Synthesis and evaluation of amino-modified alpha-GalCer analogues.
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.
Laboratory for Medicinal Chemistry (FFW), Ghent University, Harelbekestraat 72, 9000 Ghent, Belgium.
Matthias
M
Trappeniers
René
R
Chofor
Sandrine
S
Aspeslagh
Yali
Y
Li
Bruno
B
Linclau
Dirk M
DM
Zajonc
Dirk
D
Elewaut
Serge
S
Van Calenbergh
D005699:Galactosylceramides / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D005699:Galactosylceramides