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Synthesis and evaluation of amino-modified α-GalCer analogues

Synthesis and evaluation of amino-modified α-GalCer analogues
Synthesis and evaluation of amino-modified α-GalCer analogues
α-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.
1523-7060
2928-2931
Trappeniers, Matthias
003338a8-2d89-453c-86ee-67c7464e1ac3
Chofor, René
5dcb80fd-3bf5-46ec-b31f-3b0972f400aa
Aspeslagh, Sandrine
7bfd6603-8c2a-435a-b9b9-ce5b8e071621
Li, Yali
d5937fd8-6431-43fb-8a8a-fb5143b2656f
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Zajonc, Dirk M.
47798551-44dd-4b1f-ba3d-f0b3d40f3b86
Elewaut, Dirk
98c0d9e0-e559-4f19-8a56-573fee3da83e
Calenbergh, Serge Van
9a8e80de-780b-4b36-abb4-9c2b35cfd09d
Trappeniers, Matthias
003338a8-2d89-453c-86ee-67c7464e1ac3
Chofor, René
5dcb80fd-3bf5-46ec-b31f-3b0972f400aa
Aspeslagh, Sandrine
7bfd6603-8c2a-435a-b9b9-ce5b8e071621
Li, Yali
d5937fd8-6431-43fb-8a8a-fb5143b2656f
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Zajonc, Dirk M.
47798551-44dd-4b1f-ba3d-f0b3d40f3b86
Elewaut, Dirk
98c0d9e0-e559-4f19-8a56-573fee3da83e
Calenbergh, Serge Van
9a8e80de-780b-4b36-abb4-9c2b35cfd09d

Trappeniers, Matthias, Chofor, René, Aspeslagh, Sandrine, Li, Yali, Linclau, Bruno, Zajonc, Dirk M., Elewaut, Dirk and Calenbergh, Serge Van (2010) Synthesis and evaluation of amino-modified α-GalCer analogues. Organic Letters, 12 (13), 2928-2931. (doi:10.1021/ol100934z).

Record type: Article

Abstract

α-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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Published date: June 2010

Identifiers

Local EPrints ID: 170453
URI: http://eprints.soton.ac.uk/id/eprint/170453
ISSN: 1523-7060
PURE UUID: 073cbb52-db2c-476e-afe3-a25e07046d93
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170

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Date deposited: 06 Jan 2011 16:52
Last modified: 07 Oct 2020 07:55

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Contributors

Author: Matthias Trappeniers
Author: René Chofor
Author: Sandrine Aspeslagh
Author: Yali Li
Author: Bruno Linclau ORCID iD
Author: Dirk M. Zajonc
Author: Dirk Elewaut
Author: Serge Van Calenbergh

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