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Synthesis of C6′′-modified α-C-GalCer analogues as mouse and human iNKT cell agonists

Joren Guillaume UGent, Toshiyuki Seki, Tine Decruy UGent, Koen Venken UGent, Dirk Elewaut UGent, Moriya Tsuji and Serge Van Calenbergh UGent (2017) ORGANIC & BIOMOLECULAR CHEMISTRY . 15(10). p.2217-2225
abstract
alpha-GalCer analogues that combine known Th1 polarizing C6''-modifications with a C-glycosidic linkage were synthesized. We employed a protecting group strategy that allowed the preparation of both saturated and unsaturated derivatives with variable C6''-substituents. Selected analogues demonstrate promising activity in mice. Interestingly, the introduction of a 6''-O-pyridinylcarbamoyl substituent to alpha-C-GalCer restores its antigenicity in human iNKT cells.
Please use this url to cite or link to this publication:
author
organization
alternative title
Synthesis of C6′′-modified alpha-C-GalCer analogues as mouse and human iNKT cell agonists
year
type
journalArticle (original)
publication status
published
subject
keyword
BIOLOGICAL-ACTIVITY, GLYCOSIDE ANALOGS, GALACTOSYLCERAMIDE, PROTECTION, CERAMIDE, KRN7000
journal title
ORGANIC & BIOMOLECULAR CHEMISTRY
Org. Biomol. Chem.
volume
15
issue
10
pages
2217 - 2225
Web of Science type
Article
Web of Science id
000396149100012
ISSN
1477-0520
1477-0539
DOI
10.1039/c7ob00081b
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
8542037
handle
http://hdl.handle.net/1854/LU-8542037
date created
2017-12-15 10:37:56
date last changed
2018-01-12 10:51:04
@article{8542037,
  abstract     = {alpha-GalCer analogues that combine known Th1 polarizing C6''-modifications with a C-glycosidic linkage were synthesized. We employed a protecting group strategy that allowed the preparation of both saturated and unsaturated derivatives with variable C6''-substituents. Selected analogues demonstrate promising activity in mice. Interestingly, the introduction of a 6''-O-pyridinylcarbamoyl substituent to alpha-C-GalCer restores its antigenicity in human iNKT cells.},
  author       = {Guillaume, Joren and Seki, Toshiyuki and Decruy, Tine and Venken, Koen and Elewaut, Dirk and Tsuji, Moriya and Van Calenbergh, Serge},
  issn         = {1477-0520},
  journal      = {ORGANIC \& BIOMOLECULAR CHEMISTRY },
  keyword      = {BIOLOGICAL-ACTIVITY,GLYCOSIDE ANALOGS,GALACTOSYLCERAMIDE,PROTECTION,CERAMIDE,KRN7000},
  language     = {eng},
  number       = {10},
  pages        = {2217--2225},
  title        = {Synthesis of C6{\textquotesingle}{\textquotesingle}-modified \ensuremath{\alpha}-C-GalCer analogues as mouse and human iNKT cell agonists},
  url          = {http://dx.doi.org/10.1039/c7ob00081b},
  volume       = {15},
  year         = {2017},
}

Chicago
Guillaume, Joren, Toshiyuki Seki, Tine Decruy, Koen Venken, Dirk Elewaut, Moriya Tsuji, and Serge Van Calenbergh. 2017. “Synthesis of C6′′-modified α-C-GalCer Analogues as Mouse and Human iNKT Cell Agonists.” Organic & Biomolecular Chemistry 15 (10): 2217–2225.
APA
Guillaume, J., Seki, T., Decruy, T., Venken, K., Elewaut, D., Tsuji, M., & Van Calenbergh, S. (2017). Synthesis of C6′′-modified α-C-GalCer analogues as mouse and human iNKT cell agonists. ORGANIC & BIOMOLECULAR CHEMISTRY , 15(10), 2217–2225.
Vancouver
1.
Guillaume J, Seki T, Decruy T, Venken K, Elewaut D, Tsuji M, et al. Synthesis of C6′′-modified α-C-GalCer analogues as mouse and human iNKT cell agonists. ORGANIC & BIOMOLECULAR CHEMISTRY . 2017;15(10):2217–25.
MLA
Guillaume, Joren, Toshiyuki Seki, Tine Decruy, et al. “Synthesis of C6′′-modified α-C-GalCer Analogues as Mouse and Human iNKT Cell Agonists.” ORGANIC & BIOMOLECULAR CHEMISTRY 15.10 (2017): 2217–2225. Print.