Synthesis and characterization of natural and modified antifreeze glycopeptides: Glycosylated foldamers

Lilly Nagel, Carolin Plattner, Carsten Budke, Zsuzsanna Majer, Arthur L. Devries, Thomas Berkemeier, Thomas Koop, Norbert Sewald

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

In Arctic and Antarctic marine regions, where the temperature declines below the colligative freezing point of physiological fluids, efficient biological antifreeze agents are crucial for the survival of polar fish. One group of such agents is classified as antifreeze glycoproteins (AFGP) that usually consist of a varying number (n = 4-55) of [AAT] n -repeating units. The threonine side chain of each unit is glycosidically linked to β-d-galactosyl-(1 → 3)-α-N-acetyl-d-galactosamine. These biopolymers can be considered as biological antifreeze foldamers. A preparative route for stepwise synthesis of AFGP allows for efficient synthesis. The diglycosylated threonine building block was introduced into the peptide using microwave-enhanced solid phase synthesis. By this versatile solid phase approach, glycosylated peptides of varying sequences and lengths could be obtained. Conformational studies of the synthetic AFGP analogs were performed by circular dichroism experiments (CD). Furthermore, the foldamers were analysed microphysically according to their inhibiting effect on ice recrystallization and influence on the crystal habit.

Original languageEnglish
Pages (from-to)719-732
Number of pages14
JournalAmino Acids
Volume41
Issue number3
DOIs
Publication statusPublished - Aug 1 2011

Keywords

  • Bioorganic chemistry
  • Circular dichroism
  • Glycopeptides
  • Ice recrystallization
  • Microwave-enhanced synthesis
  • Solid phase peptide synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Organic Chemistry

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  • Cite this

    Nagel, L., Plattner, C., Budke, C., Majer, Z., Devries, A. L., Berkemeier, T., Koop, T., & Sewald, N. (2011). Synthesis and characterization of natural and modified antifreeze glycopeptides: Glycosylated foldamers. Amino Acids, 41(3), 719-732. https://doi.org/10.1007/s00726-011-0937-8