Synthesis and evaluation of linear CuAAC-oligomerized antifreeze neo-glycopeptides (original) (raw)

van der Wal, Steffen, Capicciotti, Chantelle J., Rontogianni, Stamatia, Ben, Robert N. and Liskamp, Rob M.J. ORCID: https://orcid.org/0000-0001-8897-8975(2014) Synthesis and evaluation of linear CuAAC-oligomerized antifreeze neo-glycopeptides.MedChemComm, 5(8), pp. 1159-1165. (doi: 10.1039/c4md00013g)

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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.

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