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Synthetic preparation and immunological evaluation of β-mannosylceramide and related N-acyl analogues

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Abstract

The synthesis of the invariant natural killer (iNK) T cell agonist β-mannosylceramide along with a series of fatty amide analogues is reported. Of the six β-glycosylation protocols investigated, the sulfoxide methodology developed by Crich and co-workers proved to be the most effective where the reaction of a mannosyl sulfoxide and phytosphingosine derivative gave a key glycolipid intermediate as a 95 : 5 mixture of β- to α-anomers in high yield. A series of mannosyl ceramides were evaluated for their ability to activate D32.D3 NKT cells and induce antitumour activity.

Graphical abstract: Synthetic preparation and immunological evaluation of β-mannosylceramide and related N-acyl analogues

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Article information


Submitted
03 Feb 2020
Accepted
17 Mar 2020
First published
17 Mar 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

Synthetic preparation and immunological evaluation of β-mannosylceramide and related N-acyl analogues

S. A. Robinson, J. Yau, M. Terabe, J. A. Berzofsky, G. F. Painter, B. J. Compton and D. S. Larsen, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB00223B

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