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Terminal-end functionalization of chondroitin sulfate for the synthesis of biomimetic proteoglycans
Journal article   Peer reviewed

Terminal-end functionalization of chondroitin sulfate for the synthesis of biomimetic proteoglycans

S. Sarkar, S.E. Lightfoot-Vidal, C.L. Schauer, E. Vresilovic and M. Marcolongo
Carbohydrate polymers, v 90(1), pp 431-440
01 Sep 2012
PMID: 24751062

Abstract

1H NMR Biomimetic Bottle brush polymer synthesis Chondroitin sulfate Proteoglycan
► In this study we identify chondroitin sulfate (CS) with a terminal primary amine. ► A vinyl monomer was conjugated to the CS terminal amine without side reactions. ► CS was immobilized by its terminal amine to epoxy-functionalized surfaces. ► Proteoglycan mimetics may be synthesized from the amine and vinyl terminated CS. Chondroitin sulfate (CS) based bottle brush proteoglycan mimetics may be employed to restore tissue functionality. Synthesis of CS bottle brush structures requires immobilization of CS at its terminal end. In this study, we investigated commercially available natural CS for use in CS bottle brush synthesis. A terminal primary amine on CS was identified and utilized to conjugate amine-reactive vinyl monomers (i.e. acrylic acid and allyl glycidyl ether). Conjugation of vinyl monomers to the CS terminal amine was confirmed using a fluorescamine assay, 1H NMR, and ATR-FTIR. CS was also immobilized onto epoxy functionalized surfaces via the CS terminal primary amine as confirmed by contact angle measurements of surface wettability. Attachment of polymeriziable end groups to CS and attachment of CS to functionalized substrates demonstrated here are the first steps towards synthesis of CS bottle brush PG mimics.

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Collaboration types
Domestic collaboration
Web of Science research areas
Chemistry, Applied
Chemistry, Organic
Polymer Science
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