeric 5,6-dimethyl-1-D-ribofuranosylbenzimidazoles ribazoles. Comparison of the condensation of 2, 3, 5-tri-O)-benzoyl-D-ribofuranosyl bromide and 2,3,5-tri-O-benzyl-D-ribofuranosyl chloride with 5,6-dimethylbenzimidazole. J. Org. Chem. 1968, 33(5), 1806-1810.
13. 12. XIX. Synthesis of the 1-D-ribosides of 5, 6-dimethylbenzimidazole. J. Am. Chem. Soc. 1952, 74, 4521-4525.
14. Chandra, T.; Zou, S.; Brown, K.L. Low temperature dehydrogenation of α-indoline nucleosides. Tetrahedron Lett. 2004, 45, 7783-7786.
15. Chandra, T.; Brown, K.L. Direct glycosylation: Synthesis of α-indoline ribonucleosides. Tetrahedron Lett. 2005, 46(12), 2071-2074.
16. Brown, K.L.; Chandra, T.; Zou, S.; Valente, E. Regioselective glycosylation: synthesis of α-indoline nucleosides. Nucleosides, Nucleotides and Nucleic Acids 2005, 24(8), 1147-1165.
17. Chandra, T.; Brown, K.L. Deprotection of α-imidazole/benzimidazole ribonucleosides by catalytic carbon tetrabromide initiated photolysis. Tetrahedron Lett. 2005, 46(49), 8617-8619.
18. Chandra, T.; Zou, S.; Valente, E.J.; Brown, K.L. Regio- and stereo-selective glycosylation: Synthesis of 5-haloimidazole α-ribonucleosides. J. Org. Chem. 2006, 71(31), 5000-5003.
19. 2′ dipolar relaxation mechanisms in ribonucleosides: Application to characterize their anomeric configuration. J. Phys. Chem. B. 2006, 106, 5-8.
20. Greene, T.W.; Wuts, P.G.M. Protective Groups in Organic Synthesis. 3rd edn., Wiley, New York, 1999.
21. Bessodes, M.; Komiotis, D. Antonakis K. Rapid and selective detritylation of primary alcohols using formic acid. Tetrahedron Lett. 1986, 27, 579-582.
22. MacCoss, M.; Cameron, D.J. Facile detritylation of nucleoside derivatives by using trifluoroacetic acid. Carbohydr. Res. 1978, 60, 206-209.
23. Mukaiyama, T.; Hashimoto, Y.; Hayashi, Y.; Shoda, S-i. Stereoselective synthesis of α-ribonucleosides from 1-hydroxy sugars by using 2-fluoropyridinium tosylate. Chem. Lett. 1984,, 57-560.
24. Chen, J.J.; Wei, Y.; Drach, J.C.; Townsend, L.B. Synthesis and antiviral evaluation of trisubstituted indole N-nucleosides as analogues of 2,5,6-trichloro-1-(b-D-ribofuranosyl)benzimidazole (TCRB). J. Med. Chem. 2000, 43, 2449-2456.