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Ceramide-templated macrolactams : total synthesis and biological evaluation of macrocyclic α-galactosylceramide analogues and their aglycons

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Abstract
We present the total synthesis of macrocyclic analogues of the immunomodulating glycolipid α‐GalCer (KRN7000), along with the corresponding macrocyclic aglycons. Their structures are inspired by the conformation of α‐GalCer when bound to the antigen presenting glycoprotein CD1d. The applied synthesis plan, involving either ring‐closing metathesis or ruthenium‐catalyzed azide‐alkyne cycloaddition for the crucial macrocyclization step, allowed for easy alteration of the ring size of the macrocycles. These compounds constitute a series of novel cyclic glycosphingolipid analogues.
Keywords
ceramides, macrocycles, macrolactams, α-GalCer, immunomodulators, DISCOVERY

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Citation

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MLA
Janssens, Jonas, Johan Van der Eycken, and Serge Van Calenbergh. “Ceramide-templated Macrolactams : Total Synthesis and Biological Evaluation of Macrocyclic Α-galactosylceramide Analogues and Their Aglycons.” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 12 (2019): 2253–2267. Print.
APA
Janssens, Jonas, Van der Eycken, J., & Van Calenbergh, S. (2019). Ceramide-templated macrolactams : total synthesis and biological evaluation of macrocyclic α-galactosylceramide analogues and their aglycons. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 12, 2253–2267.
Chicago author-date
Janssens, Jonas, Johan Van der Eycken, and Serge Van Calenbergh. 2019. “Ceramide-templated Macrolactams : Total Synthesis and Biological Evaluation of Macrocyclic Α-galactosylceramide Analogues and Their Aglycons.” European Journal of Organic Chemistry 12: 2253–2267.
Chicago author-date (all authors)
Janssens, Jonas, Johan Van der Eycken, and Serge Van Calenbergh. 2019. “Ceramide-templated Macrolactams : Total Synthesis and Biological Evaluation of Macrocyclic Α-galactosylceramide Analogues and Their Aglycons.” European Journal of Organic Chemistry 12: 2253–2267.
Vancouver
1.
Janssens J, Van der Eycken J, Van Calenbergh S. Ceramide-templated macrolactams : total synthesis and biological evaluation of macrocyclic α-galactosylceramide analogues and their aglycons. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2019;12:2253–67.
IEEE
[1]
J. Janssens, J. Van der Eycken, and S. Van Calenbergh, “Ceramide-templated macrolactams : total synthesis and biological evaluation of macrocyclic α-galactosylceramide analogues and their aglycons,” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 12, pp. 2253–2267, 2019.
@article{8605998,
  abstract     = {We present the total synthesis of macrocyclic analogues of the immunomodulating glycolipid α‐GalCer (KRN7000), along with the corresponding macrocyclic aglycons. Their structures are inspired by the conformation of α‐GalCer when bound to the antigen presenting glycoprotein CD1d. The applied synthesis plan, involving either ring‐closing metathesis or ruthenium‐catalyzed azide‐alkyne cycloaddition for the crucial macrocyclization step, allowed for easy alteration of the ring size of the macrocycles. These compounds constitute a series of novel cyclic glycosphingolipid analogues.},
  author       = {Janssens, Jonas and Van der Eycken, Johan and Van Calenbergh, Serge},
  issn         = {1434-193X},
  journal      = {EUROPEAN JOURNAL OF ORGANIC CHEMISTRY},
  keywords     = {ceramides,macrocycles,macrolactams,α-GalCer,immunomodulators,DISCOVERY},
  language     = {eng},
  pages        = {2253--2267},
  title        = {Ceramide-templated macrolactams : total synthesis and biological evaluation of macrocyclic α-galactosylceramide analogues and their aglycons},
  url          = {http://dx.doi.org/10.1002/ejoc.201801839},
  volume       = {12},
  year         = {2019},
}

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