A1 Journal article – refereed
Synthesis of Biotinylated Multipodal Glycoclusters on a Solid Support




List of Authors: Karskela M, von Usedom M, Virta P, Lonnberg H
Publisher: WILEY-V C H VERLAG GMBH
Publication year: 2012
Journal: European Journal of Organic Chemistry
Journal name in source: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Journal acronym: EUR J ORG CHEM
Number in series: 33
Issue number: 33
Number of pages: 12
ISSN: 1434-193X

Abstract
Trivalent glycoconjugates, each bearing a biotin side arm in addition to three different sugar ligands, have been synthesized on a solid support. The conjugates were assembled on an orthogonally protected pentaerythrityl tetramine core that was anchored to the support through a backbone amide linker. Peptide coupling chemistry was applied to elongate three of the branches with beta-alanine and a fully acylated glycosylacetic acid. The fourth branch was levulinoylated and oximated with aminooxy-derivatized D-biotin, followed by acidolytic release into solution. The acyl protecting groups were removed by methoxide-catalyzed transesterification in methanol.


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Last updated on 2019-21-08 at 23:25