Galactosylsphingamides: new α-GalCer analogues to probe the F’-pocket of CD1d

Abstract Invariant Natural Killer T-cells (iNKT-cells) are an attractive target for immune response modulation, as upon CD1d-mediated stimulation with KRN7000, a synthetic α-galactosylceramide, they produce a vast amount of cytokines. Here we present a synthesis that allows swift modification of the...

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Autores principales:	Joren Guillaume, Jing Wang, Jonas Janssens, Soumya G. Remesh, Martijn D. P. Risseeuw, Tine Decruy, Mathy Froeyen, Dirk Elewaut, Dirk M. Zajonc, Serge Van Calenbergh
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2017
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/b6242e5fce344e1e9535e44bda9ee7ff
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spelling	oai:doaj.org-article:b6242e5fce344e1e9535e44bda9ee7ff2021-12-02T12:32:37ZGalactosylsphingamides: new α-GalCer analogues to probe the F’-pocket of CD1d10.1038/s41598-017-04461-72045-2322https://doaj.org/article/b6242e5fce344e1e9535e44bda9ee7ff2017-06-01T00:00:00Zhttps://doi.org/10.1038/s41598-017-04461-7https://doaj.org/toc/2045-2322Abstract Invariant Natural Killer T-cells (iNKT-cells) are an attractive target for immune response modulation, as upon CD1d-mediated stimulation with KRN7000, a synthetic α-galactosylceramide, they produce a vast amount of cytokines. Here we present a synthesis that allows swift modification of the phytosphingosine side chain by amidation of an advanced methyl ester precursor. The resulting KRN7000 derivatives, termed α-galactosylsphingamides, were evaluated for their capacity to stimulate iNKT-cells. While introduction of the amide-motif in the phytosphingosine chain is tolerated for CD1d binding and TCR recognition, the studied α-galactosylsphingamides showed compromised antigenic properties.Joren GuillaumeJing WangJonas JanssensSoumya G. RemeshMartijn D. P. RisseeuwTine DecruyMathy FroeyenDirk ElewautDirk M. ZajoncSerge Van CalenberghNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 7, Iss 1, Pp 1-18 (2017)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Joren Guillaume Jing Wang Jonas Janssens Soumya G. Remesh Martijn D. P. Risseeuw Tine Decruy Mathy Froeyen Dirk Elewaut Dirk M. Zajonc Serge Van Calenbergh Galactosylsphingamides: new α-GalCer analogues to probe the F’-pocket of CD1d
description	Abstract Invariant Natural Killer T-cells (iNKT-cells) are an attractive target for immune response modulation, as upon CD1d-mediated stimulation with KRN7000, a synthetic α-galactosylceramide, they produce a vast amount of cytokines. Here we present a synthesis that allows swift modification of the phytosphingosine side chain by amidation of an advanced methyl ester precursor. The resulting KRN7000 derivatives, termed α-galactosylsphingamides, were evaluated for their capacity to stimulate iNKT-cells. While introduction of the amide-motif in the phytosphingosine chain is tolerated for CD1d binding and TCR recognition, the studied α-galactosylsphingamides showed compromised antigenic properties.
format	article
author	Joren Guillaume Jing Wang Jonas Janssens Soumya G. Remesh Martijn D. P. Risseeuw Tine Decruy Mathy Froeyen Dirk Elewaut Dirk M. Zajonc Serge Van Calenbergh
author_facet	Joren Guillaume Jing Wang Jonas Janssens Soumya G. Remesh Martijn D. P. Risseeuw Tine Decruy Mathy Froeyen Dirk Elewaut Dirk M. Zajonc Serge Van Calenbergh
author_sort	Joren Guillaume
title	Galactosylsphingamides: new α-GalCer analogues to probe the F’-pocket of CD1d
title_short	Galactosylsphingamides: new α-GalCer analogues to probe the F’-pocket of CD1d
title_full	Galactosylsphingamides: new α-GalCer analogues to probe the F’-pocket of CD1d
title_fullStr	Galactosylsphingamides: new α-GalCer analogues to probe the F’-pocket of CD1d
title_full_unstemmed	Galactosylsphingamides: new α-GalCer analogues to probe the F’-pocket of CD1d
title_sort	galactosylsphingamides: new α-galcer analogues to probe the f’-pocket of cd1d
publisher	Nature Portfolio
publishDate	2017
url	https://doaj.org/article/b6242e5fce344e1e9535e44bda9ee7ff
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Galactosylsphingamides: new α-GalCer analogues to probe the F’-pocket of CD1d

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