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

Nagel L, Plattner C, Budke C, Majer Z, DeVries AL, Berkemeier T, Koop T, Sewald N (2011)
AMINO ACIDS 41(3): 719-732.

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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 beta-d-galactosyl-(1 -> 3)-alpha-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.
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Nagel L, Plattner C, Budke C, et al. Synthesis and characterization of natural and modified antifreeze glycopeptides: glycosylated foldamers. AMINO ACIDS. 2011;41(3):719-732.
Nagel, L., Plattner, C., Budke, C., Majer, Z., DeVries, A. L., Berkemeier, T., Koop, T., et al. (2011). Synthesis and characterization of natural and modified antifreeze glycopeptides: glycosylated foldamers. AMINO ACIDS, 41(3), 719-732.
Nagel, L., Plattner, C., Budke, C., Majer, Z., DeVries, A. L., Berkemeier, T., Koop, T., and Sewald, N. (2011). Synthesis and characterization of natural and modified antifreeze glycopeptides: glycosylated foldamers. AMINO ACIDS 41, 719-732.
Nagel, L., et al., 2011. Synthesis and characterization of natural and modified antifreeze glycopeptides: glycosylated foldamers. AMINO ACIDS, 41(3), p 719-732.
L. Nagel, et al., “Synthesis and characterization of natural and modified antifreeze glycopeptides: glycosylated foldamers”, AMINO ACIDS, vol. 41, 2011, pp. 719-732.
Nagel, L., Plattner, C., Budke, C., Majer, Z., DeVries, A.L., Berkemeier, T., Koop, T., Sewald, N.: Synthesis and characterization of natural and modified antifreeze glycopeptides: glycosylated foldamers. AMINO ACIDS. 41, 719-732 (2011).
Nagel, Lilly, Plattner, Carolin, Budke, Carsten, Majer, Zsuzsanna, DeVries, Arthur L., Berkemeier, Thomas, Koop, Thomas, and Sewald, Norbert. “Synthesis and characterization of natural and modified antifreeze glycopeptides: glycosylated foldamers”. AMINO ACIDS 41.3 (2011): 719-732.
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Data provided by Europe PubMed Central.

Perturbation of long-range water dynamics as the mechanism for the antifreeze activity of antifreeze glycoprotein.
Mallajosyula SS, Vanommeslaeghe K, MacKerell AD Jr., J Phys Chem B 118(40), 2014
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