Issue 8, 2014

Synthesis and evaluation of linear CuAAC-oligomerized antifreeze neo-glycopeptides

Abstract

Antifreeze glycoproteins (AFGPs) are important naturally occurring biological antifreezes that lower the freezing point of a solution, thereby preventing uncontrolled ice growth. These compounds also inhibit ice recrystallization. Described in this paper is a synthetic antifreeze glycopeptide-based polymer synthesized from an azide/alkyne glycopeptide building block by partial reduction of the azide and subsequent copper catalyzed azide alkyne cycloaddition (CuAAC) polymerization to obtain linear oligomers. To compare the activity with native AFGPs, a linear dodecapeptide (oligomer with four repeating units) was synthesized and isolated which had a comparable length to AFGP-8, the lowest molecular mass glycoprotein AFGP found in nature. In terms of ice recrystallization inhibition (IRI) activity, the triazole-based oligomers displayed only modest IRI activity compared with AFGP-8 and a previously described carbon-linked AFGP analogue. However, CD spectroscopy showed that the triazole-based tetramer possessed a similar secondary structure to the related amide based carbon-linked AFGP tetramer based on AFGP-8.

Graphical abstract: Synthesis and evaluation of linear CuAAC-oligomerized antifreeze neo-glycopeptides

Supplementary files

Article information

Article type
Concise Article
Submitted
09 Jan 2014
Accepted
25 Feb 2014
First published
26 Feb 2014

Med. Chem. Commun., 2014,5, 1159-1165

Synthesis and evaluation of linear CuAAC-oligomerized antifreeze neo-glycopeptides

S. van der Wal, C. J. Capicciotti, S. Rontogianni, R. N. Ben and R. M. J. Liskamp, Med. Chem. Commun., 2014, 5, 1159 DOI: 10.1039/C4MD00013G

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