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Synthesis and evaluation of amino-modified alpha-GalCer analogues. 2010
Matthias Trappeniers, and
René Chofor, and
Sandrine Aspeslagh, and
Yali Li, and
Bruno Linclau, and
Dirk M Zajonc, and
Dirk Elewaut, and
Serge Van Calenbergh
Laboratory for Medicinal Chemistry (FFW), Ghent University, Harelbekestraat 72, 9000 Ghent, Belgium.
Alpha-GalCer analogues featuring a phytoceramide 3- and 4-amino group have been synthesized. A Mitsunobu reaction involving phthalimide was employed for the introduction of the amino groups at the 3- and 4-positions of suitable phytosphingosine-derived precursors. The influence of these modifications on the interaction with the T-cell receptor of NKT cells was investigated, as well as the capacity of the amino-modified analogues to induce a cytokine response after in vivo administration.
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