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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
Author
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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MLA
Guillaume, Joren, et al. “Synthesis of C6′′-Modified α-C-GalCer Analogues as Mouse and Human INKT Cell Agonists.” ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 15, no. 10, 2017, pp. 2217–25, doi:10.1039/c7ob00081b.
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. https://doi.org/10.1039/c7ob00081b
Chicago author-date
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): 2217–25. https://doi.org/10.1039/c7ob00081b.
Chicago author-date (all authors)
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. doi:10.1039/c7ob00081b.
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.
IEEE
[1]
J. Guillaume et al., “Synthesis of C6′′-modified α-C-GalCer analogues as mouse and human iNKT cell agonists,” ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 15, no. 10, pp. 2217–2225, 2017.
@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}},
  keywords     = {{BIOLOGICAL-ACTIVITY,GLYCOSIDE ANALOGS,GALACTOSYLCERAMIDE,PROTECTION,CERAMIDE,KRN7000}},
  language     = {{eng}},
  number       = {{10}},
  pages        = {{2217--2225}},
  title        = {{Synthesis of C6′′-modified α-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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