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Synthesis and binding affinity analysis of alpha 1-2-and alpha 1-6-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.
KTH, School of Chemical Science and Engineering (CHE), Chemistry.
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2017 (English)In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 452, 35-42 p.Article, review/survey (Refereed) Published
Abstract [en]

The role of sulfur in glycosidic bonds has been evaluated using quartz crystal microbalance methodology. Synthetic routes towards alpha 1-2- and alpha 1-6-linked dimannosides with S-or O-glycosidic bonds have been developed, and the recognition properties assessed in competition binding assays with the cognate lectin concanavalin A. Mannose-presenting QCM sensors were produced using photoinitiated, nitrenemediated immobilization methods, and the subsequent binding study was performed in an automated flow-through instrumentation, and correlated with data from isothermal titration calorimetry. The recorded Kd-values corresponded well with reported binding affinities for the O-linked dimannosides with affinities for the alpha 1-2-linked dimannosides in the lower micromolar range. The S-linked analogs showed slightly disparate effects, where the alpha 1-6-linked analog showed weaker affinity than the O-linked dimannoside, as well as positive apparent cooperativity, whereas the alpha 1-2-analog displayed very similar binding compared to the O-linked structure. 

Place, publisher, year, edition, pages
ELSEVIER SCI LTD , 2017. Vol. 452, 35-42 p.
Keyword [en]
Photochemistry, Thiosaccharides, CuAAC, Carbohydrates, Lectins, Biosensor, Quartz crystal microbalance
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-217933DOI: 10.1016/j.carres.2017.09.015ISI: 000414691600005PubMedID: 29054052Scopus ID: 2-s2.0-85031790039OAI: oai:DiVA.org:kth-217933DiVA: diva2:1158860
Note

QC 20171121

Available from: 2017-11-21 Created: 2017-11-21 Last updated: 2017-11-21Bibliographically approved

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Ramström, Olof

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