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Synthesis and in vitro evaluation of ?-GalCer epimers

Synthesis and in vitro evaluation of ?-GalCer epimers
Synthesis and in vitro evaluation of ?-GalCer epimers
?-GalCer (also known as KRN7000) is an immunomodulatory glycolipid that is known to potently activate invariant natural killer T (NKT) cells upon CD1d-mediated stimulation. Because Th1 and Th2 cytokines, which are released after ?-GalCer presentation, antagonize each other's effects, ?-GalCer analogues that induce a biased Th1/Th2 response are highly awaited. In this context, we report the synthesis and in vitro evaluation of ?-Gal-D-xylo-Cer and two ?-Gal-L-lyxo-Cer analogues, one with the natural acyl chain, the other with a truncated chain.
?-galactosylceramide, cytokines, epimers, glycolipids, NKT cells
1860-7179
1061-1070
Trappeniers, Matthias
003338a8-2d89-453c-86ee-67c7464e1ac3
Goormans, Stijn
b51ab85e-b3cc-4ae3-b02d-322d15400b86
Van Beneden, Katrien
d8fc2c97-163b-4422-a513-34a08745a00c
Decruy, Tine
0d799625-7310-423a-b7a7-6ece86b8ea1a
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Al-Shamkhani, Aymen
0a40b3ce-9d71-4d41-9369-7212f0a84504
Elliott, Tim
16670fa8-c2f9-477a-91df-7c9e5b453e0e
Ottensmeier, Christian
42b8a398-baac-4843-a3d6-056225675797
Werner, Joern M.
fba7b358-19b5-437f-bf17-47250953b1d9
Elewaut, Dirk
98c0d9e0-e559-4f19-8a56-573fee3da83e
Van Calenbergh, Serge
9587a6e2-b48b-4f79-807d-b889c7a1d9d6
Trappeniers, Matthias
003338a8-2d89-453c-86ee-67c7464e1ac3
Goormans, Stijn
b51ab85e-b3cc-4ae3-b02d-322d15400b86
Van Beneden, Katrien
d8fc2c97-163b-4422-a513-34a08745a00c
Decruy, Tine
0d799625-7310-423a-b7a7-6ece86b8ea1a
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Al-Shamkhani, Aymen
0a40b3ce-9d71-4d41-9369-7212f0a84504
Elliott, Tim
16670fa8-c2f9-477a-91df-7c9e5b453e0e
Ottensmeier, Christian
42b8a398-baac-4843-a3d6-056225675797
Werner, Joern M.
fba7b358-19b5-437f-bf17-47250953b1d9
Elewaut, Dirk
98c0d9e0-e559-4f19-8a56-573fee3da83e
Van Calenbergh, Serge
9587a6e2-b48b-4f79-807d-b889c7a1d9d6

Trappeniers, Matthias, Goormans, Stijn, Van Beneden, Katrien, Decruy, Tine, Linclau, Bruno, Al-Shamkhani, Aymen, Elliott, Tim, Ottensmeier, Christian, Werner, Joern M., Elewaut, Dirk and Van Calenbergh, Serge (2008) Synthesis and in vitro evaluation of ?-GalCer epimers ChemMedChem, 3, (7), pp. 1061-1070. (doi:10.1002/cmdc.200800021).

Record type: Article

Abstract

?-GalCer (also known as KRN7000) is an immunomodulatory glycolipid that is known to potently activate invariant natural killer T (NKT) cells upon CD1d-mediated stimulation. Because Th1 and Th2 cytokines, which are released after ?-GalCer presentation, antagonize each other's effects, ?-GalCer analogues that induce a biased Th1/Th2 response are highly awaited. In this context, we report the synthesis and in vitro evaluation of ?-Gal-D-xylo-Cer and two ?-Gal-L-lyxo-Cer analogues, one with the natural acyl chain, the other with a truncated chain.

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More information

Published date: 14 July 2008
Keywords: ?-galactosylceramide, cytokines, epimers, glycolipids, NKT cells

Identifiers

Local EPrints ID: 148347
URI: http://eprints.soton.ac.uk/id/eprint/148347
ISSN: 1860-7179
PURE UUID: 84182c2c-f3b4-4e7f-9659-40cda0b50548
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170
ORCID for Tim Elliott: ORCID iD orcid.org/0000-0003-1097-0222

Catalogue record

Date deposited: 27 Apr 2010 15:48
Last modified: 18 Jul 2017 19:32

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Contributors

Author: Matthias Trappeniers
Author: Stijn Goormans
Author: Katrien Van Beneden
Author: Tine Decruy
Author: Bruno Linclau ORCID iD
Author: Tim Elliott ORCID iD
Author: Joern M. Werner
Author: Dirk Elewaut
Author: Serge Van Calenbergh

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