Synthesis and biological evaluation of 9-N-oxamyl sialosides as Siglec-7 ligands

Horst Prescher; Stephan Gütgemann; Martin Frank; Elena Kuhfeldt; Carsten Watzl; Reinhard Brossmer

doi:10.1016/j.bmc.2015.06.069

Synthesis and biological evaluation of 9-N-oxamyl sialosides as Siglec-7 ligands

Bioorg Med Chem. 2015 Sep 1;23(17):5915-21. doi: 10.1016/j.bmc.2015.06.069. Epub 2015 Jul 7.

Authors

Horst Prescher¹, Stephan Gütgemann², Martin Frank³, Elena Kuhfeldt¹, Carsten Watzl², Reinhard Brossmer⁴

Affiliations

¹ G3-BioTec, 69207 Sandhausen, Germany.
² Institute of Immunology, University of Heidelberg, 69120 Heidelberg, Germany.
³ Molecular Structure Analysis Core Facility-W160, German Cancer Research Center, 69120 Heidelberg, Germany.
⁴ G3-BioTec, 69207 Sandhausen, Germany; Biochemistry Center, University of Heidelberg, 69120 Heidelberg, Germany. Electronic address: reinhard.brossmer@bzh.uni-heidelberg.de.

PMID: 26234906
DOI: 10.1016/j.bmc.2015.06.069

Abstract

Siglecs (sialic acid recognizing immunoglobulin like lectins) are a family of lectins with specificity for sialic acid containing carbohydrates. Synthetic sialic acid derivatives with high affinity proved useful to unravel the biological role of the ligand binding domain, although many of their functions in immunity remain unknown. Here we present design, synthesis, affinity evaluation and molecular modeling of novel 9-N-oxamoyl modified sialosides as Siglec-7 ligands.

Keywords: Lectin; Neuraminic acid; Sialic acid; Sialoside; Siglec.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Lectins / metabolism
Ligands
Molecular Structure
N-Acetylneuraminic Acid / chemistry*
Neuraminic Acids / chemistry*

Substances

Lectins
Ligands
Neuraminic Acids
N-Acetylneuraminic Acid