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

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.

SUBMITTER: Robinson SA

PROVIDER: S-EPMC8456744 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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

Robinson Sage A SA Yau Jessica J Terabe Masaki M Berzofsky Jay A JA Painter Gavin F GF Compton Benjamin J BJ Larsen David S DS

Organic & biomolecular chemistry 20200401 14

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 ...[more]

PMID: 32219267

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