Journal
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY
Volume 49, Issue 20, Pages 4468-4475Publisher
WILEY
DOI: 10.1002/pola.24888
Keywords
carbohydrates; click chemistry; dendrimers; irradiation; MALDI
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Funding
- National Heart, Lung, and Blood Institute, National Institutes of Health, Department of Health and Human Services [HHSN268201000043C]
- MRSEC of the National Science Foundation [DMR 05-20415]
- Swedish research council (VR) [2006-3617, 2009-3259]
- University of Ferrara
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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]-ene(48) on irradiation at lambda(max) 365 nm. In all cases, the H-1 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. (C) 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 49: 4468-4475, 2011
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