Regioselective glycosylation: Synthesis of α-indoline nucleosides

Nucleosides, Nucleotides and Nucleic Acids

Volumn 24, Issue 8, 2005, Pages 1147-1165

  Brown, Kenneth L ^a   Chandra, Tilak ^a   Zou, Shawn ^a   Valente, Edward J ^b  

^a OHIO UNIVERSITY   (United States)

^b MISSISSIPPI COLLEGE   (United States)

Author keywords

Biosynthesis; Coenzyme B12; Glycosylation; Regioselective

Indexed keywords

2,3 O (1 METHYLETHYLIDENE) 5 O (TRIPHENYLMETHYL) ALPHA DEXTRO RIBOFURANOSE; 2,3 O (1 METHYLETHYLIDENE) 5 O (TRIPHENYLMETHYL) BETA DEXTRO RIBOFURANOSE; ALPHA N GLYCOSIDE; FURAN DERIVATIVE; GLYCOSIDE; RIBONUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; GLYCOSYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; NUCLEIC ACID STRUCTURE; NUCLEIC ACID SYNTHESIS; QUANTUM YIELD; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; GLYCOSYLATION; INDOLES; MOLECULAR STRUCTURE; RIBONUCLEOSIDES;

EID: 27644496020     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1081/NCN-200067398     Document Type: Article

References (21)

1. 12 derivatives with altered axial nucleotides: probing the mechanochemical triggering hypothesis in ribonucleotide reductase. Inorg. Chem. 2001, 40, 5942-5947.
2. 12: synthesis and solution spectroscopic and crystal structure analysis of coβ- cyanoimidazolylcobamide. Inorg. Chem. 1994, 33, 4128-4139.
3. Cheong, C.-G.; Escalante-Semerena, J.C.; Rayment, I. Capture of a labile substrate by expulsion of water molecules from the active site of nicotinate mononucleotide: 5,6-dimethylbenzimidazole phosphoribosyltransferase (CobT) from Salmonella enterica. J. Biol. Chem. 2002, 277, 41120-41127.
4. 12. Methods Enzymol. 1971, 18C, 82-92.
5. 12. J. Chem. Soc., Section C: Organic 1969, 8, 1163-1166.
6. Preobrazhenskaya, M.N.; Yartseva, I.V.; Ektova, L.V. 1-β-D- ribofuranosylindole. The "indoline-indole" method applied to indole nucleosides. Nucl. Acid Chem. 1978, 2, 721-723.
7. Chandra, T.; Zou, S.; Brown, K.L. Low temperature dehydrogenation of α-indoline nucleosides. Tetrahedron Lett. 2004, 45, 7783-7786.
8. Mukaiyama, T.; Hashimoto, Y.; Hayashi, Y.; Shoda, S. Stereoselective synthesis of α-ribonucleosides from 1-hydroxy sugars by using 2-fluoropyridinium tosylate. Chem. Lett. 1984, 4, 557-560.
9. Klein, R.S.; Ohrui, H.; Fox, J.J. Synthesis of 2,3-O-isopropylidene-5-O- trity1-β-D-ribofuranosyl chloride. J. Carbohydr., Nucleosides Nucleotides 1974, 1(3), 265-269.
10. Haga, M.; Ness, R.K.; Fletcher, H.G., Jr. Syntheses with partially benzylated sugars. XII. 3,5,-Di-O-benzyl-beta-D-ribofuranose and its use as an intermediate in the synthesis of partially substituted ribonucleosides. J. Org. Chem. 1968, 33, 1810-1815.
11. Stevens, J.D.; Ness, R.K.; Fletcher, H.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, 1806-1810.
12. Tyson, F.T. Indole preparation. J. Am. Chem. Soc. 1941, 63, 2024-2025.
13. Leo, M.O.; Catharine, O.W. The synthesis and the characterization of nonmethyl and dimethylindoles. Can. J. Res. 1947, 25B, 1-13.
14. Gribble, G.W.; Hoffman, J.H. Reaction of sodium borohydride in acetic media: VI. Reduction of indoles with cyanoborohydride in acetic acid. Synthesis 1977, 12, 859-860.
15. Fox, P.A.; Gray, S.D.; Bruck, M.A.; Wigley, D.E. Tetrahydroquinolinyl amido and indolinyl amido complexes of tantalum as models for substrate-catalyst adducts in hydrodenitrogenation catalysis. Inorg. Chem. 1996, 35, 6027-6036.
16. Harpp, D.N.; Steliou, K.; Chan, T.H. Synthesis and reaction of some new sulfur transfer reagents. J. Am. Chem. Soc. 1978, 100(4), 1222-1228.
17. Sundaralingam, M. Stereochemistry of nucleic acids and their constituents. XVIII. Conformational analysis of α-nucleosides by x-ray crystallography. J. Am. Chem. Soc. 1971, 93, 6644-6647.
18. Tapiero, C.; Imbach, J.L.; Townsend, L.B.; Tipson, R.S. The determination of anomeric configuration of D-ribofuranosyl nucleoside by proton magnetic resonance spectroscopy. Nucl. Acid Chem. 1978, 2, 1055-1059.
19. Imbach, J.L.; Barascut, J.L.; Kam, B.L.; Rayner, B.; Tamby, C.; Tapiero, C. Synthesis of nucleosides. III. New criterion determination of the anomer configuration of ribosidic nucleosides. J. Heterocycl. Chem. 1973, 10(6), 1069-1070.
20. Rayner, B.; Tapiero, C.; Imbach, J.L. Studies on the Δδ criterion for determining the anomeric configuration of ribofuranosyl nucleosides. Carbohydr. Res. 1976, 47(2), 195-202.
21. Cousineau, T.J.; Secrist, J.A., III. Synthesis of certain β-D-ribofuranosylthiazole C-nucleosides from a versatile precursor. J. Org. Chem. 1979, 44, 4351-4358.