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

Type of publication Peer-reviewed
Publikationsform Original article (peer-reviewed)
Author Picca Giovanni, Probst Markus, Langenegger Simon M, Khorev Oleg, Bütikofer Peter, Menon Anant K, Häner Robert,
Project Molecular identification of lipid transporters for protein glycosylation
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Original article (peer-reviewed)

Journal Beilstein Journal of Organic Chemistry
Volume (Issue) 16
Page(s) 1732 - 1739
Title of proceedings Beilstein Journal of Organic Chemistry
DOI 10.3762/bjoc.16.145

Open Access

URL http://doi.org/10.3762/bjoc.16.145
Type of Open Access Publisher (Gold Open Access)

Abstract

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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