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Photogenerated lectin sensors produced by thiol-ene/yne photo-click chemistry in aqueous solution
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
Department of Chemistry, University of Massachusetts.
Attana AB.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.ORCID iD: 0000-0003-1121-4007
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2012 (English)In: Biosensors & bioelectronics, ISSN 0956-5663, E-ISSN 1873-4235, Vol. 34, no 1, 51-56 p.Article in journal (Refereed) Published
Abstract [en]

The photoinitiated radical reactions between thiols and alkenes/alkynes (thiol-ene and thiol-yne chemistry) have been applied to a functionalization methodology to produce carbohydrate-presenting surfaces for analyses of biomolecular interactions. Polymer-coated quartz surfaces were functionalized with alkenes or alkynes in a straightforward photochemical procedure utilizing perfluorophenylazide (PFPA) chemistry. The alkene/alkyne surfaces were subsequently allowed to react with carbohydrate thiols in water under UV-irradiation. The reaction can be carried out in a drop of water directly on the surface without photoinitiator, and any disulfide side products were easily washed away after the functionalization process. The resulting carbohydrate-presenting surfaces were evaluated in real-time studies of protein-carbohydrate interactions using a quartz crystal microbalance (QCM) flow-through system with recurring injections of selected lectins, with intermediate regeneration steps using low pH buffer. The resulting methodology proved fast, efficient and scalable to high-throughput analysis formats, and the produced surfaces showed significant protein binding with expected selectivities of the lectins used in the study.

Place, publisher, year, edition, pages
2012. Vol. 34, no 1, 51-56 p.
Keyword [en]
Photochemistry, Click chemistry, Thiol-ene/-yne, Carbohydrates, Lectins, Quartz crystal microbalance
National Category
Analytical Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-90846DOI: 10.1016/j.bios.2012.01.001ISI: 000302886500007Scopus ID: 2-s2.0-84858216975OAI: oai:DiVA.org:kth-90846DiVA: diva2:507542
Funder
Swedish Research Council, 621-2007-4709
Note
QC 20120525Available from: 2012-03-05 Created: 2012-03-01 Last updated: 2017-12-07Bibliographically approved
In thesis
1. Photochemical Ligation Techniques for Carbohydrate Biosensors and Protein Interaction Studies
Open this publication in new window or tab >>Photochemical Ligation Techniques for Carbohydrate Biosensors and Protein Interaction Studies
2012 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis concerns the development of surface ligation techniques for the preparation of carbohydrate biosensors. Several methodologies were developed based on efficient photochemical insertion reactions which quickly functionalize polymeric materials, with either carbohydrates or functional groups such as alkynes or alkenes. The alkyne/alkene surfaces were then treated with carbohydrate azides or thiols and reacted under chemoselective Cu-catalyzed azide-alkyne cycloaddition (CuAAC) or photo-radical thiol-ene/yne click chemistry, thus creating a range of carbohydrate biosensor surfaces under ambient conditions. The methodologies were evaluated by quartz crystal microbalance (QCM) and surface plasmon resonance (SPR) flow through instrumentations with recurring injections of a range of lectins, allowing for real-time analysis of the surface interactions. The developed methods were proven robust and versatile, and the generated carbohydrate biosensors showed high specificities and good capacities for lectin binding.  The methods were then used to investigate how varying the glycan linker length and/or a sulfur-linkage affect the subsequent protein binding. The survey was further explored by investigating the impact of sulfur in glycosidic linkages on protein binding, through competition assays with various O/S-linked disaccharides in solution interactions with lectins.

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2012. xi, 89 p.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2012:10
Keyword
Carbohydrates, Biosensors, CuAAC, Photochemistry, Thiol-ene/yne, Perfluorophenylazide (PFPA), Lectins, Molecular recognition, Quartz crystal microbalance (QCM), Surface plasmon resonance (SPR)
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-90956 (URN)978-91-7501-271-1 (ISBN)
Public defence
2012-03-30, F3, Lindstedtsvägen 26, Stockholm, 10:00 (English)
Opponent
Supervisors
Note
QC 20120309Available from: 2012-03-09 Created: 2012-03-05 Last updated: 2012-03-09Bibliographically approved

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