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Synthesis and evaluation of amino-modified α-GalCer analogues

Matthias Trappeniers UGent, René Chofor UGent, SANDRINE ASPESLAGH UGent, Yali Li, Bruno Linclau, Dirk M Zajonc, Dirk Elewaut UGent and Serge Van Calenbergh UGent (2010) ORGANIC LETTERS. 12(13). p.2928-2931
abstract
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.
Please use this url to cite or link to this publication:
author
organization
alternative title
Synthesis and evaluation of amino-modified alpha-GalCer analogues
year
type
journalArticle (original)
publication status
published
subject
keyword
CERAMIDE, GALACTOSYLCERAMIDES, VARIANTS, RECOGNITION, SPONGE AGELAS-MAURITIANUS, GLYCOLIPIDS, HUMAN CD1D, T-CELL-RECEPTOR
journal title
ORGANIC LETTERS
Org. Lett.
volume
12
issue
13
pages
2928 - 2931
Web of Science type
Article
Web of Science id
000279070100010
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
5.25 (2010)
JCR rank
5/56 (2010)
JCR quartile
1 (2010)
ISSN
1523-7060
DOI
10.1021/ol100934z
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
1095024
handle
http://hdl.handle.net/1854/LU-1095024
date created
2011-01-06 12:04:40
date last changed
2012-09-11 13:11:08
@article{1095024,
  abstract     = {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.},
  author       = {Trappeniers, Matthias and Chofor, Ren{\'e} and ASPESLAGH, SANDRINE and Li, Yali and Linclau, Bruno and Zajonc, Dirk M and Elewaut, Dirk and Van Calenbergh, Serge},
  issn         = {1523-7060},
  journal      = {ORGANIC LETTERS},
  keyword      = {CERAMIDE,GALACTOSYLCERAMIDES,VARIANTS,RECOGNITION,SPONGE AGELAS-MAURITIANUS,GLYCOLIPIDS,HUMAN CD1D,T-CELL-RECEPTOR},
  language     = {eng},
  number       = {13},
  pages        = {2928--2931},
  title        = {Synthesis and evaluation of amino-modified \ensuremath{\alpha}-GalCer analogues},
  url          = {http://dx.doi.org/10.1021/ol100934z},
  volume       = {12},
  year         = {2010},
}

Chicago
Trappeniers, Matthias, René Chofor, Sandrine Aspeslagh, Yali Li, Bruno Linclau, Dirk M Zajonc, Dirk Elewaut, and Serge Van Calenbergh. 2010. “Synthesis and Evaluation of Amino-modified α-GalCer Analogues.” Organic Letters 12 (13): 2928–2931.
APA
Trappeniers, M., Chofor, R., Aspeslagh, S., Li, Y., Linclau, B., Zajonc, D. M., Elewaut, D., et al. (2010). Synthesis and evaluation of amino-modified α-GalCer analogues. ORGANIC LETTERS, 12(13), 2928–2931.
Vancouver
1.
Trappeniers M, Chofor R, Aspeslagh S, Li Y, Linclau B, Zajonc DM, et al. Synthesis and evaluation of amino-modified α-GalCer analogues. ORGANIC LETTERS. 2010;12(13):2928–31.
MLA
Trappeniers, Matthias, René Chofor, Sandrine Aspeslagh, et al. “Synthesis and Evaluation of Amino-modified α-GalCer Analogues.” ORGANIC LETTERS 12.13 (2010): 2928–2931. Print.