A1 Refereed original research article in a scientific journal
Synthesis of Biotinylated Multipodal Glycoclusters on a Solid Support
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
Volume: 2012
Issue: 33
First page : 6594
Last page: 6605
Number of pages: 12
ISSN: 1434-193X
DOI: https://doi.org/10.1002/ejoc.201200926
Self-archived copy’s web address: https://research.utu.fi/converis/portal/detail/Publication/2721374
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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