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

(2017) ORGANIC & BIOMOLECULAR CHEMISTRY . 15(10). p.2217-2225
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Organization
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.
Keywords
BIOLOGICAL-ACTIVITY, GLYCOSIDE ANALOGS, GALACTOSYLCERAMIDE, PROTECTION, CERAMIDE, KRN7000

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Citation

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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.
@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},
}

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