Epimers Switch Galectin-9 Domain Selectivity: 3 N-Aryl Galactosides Bind the C-Terminal and Gulosides Bind the N-Terminal

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Bibtex

@article{f00fefdd3441405da5218f6044b727d3,
title = "Epimers Switch Galectin-9 Domain Selectivity: 3 N-Aryl Galactosides Bind the C-Terminal and Gulosides Bind the N-Terminal",
abstract = "A series of 3-deoxy-3-N-arylated-β-d-galactoside and -guloside derivatives have been synthesized by cesium fluoride/trimetylsilylaryl triflate-mediated benzyne generation and N-arylation of 3-deoxy-3-amino-β-d-galactosides and -gulosides, respectively. Evaluation as ligands to galectin-1, 2, 3, 4N (N-terminal domain), 4C (C-terminal domain), 7, 8N, 8C, 9C, and 9N revealed that the galactosides selectively bound galectin-9C, whereas the gulosides selectively bound galectin-9N. Hence, the N-aryl group induces galectin-9 selectivity and the ligand 3C-configuration acts as an epimeric selectivity switch between the two domains of galectin-9. Furthermore, MD simulations revealed that galacto derivatives in galectin-9C and gulo derivatives in galectin-9N find stable poses with specific interactions, which proposes a possible explanation to the gal/gulo 9C/9N selectivity.",
keywords = "epimers, Galactose, galectin-9, gulose, N-phenyl, selectivity",
author = "Mukul Mahanti and Pal, {Kumar Bhaskar} and Sundin, {Anders P.} and Hakon Leffler and Nilsson, {Ulf J.}",
year = "2020",
doi = "10.1021/acsmedchemlett.9b00396",
language = "English",
volume = "11",
pages = "34--39",
journal = "ACS Medicinal Chemistry Letters",
issn = "1948-5875",
publisher = "The American Chemical Society (ACS)",
number = "1",

}