Exhaustive glycosylation, pegylation, and glutathionylation of a [G4]-ene48 dendrimer via photoinduced thiol-ene coupling

Authors

  • Mauro Lo Conte,

    1. Dipartimento di Chimica, Laboratorio di Chimica Organica, Università di Ferrara, Via L. Borsari 46, 44100 Ferrara, Italy
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  • Maxwell J. Robb,

    1. Department of Chemistry and Biochemistry, Materials Department, and Materials Research Laboratory (MRL), University of California, Santa Barbara, California 93106
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  • Yvonne Hed,

    1. The Royal Institute of Technology, School of Chemical Science and Engineering, Division of Coating Technology, Teknikringen 56-58, SE-10044 Stockholm, Sweden
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  • Alberto Marra,

    1. Dipartimento di Chimica, Laboratorio di Chimica Organica, Università di Ferrara, Via L. Borsari 46, 44100 Ferrara, Italy
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  • Michael Malkoch,

    1. The Royal Institute of Technology, School of Chemical Science and Engineering, Division of Coating Technology, Teknikringen 56-58, SE-10044 Stockholm, Sweden
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  • Craig J. Hawker,

    Corresponding author
    1. Department of Chemistry and Biochemistry, Materials Department, and Materials Research Laboratory (MRL), University of California, Santa Barbara, California 93106
    • Department of Chemistry and Biochemistry, Materials Department, and Materials Research Laboratory (MRL), University of California, Santa Barbara, California 93106
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  • Alessandro Dondoni

    1. Dipartimento di Chimica, Laboratorio di Chimica Organica, Università di Ferrara, Via L. Borsari 46, 44100 Ferrara, Italy
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Abstract

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 has been reported in this article. 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]-ene48 on irradiation at λmax 365 nm. In all cases, the 1H 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 matrix assisted laser desorption ionization-time of flight (MALDI-TOF) spectrometry and gave spectra consistent with the assigned structure. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011

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