title: Sugar-oligoamides: synthesis of DNA minor groove binders.
abstract: Sugar-oligoamides have been designed and synthesized as structurally simple carbohydrate-based ligands to study carbohydrate-minor groove DNA interactions. Here we report an efficient solution-phase synthetic strategy to obtain two broad families of sugar-oligoamides. The first type, structure vector A (-Py[Me]-γ-Py-Ind), has a methyl group present as a substituent on the nitrogen of pyrrole B, connected to the C terminal of the oligoamide fragment. The second type, structure vector B (-Py[(CH(2))(11)OH]-γ-Py-Ind), has an alkyl chain present on the nitrogen of pyrrole B connected to the C terminal of the oligoamide fragment and has been designed to access to di- and multivalent sugar-oligoamides. By using sequential DIPC/HOBt coupling reactions, the oligoamide fragment -Py[R]-γ-Py-Ind has been constructed. The last coupling reaction between the anomeric amino sugar and the oligoamide fragment was carried out by activating the acid derivative as a BtO- ester, which has been performed by using TFFH. The isolated esters (BtO-Py[R]-γ-Py-Ind) were coupled with selected amino sugars using DIEA in DMF. The synthesis of two different selective model vectors (vector A (1) and vector B (2)) and two types of water-soluble sugar-oligoamide ligands, with vector A structure (compounds 3-7) and with vector B structure (compound 8), was carried out.
authors.affiliation: Departamento de Síntesis, Estructura y Propiedades de los Compuestos Orgánicos, Instituto de Química Orgánica General, CSIC, c/Juan de la Cierva 3, 28006 Madrid, Spain.
authors.forename: Concepción
authors.initials: C
authors.lastname: Badía
authors.forename: Florence
authors.initials: F
authors.lastname: Souard
authors.forename: Cristina
authors.initials: C
authors.lastname: Vicent
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry*; D000595:Amino Acid Sequence; D002241:Carbohydrates / Q000138:chemical synthesis / Q000737:chemistry; D004247:DNA / Q000737:chemistry*; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011758:Pyrroles / Q000737:chemistry*
chemical_list: D000577:Amides; D002241:Carbohydrates; D008024:Ligands; D011758:Pyrroles; D004247:DNA