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Synthesis and Binding Affinity Analysis of α1-2- and α1-6-O/S-linked Dimannosides for the Elucidation of Sulfur in Glycosidic Bonds using Quartz Crystal Microbalance Sensors
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.
Attana AB.
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(English)Article in journal (Other academic) Submitted
Abstract [en]

Synthetic routes towards α1-2- and α1-6-linked dimannosides with S- or O-glycosidic bonds are presented. A glycosylation method was developed in which a sulfhydryl glycosyl acceptor was coupled to a 1-O-acetyl-glycosyl donor under Lewis acid catalysis. Final debenzylation of the S-linked dimannosides were accomplished through Birch reduction in high yields. The protein recognition properties of the synthesized dimannosides were then evaluated in a competition binding assay with the model lectin Con A, to investigate the effect of sulfur in the glycosidic bonds. Mannose-presenting surfaces were produced according to a previously reported Photo-Click immobilization method and the subsequent binding study was performed in an automated QCM flow through instrumentation. The recorded EC50-values correlated well to previously reported binding affinities for the O-linked dimannosides. Results were in agreement with known binding affinities, where the S-analogs displayed slightly weaker binding and a positive apparent cooperativity.

National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-90848OAI: oai:DiVA.org:kth-90848DiVA: diva2:507541
Note
QS 2012 QS 20120328Available from: 2012-03-05 Created: 2012-03-01 Last updated: 2012-03-28Bibliographically 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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