Antifreeze glycopeptide analogues: Microwave-enhanced synthesis and functional studies

Carolin Heggemann, Carsten Budke, Benjamin Schomburg, Zsuzsa Majer, Marco Wibrock, Thomas Koop, Norbert Sewald

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

Antifreeze glycoproteins enable life at temperatures below the freezing point of physiological solutions. They usually consist of the repetitive tripeptide unit (-Ala-Ala-Thr-) with the disaccharide α-d-galactosyl-(1-3) -β-N-acetyl-d-galactosamine attached to each hydroxyl group of threonine. Monoglycosylated analogues have been synthesized from the corresponding monoglycosylated threonine building block by microwave-assisted solid phase peptide synthesis. This method allows the preparation of analogues containing sequence variations which are not accessible by other synthetic methods. As antifreeze glycoproteins consist of numerous isoforms they are difficult to obtain in pure form from natural sources. The synthetic peptides have been structurally analyzed by CD and NMR spectroscopy in proton exchange experiments revealing a structure as flexible as reported for the native peptides. Microphysical recrystallization tests show an ice structuring influence and ice growth inhibition depending on the concentration, chain length and sequence of the peptides.

Original languageEnglish
Pages (from-to)213-222
Number of pages10
JournalAmino Acids
Volume38
Issue number1
DOIs
Publication statusPublished - Jan 1 2010

Keywords

  • Bioorganic chemistry
  • Circular dichroism
  • Glycopeptides
  • Microwave synthesis
  • Recrystallization

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Organic Chemistry

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    Heggemann, C., Budke, C., Schomburg, B., Majer, Z., Wibrock, M., Koop, T., & Sewald, N. (2010). Antifreeze glycopeptide analogues: Microwave-enhanced synthesis and functional studies. Amino Acids, 38(1), 213-222. https://doi.org/10.1007/s00726-008-0229-0