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Photo-Click Immobilization of Carbohydrates on Polymeric Surfaces - A Quick Method to Functionalize Surfaces for Biomolecular Recognition Studies
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
2009 (English)In: Bioconjugate chemistry, ISSN 1043-1802, E-ISSN 1520-4812, Vol. 20, no 12, 2364-2370 p.Article in journal (Refereed) Published
Abstract [en]

Methods to rapidly functionalize specific polymeric surfaces with alkynes, which can subsequently be linked to azide-containing carbohydrates, are presented. The methods comprise two main concepts: azide photoligation and Cu-catalyzed azide-alkyne cycloaddition. 2-Azidoethyl-functionalized CL-D-mannopyranoside was synthesized and covalently attached to alkyne-functionalized polymeric surfaces using the techniques. The protein recognition properties of the carbollydrate-presenting surfaces were evaluated using quartz crystal microbalance biosensor instrumentation.

Place, publisher, year, edition, pages
2009. Vol. 20, no 12, 2364-2370 p.
National Category
Polymer Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-19043DOI: 10.1021/bc9003519ISI: 000272690100021PubMedID: 19888719Scopus ID: 2-s2.0-72449192287OAI: oai:DiVA.org:kth-19043DiVA: diva2:337090
Note

QC 20100525

Available from: 2010-08-05 Created: 2010-08-05 Last updated: 2016-07-21Bibliographically approved
In thesis
1. Photochemical Surface Functionalization: Synthesis, Nanochemistry and Glycobiological Studies
Open this publication in new window or tab >>Photochemical Surface Functionalization: Synthesis, Nanochemistry and Glycobiological Studies
2011 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis mainly deals with the development of photochemical approaches to immobilize carbohydrates on surfaces for glycobiological studies. These approaches have been incorporated into a number of state-of-the-art nanobio-platforms, including carbohydrate microarrays, surface plasmon resonance (SPR), quartz crystal microbalance (QCM), atomic force microscopy (AFM), and glyconanomaterials. All the surfaces have displayed good binding capabilities and selectivities after functionalization with carbohydrates, and a range of important data have been obtained concerning surface characteristics and carbohydrate-protein interactions, based on the platforms established. Besides, a variety of non-carbohydrate and carbohydrate-based molecules have been synthesized, during which process the mutarotation of 1-glycosyl thiols and the stereocontrol in 1-S-glycosylation reactions have been thoroughly studied.

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2011. 86 p.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2011:47
Keyword
Carbohydrates, Glycobiology, Carbohydrate-protein interactions, Perfluorophenylazide (PFPA), Photochemistry, Carbohydrate surface immobilization, Carbohydrate microarrays, Surface plasmon resonance (SPR), Quartz crystal microbalance (QCM), Atomic force microscopy (AFM), Glyconanomaterials, Concanavalin A (Con A), Cyanovirin-N (CV-N), 1-Glycosyl thiols; Mutarotation, 1-S-glycosylation, Stereocontrol
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-41973 (URN)978-91-7501-072-4 (ISBN)
Public defence
2011-10-21, F3, Lindstedtsvägen 26, KTH, Stockholm, 13:00 (English)
Opponent
Supervisors
Note
QC 20111004Available from: 2011-10-04 Created: 2011-10-04 Last updated: 2011-10-04Bibliographically approved
2. 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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