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Chemically Defined Sialoside Scaffolds for Investigation of Multivalent Interactions with Sialic Acid Binding Proteins

Kalovidouris, Stacey A. and Blixt, Ola and Nelson, Alshakim and Vidal, Sébastien and Turnbull, W. Bruce and Paulson, James C. and Stoddart, J. Fraser (2003) Chemically Defined Sialoside Scaffolds for Investigation of Multivalent Interactions with Sialic Acid Binding Proteins. Journal of Organic Chemistry, 68 (22). pp. 8485-8493. ISSN 0022-3263. doi:10.1021/jo030203g. https://resolver.caltech.edu/CaltechAUTHORS:20170411-132637114

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Abstract

Four glycodendrons and a glycocluster were synthesized from carbohydrate building blocks to form paucivalent (di- to tetravalent) structures of controlled scaffold architectures. Enzymatic sialylation of the functionalized cluster and dendrons, terminated in lactose residues, generated a library of paucivalent synthetic sialosides displaying sialic acids with different dispositions. These newly constructed bioactive sialic acid-based structures were differentially recognized by sialoadhesin, a mammalian macrophage sialic acid binding protein. The binding of the sialosides to sialoadhesin was evaluated by an enzyme-linked immunosorbant assay to investigate the complementarity of scaffold structure and binding to sialoadhesin. Modulating the interaction between sialoadhesin and its sialic acid ligands has important implications in immunobiology.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/jo030203gDOIArticle
http://pubs.acs.org/doi/abs/10.1021/jo030203gPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/jo030203gPublisherSupporting Information
ORCID:
AuthorORCID
Stoddart, J. Fraser0000-0003-3161-3697
Additional Information:© 2003 American Chemical Society. Received June 20, 2003. Publication Date (Web): October 9, 2003. We thank UCLA and TSRI for generous financial assistance. The material based upon the use of the Brüker Avance 500 NMR and ZAB-SE mass spectrometers was supported by the National Science Foundation under equipment grant numbers CHE-9974928, CHE-0092036, and CHE-9808175. This work was also funded in part by the grants from NIGMS (GM60938) and the NCI (46462). The Swedish Institute is acknowledged for financial support to O.B., and The Wellcome Trust, for the award of an International Prize Travelling Research Fellowship to W.B.T.
Funders:
Funding AgencyGrant Number
UCLAUNSPECIFIED
TSRIUNSPECIFIED
NSFCHE-9974928
NSFCHE-0092036
NSFCHE-9808175
NIHGM60938
NIH46462
Swedish InstituteUNSPECIFIED
Wellcome TrustUNSPECIFIED
Issue or Number:22
DOI:10.1021/jo030203g
Record Number:CaltechAUTHORS:20170411-132637114
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170411-132637114
Official Citation:Chemically Defined Sialoside Scaffolds for Investigation of Multivalent Interactions with Sialic Acid Binding Proteins Stacey A. Kalovidouris, Ola Blixt, Alshakim Nelson, Sébastien Vidal, W. Bruce Turnbull, James C. Paulson, and J. Fraser Stoddart The Journal of Organic Chemistry 2003 68 (22), 8485-8493 DOI: 10.1021/jo030203g
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76517
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:11 Apr 2017 20:54
Last Modified:15 Nov 2021 17:00

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