Exploring the self-assembly of glycopeptides using a diphenylalanine scaffold

Rinat Roytman, Lihi Adler-Abramovich, K. S.Ajish Kumar, Ting Chun Kuan, Chun Cheng Lin, Ehud Gazit, Ashraf Brik

Research output: Contribution to journalArticlepeer-review

Abstract

Diphenylalanine, a key building block for organic nanotechnology, forms discrete, rigid and hollow nanotubes that are assembled spontaneously upon their dilution from organic phase into aqueous solution. Here we report the efficient preparation of several S-linked glycosylated diphenylalanine analogues bearing different monosaccharide, di-saccharide and sialic acid residues. The self-assembly studies revealed that these glycopeptides adopted various structures and glycosylation could be a tool to manipulate the self-assembly process. Moreover, the solubility of these analogues was found to be much greater than diphenylalanine, which could open new applications based on these nanostructures.

Original languageEnglish
Pages (from-to)5755-5761
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume9
Issue number16
DOIs
StatePublished - 21 Aug 2011

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