Chen, Gaojian, Tao, Lei, Mantovani, Giuseppe, Geng, J., Nystrom, Daniel and Haddleton, David M. (2007) A modular click approach to glycosylated polymeric beads : Design, synthesis and preliminary lectin, recognition studies. Macromolecules, Vol.40 (No.21). pp. 7513-7520. doi:10.1021/ma071362v ISSN 0024-9297 .

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Abstract

Covalent immobilization of a range of carbohydrate derivatives onto polymeric resin beads is described. Copper-catalyzed Huisgen [2 + 3] cycloaddition (often termed click chemistry) was used to graft mannose-containing azides to complementarily functionalized alkyne surfaces, namely (a) Wang resin or (b) Rasta particles consisting of a clickable alkyne polymer loose outer shell and a Wang resin inner core. For the second approach, Wang resin beads were first converted into immobilized living radical polymerization initiators with subsequent polymerization of trimethylsilanyl-protected propargyl methacrylate followed by deprotection with TBAF to yield the desired polyalkyne clickable scaffold. The appropriate (x-mannopyranoside azide was then clicked onto the bead to give a mannose functionalized Rasta resin. IR, gel-phase H-1 NMR, and elemental analysis have been used to characterize the modified resins. The binding abilities of these D-mannose-modified particles were subsequently tested using fluorescein-labeled Concanavalin A (Con A), a lectin that binds certain mannose-containing molecules. Preliminary results indicated that the novel glyco-hybrid materials presented in this work are able to efficiently recognize mannose-binding model lectins such as Con A, opening the way for their potential application in affinity chromatography, sensors, and other protein recognition/separation fields.

Item Type:	Journal Article
Subjects:	Q Science > QD Chemistry
Divisions:	Faculty of Science, Engineering and Medicine > Science > Chemistry
Journal or Publication Title:	Macromolecules
Publisher:	American Chemical Society
ISSN:	0024-9297
Official Date:	16 October 2007
Dates:	Date Event 16 October 2007 Published
Volume:	Vol.40
Number:	No.21
Number of Pages:	8
Page Range:	pp. 7513-7520
DOI:	10.1021/ma071362v
Status:	Peer Reviewed
Publication Status:	Published
Access rights to Published version:	Restricted or Subscription Access

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