title: Selective biocatalytic acylation studies on 5'-O-(4,4'-dimethoxytrityl)-2',3'-secouridine: an efficient synthesis of UNA monomer.
abstract: Lipozyme(®) TL IM (Theremomyces lanuginosus lipase immobilized on silica) in toluene catalyzes the acylation of the 2'-OH over the 3'-OH group in 5'-O-(4,4'-dimethoxytrityl)-2',3'-secouridine (5'-O-DMT-2',3'-secouridine) in a highly selective fashion in moderate to almost quantitative yields. The turn over during benzoyl transfer reactions mediated by vinyl benzoate or benzoic anhydride was faster than in acyl transfer reactions with vinyl acetate or C(1) to C(5) acid anhydrides; except in the case of butanoic anhydride. The 2'-O-benzoyl-5'-O-DMT-2',3'-secouridine obtained by Lipozyme(®) TL IM catalyzed benzoylation of 5'-O-DMT-2',3'-secouridine was successfully converted into its 3'-O-phosphoramidite derivative in satisfactory yield, which is a building block for the preparation of oligonucleotides containing the uracil monomer of UNA (unlocked nucleic acid).
authors.affiliation: Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi, India.
authors.forename: Sunil K
authors.initials: SK
authors.lastname: Singh
authors.forename: L Chandrashekhar
authors.initials: LC
authors.lastname: Reddy
authors.forename: Smriti
authors.initials: S
authors.lastname: Srivastava
authors.forename: Carl E
authors.initials: CE
authors.lastname: Olsen
authors.forename: Yogesh S
authors.initials: YS
authors.lastname: Sanghvi
authors.forename: Niels
authors.initials: N
authors.lastname: Langkjær
authors.forename: Jesper
authors.initials: J
authors.lastname: Wengel
authors.forename: Virinder S
authors.initials: VS
authors.lastname: Parmar
authors.forename: Ashok K
authors.initials: AK
authors.lastname: Prasad
mesh_terms: D000215:Acylation; D055162:Biocatalysis; D008049:Lipase / Q000378:metabolism*; D009690:Nucleic Acid Conformation; D009696:Nucleic Acids / Q000096:biosynthesis* / Q000737:chemistry; D014320:Triphenylmethyl Compounds / Q000737:chemistry / Q000378:metabolism*; D014529:Uridine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism
chemical_list: D009696:Nucleic Acids; D014320:Triphenylmethyl Compounds; C093666:Lipozyme; D008049:Lipase; D014529:Uridine