Synthesis of Biotinylated Multipodal Glycoclusters on a Solid Support
: Karskela M, von Usedom M, Virta P, Lonnberg H
Publisher: WILEY-V C H VERLAG GMBH
: 2012
: European Journal of Organic Chemistry
: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
: EUR J ORG CHEM
: 33
: 2012
: 33
: 6594
: 6605
: 12
: 1434-193X
DOI: https://doi.org/10.1002/ejoc.201200926(external)
: https://research.utu.fi/converis/portal/detail/Publication/2721374(external)
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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