title: Chemoenzymatic convergent synthesis of 2'-O,4'-C-methyleneribonucleosides.
abstract: Novozyme-435-catalyzed efficient regioselective acetylation of one of the two diastereotopic hydroxymethyl functions in 3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-d-ribofuranose has been achieved. The enzymatic methodology has been successfully utilized for convergent synthesis of bicyclic nucleosides (LNA monomers) T, U, A, and C. Further, it has been demonstrated that Novozyme-435 can be used for 10 cycles of the acylation reaction without losing selectivity and efficiency.
authors.affiliation: Bioorganic Laboratory, Department of Chemistry, University of Delhi , Delhi 110 007, India.
authors.forename: Vivek K
authors.initials: VK
authors.lastname: Sharma
authors.forename: Manish
authors.initials: M
authors.lastname: Kumar
authors.forename: Carl E
authors.initials: CE
authors.lastname: Olsen
authors.forename: Ashok K
authors.initials: AK
authors.lastname: Prasad
mesh_terms: D000215:Acylation; D055162:Biocatalysis; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D008049:Lipase / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D012263:Ribonucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C000593338:3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-alpha-D-ribofuranose; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D009005:Monosaccharides; D009705:Nucleosides; D012263:Ribonucleosides; C093667:Novozyme 435; D008049:Lipase