title: Exhaustive glycosylation, PEGylation, and glutathionylation of a [G4]-ene(48) dendrimer via photoinduced thiol-ene coupling.
abstract: We report in this paper the use of free-radical thiol-ene coupling (TEC) for the introduction of carbohydrate, poly(ethylene glycol), and peptide fragments at the periphery of an alkene functional dendrimer. Four different sugar thiols including glucose, mannose, lactose and sialic acid, two PEGylated thiols and the natural tripeptide glutathione were reacted with a fourth generation alkene functional dendrimer [G4]-ene(48) upon irradiation at λ(max) 365 nm. In all cases, the (1)H NMR spectra of the crude reaction mixture revealed the complete disappearance of alkene proton signals indicating the quantitative conversion of all 48 alkene groups of the dendrimer. With one exception only, all dendrimer conjugates were isolated in high yields (70-94%), validating the high efficiency of multiple TEC reactions on a single substrate. All isolated and purified compounds were analyzed by MALDI-TOF spectrometry and gave spectra consistent with the assigned structure.
authors.affiliation: Dipartimento di Chimica, Laboratorio di Chimica Organica, Università di Ferrara, Via L. Borsari 46, 44100 Ferrara, Italy.
authors.forename: Mauro
authors.initials: M
authors.lastname: Lo Conte
authors.forename: Maxwell J
authors.initials: MJ
authors.lastname: Robb
authors.forename: Yvonne
authors.initials: Y
authors.lastname: Hed
authors.forename: Alberto
authors.initials: A
authors.lastname: Marra
authors.forename: Michael
authors.initials: M
authors.lastname: Malkoch
authors.forename: Craig J
authors.initials: CJ
authors.lastname: Hawker
authors.forename: Alessandro
authors.initials: A
authors.lastname: Dondoni