Nonenzymatic synthesis of anomerically pure, mannosyl-based molecular probes for scramblase identification studies

Picca, Giovanni; Probst, Markus; Langenegger, Simon M.; Khorev, Oleg; Bütikofer, Peter; Menon, Anant K; Häner, Robert (2020). Nonenzymatic synthesis of anomerically pure, mannosyl-based molecular probes for scramblase identification studies. Beilstein journal of organic chemistry, 16, pp. 1732-1739. Beilstein-Institut 10.3762/bjoc.16.145

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The chemical synthesis of molecular probes to identify and study membrane proteins involved in the biological pathway of protein glycosylation is described. Two short-chain glycolipid analogs that mimic the naturally occurring substrate mannosyl phosphoryl dolichol exhibit either photoreactive and clickable properties or allow the use of a fluorescence readout. Both probes consist of a hydrophilic mannose headgroup that is linked to a citronellol derivative via a phosphodiester bridge. Moreover, a novel phosphoramidite chemistry-based method offers a straightforward approach for the non-enzymatic incorporation of the saccharide moiety in an anomerically pure form.

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