title: An expedient biocatalytic procedure for abasic site precursors useful in oligonucleotide synthesis.
abstract: Preparation of abasic site precursors through a divergent chemoenzymatic synthesis has been accomplished. Several biocatalysts and acylating agents were studied furnishing a practical and scalable green method useful for industrial applications. Highly regioselective acylation and deacylation reactions with 1,2-dideoxy-D-ribose are described resulting in excellent yield. A fast, atom-efficient and convenient synthesis of 3-, and 5-O-DMTr-1,2-dideoxyribose 17 and 19 has been achieved. These compounds are useful precursors for the preparation of phosphoramidites required for the assembly of oligonucleotides containing the tetrahydrofuran abasic lesions.
authors: Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Biotecnología de Asturias, Universidad de Oviedo, 33006, Oviedo, Asturias, Spain.
authors: Saúl
authors: S
authors: Martínez-Montero
authors: Susana
authors: S
authors: Fernández
authors: Yogesh S
authors: YS
authors: Sanghvi
authors: Vicente
authors: V
authors: Gotor
authors: Miguel
authors: M
authors: Ferrero
mesh_terms: D000215:Acylation; D055162:Biocatalysis; D002861:Chromobacterium / Q000201:enzymology; D003855:Deoxyribose / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D055772:Green Chemistry Technology / Q000379:methods*; D008049:Lipase / Q000378:metabolism; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000378:metabolism; D011549:Pseudomonas / Q000201:enzymology
chemical_list: D009841:Oligonucleotides; D003855:Deoxyribose; C071180:1,2-dideoxyribose; D008049:Lipase