2′-Linking of Lipids and Other Functions to Uridine through 1,2,3-Triazoles and Membrane Anchoring of the Amphiphilic Products

Autor:	Holger A. Scheidt, Oliver Kaczmarek, David Föse, Sebastian Karsten, Andreas Bunge, Daniel Huster, Jürgen Liebscher, Anna Arbuzova
Rok vydání:	2010
Předmět:	Stereochemistry Organic Chemistry Triazole Phospholipid Uracil Nuclear magnetic resonance spectroscopy Uridine chemistry.chemical_compound Membrane chemistry Amphiphile Ribose lipids (amino acids peptides and proteins) Physical and Theoretical Chemistry
Zdroj:	European Journal of Organic Chemistry. 2010:1579-1586
ISSN:	1099-0690 1434-193X
DOI:	10.1002/ejoc.200901073
Popis:	A straightforward synthesis of 2′-functionalized uridines was developed based on a Cu-catalyzed cycloaddition of 2′-azido-2′-deoxyuridine and functionalized alkynes. The functions comprise biochemically important groups such as lipids, a fluorescent marker (Cy5 analogue), pentaacetylglucose, lysine and biotin, and are linked to the 2′-position of uridine by a 1,2,3-triazole ring. A number of NMR spectroscopic investigations revealed that the lipidated 2′-triazolyl-2′-deoxyuridines anchor themselves in the phospholipid membranes without affecting the molecular order in the double layers; the polar moieties – uracil, ribose and triazole – are located in the lipid/water interface of the membrane.
Databáze:	OpenAIRE
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