title: Design and divergent synthesis of aza nucleosides from a chiral imino sugar.
abstract: Several novel nucleoside analogues as potential inhibitors of glycosidases and purine nucleoside phosphorylase (PNP) have been synthesized via selective coupling of an appropriate nucleobase at different positions of an orthogonally protected imino sugar as a common precursor. This synthetic strategy offers a straightforward protocol for the assembly of imino sugar containing nucleosides, establishing a new repertoire of molecules as potential therapeutics.
authors.affiliation: Departamento de Quı́mica Orgánica e Inorgánica and Instituto Universitario de Biotecnologı́a de Asturias, Universidad de Oviedo, 33006 Oviedo (Asturias), Spain.
authors.forename: Saúl
authors.initials: S
authors.lastname: Martínez-Montero
authors.forename: Susana
authors.initials: S
authors.lastname: Fernández
authors.forename: Yogesh S
authors.initials: YS
authors.lastname: Sanghvi
authors.forename: Jyoti
authors.initials: J
authors.lastname: Chattopadhyaya
authors.forename: Muthupandian
authors.initials: M
authors.lastname: Ganesan
authors.forename: Namakkal G
authors.initials: NG
authors.lastname: Ramesh
authors.forename: Vicente
authors.initials: V
authors.lastname: Gotor
authors.forename: Miguel
authors.initials: M
authors.lastname: Ferrero
mesh_terms: D020029:Base Pairing; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors* / Q000737:chemistry / Q000378:metabolism; D006801:Humans; D050111:Imino Sugars / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D011683:Purine-Nucleoside Phosphorylase / Q000037:antagonists & inhibitors* / Q000737:chemistry / Q000378:metabolism; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C574742:(2S,3S,4R,5S)-2-(9-adenylmethyl)-(3-O,5-C-methylene)-N-(p-toluenesulfonamido)pyrrolidine; C574743:(2S,3S,4R,5S)-2-(9-adenylmethyl)-(3-O,5-C-methylene)pyrrolidine; D050111:Imino Sugars; D009705:Nucleosides; D011759:Pyrrolidines; D013449:Sulfonamides; D011683:Purine-Nucleoside Phosphorylase; D006026:Glycoside Hydrolases