Literature DB >> 16270659

Regioselective glycosylation: synthesis of alpha-indoline nucleosides.

Kenneth L Brown1, Tilak Chandra, Shawn Zou, Edward J Valente.   

Abstract

Novel indoline ribonucleosides with the alpha-N-glycoside configuration are synthesized with very high regioselectivity in 90-96%yield, using TMS protected indolines and 2,3-O-(1-methylethylidene)-5-O-(triphenylmethyl)-alpha/beta-D-ribofuranose. The structures of these ribonucleosides were elucidated with X-ray crystallography as well as 2D (NOESY, COSY, and HMQC) NMR spectroscopy.

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Year:  2005        PMID： 16270659      PMCID： PMC1383618          DOI： 10.1081/NCN-200067398

Source DB:  PubMed          Journal:  Nucleosides Nucleotides Nucleic Acids        ISSN： 1525-7770            Impact factor:   1.381


  7 in total

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Authors:  M Haga; R K Ness; H G Fletcher
Journal:  J Org Chem       Date:  1968-05       Impact factor: 4.354

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5.  Enzymatic activity of coenzyme B(12) derivatives with altered axial nucleotides: probing the mechanochemical triggering hypothesis in ribonucleotide reductase.

Authors:  K L Brown; X Zou; J Li; G Chen
Journal:  Inorg Chem       Date:  2001-11-05       Impact factor: 5.165

6.  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.

Authors:  Cheom-Gil Cheong; Jorge C Escalante-Semerena; Ivan Rayment
Journal:  J Biol Chem       Date:  2002-07-05       Impact factor: 5.157

7.  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.

Authors:  J D Stevens; R K Ness; H G Fletcher
Journal:  J Org Chem       Date:  1968-05       Impact factor: 4.354
  7 in total
  1 in total

1.  Vitamin B(12) and alpha-Ribonucleosides.

Authors:  Tilak Chandra; Kenneth L Brown
Journal:  Tetrahedron       Date:  2008-01-01       Impact factor: 2.457
  1 in total

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