Synthesis of Biotinylated Multipodal Glycoclusters on a Solid Support




Karskela M, von Usedom M, Virta P, Lonnberg H

PublisherWILEY-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

DOIhttps://doi.org/10.1002/ejoc.201200926

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.

Last updated on 2024-26-11 at 18:25