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Exhaustive glycosylation, pegylation, and glutathionylation of a [G4]‐ene_(48) dendrimer via photoinduced thiol‐ene coupling

Lo Conte, Mauro and Robb, Maxwell J. and Hed, Yvonne and Marra, Alberto and Malkoch, Michael and Hawker, Craig J. and Dondoni, Alessandro (2011) Exhaustive glycosylation, pegylation, and glutathionylation of a [G4]‐ene_(48) dendrimer via photoinduced thiol‐ene coupling. Journal of Polymer Science Part A: Polymer Chemistry, 49 (20). pp. 4468-4475. ISSN 0887-624X. PMCID PMC3181107. https://resolver.caltech.edu/CaltechAUTHORS:20180606-110403161

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1002/pola.24888DOIArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3181107/PubMed CentralArticle
ORCID:
AuthorORCID
Robb, Maxwell J.0000-0002-0528-9857
Alternate Title:Exhaustive glycosylation, pegylation, and glutathionylation of a [G4]‐ene48 dendrimer via photoinduced thiol‐ene coupling
Additional Information:© 2011 Wiley. Received 13 June 2011; accepted 8 July 2011; published online 3 August 2011. This material is based on the work supported by federal funds from the National Heart, Lung, and Blood Institute, National Institutes of Health, Department of Health and Human Services, under Contract No. HHSN268201000043C and made use of the MRL Central Facilities supported by the MRSEC Program of the National Science Foundation (DMR 05‐20415). The Swedish research council (VR) is acknowledged for financial support under grants 2006‐3617 (M.M) and 2009‐3259 (Y.H). We thank the University of Ferrara for financial support, Dr. Angela Chambery (II Università di Napoli, Italy) for HRMS of compounds 2d and 9, and Salvatore Pacifico for help in synthetic experiments.
Funders:
Funding AgencyGrant Number
NIHHHSN268201000043C
NSFDMR 05‐20415
Swedish Research Council2006‐3617
Swedish Research Council2009‐3259
University of FerraraUNSPECIFIED
Subject Keywords:carbohydrates; click chemistry; dendrimers; irradiation; MALDI
Issue or Number:20
PubMed Central ID:PMC3181107
Record Number:CaltechAUTHORS:20180606-110403161
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20180606-110403161
Official Citation:Conte, M. L., Robb, M. J., Hed, Y. , Marra, A. , Malkoch, M. , Hawker, C. J. and Dondoni, A. (2011), Exhaustive glycosylation, pegylation, and glutathionylation of a [G4]‐ene48 dendrimer via photoinduced thiol‐ene coupling. J. Polym. Sci. A Polym. Chem., 49: 4468-4475. doi:10.1002/pola.24888
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:86838
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:06 Jun 2018 18:10
Last Modified:03 Oct 2019 19:49

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