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.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry
04 Faculty of Medicine > Pre-clinic Human Medicine > Institute of Biochemistry and Molecular Medicine

UniBE Contributor:

Picca, Giovanni; Probst, Markus; Langenegger, Simon Matthias; Khorev, Oleg; Bütikofer, Peter and Häner, Robert

Subjects:

500 Science > 570 Life sciences; biology
500 Science > 540 Chemistry
600 Technology > 610 Medicine & health

ISSN:

1860-5397

Publisher:

Beilstein-Institut

Funders:

[4] Swiss National Science Foundation

Language:

English

Submitter:

Robert Häner

Date Deposited:

21 Jul 2020 08:44

Last Modified:

26 Jul 2020 14:35

Publisher DOI:

10.3762/bjoc.16.145

BORIS DOI:

10.7892/boris.145277

URI:

https://boris.unibe.ch/id/eprint/145277

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