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:

URL	URL Type	Description
http://dx.doi.org/10.1021/jo030203g	DOI	Article
http://pubs.acs.org/doi/abs/10.1021/jo030203g	Publisher	Article
http://pubs.acs.org/doi/suppl/10.1021/jo030203g	Publisher	Supporting Information

ORCID:

Author	ORCID
Stoddart, J. Fraser	0000-0003-3161-3697

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 Agency	Grant Number
UCLA	UNSPECIFIED
TSRI	UNSPECIFIED
NSF	CHE-9974928
NSF	CHE-0092036
NSF	CHE-9808175
NIH	GM60938
NIH	46462
Swedish Institute	UNSPECIFIED
Wellcome Trust	UNSPECIFIED

Issue or Number:

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

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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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