Antifreeze glycopeptide analogues: microwave-enhanced synthesis and functional studies

Heggemann C, Budke C, Schomburg B, Majer Z, Wissbrock M, Koop T, Sewald N (2010)
AMINO ACIDS 38(1): 213-222.

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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 alpha-D-galactosyl(1-3)-beta-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.
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Heggemann C, Budke C, Schomburg B, et al. Antifreeze glycopeptide analogues: microwave-enhanced synthesis and functional studies. AMINO ACIDS. 2010;38(1):213-222.
Heggemann, C., Budke, C., Schomburg, B., Majer, Z., Wissbrock, M., Koop, T., & Sewald, N. (2010). Antifreeze glycopeptide analogues: microwave-enhanced synthesis and functional studies. AMINO ACIDS, 38(1), 213-222.
Heggemann, C., Budke, C., Schomburg, B., Majer, Z., Wissbrock, M., Koop, T., and Sewald, N. (2010). Antifreeze glycopeptide analogues: microwave-enhanced synthesis and functional studies. AMINO ACIDS 38, 213-222.
Heggemann, C., et al., 2010. Antifreeze glycopeptide analogues: microwave-enhanced synthesis and functional studies. AMINO ACIDS, 38(1), p 213-222.
C. Heggemann, et al., “Antifreeze glycopeptide analogues: microwave-enhanced synthesis and functional studies”, AMINO ACIDS, vol. 38, 2010, pp. 213-222.
Heggemann, C., Budke, C., Schomburg, B., Majer, Z., Wissbrock, M., Koop, T., Sewald, N.: Antifreeze glycopeptide analogues: microwave-enhanced synthesis and functional studies. AMINO ACIDS. 38, 213-222 (2010).
Heggemann, Carolin, Budke, Carsten, Schomburg, Benjamin, Majer, Zsuzsa, Wissbrock, Marco, Koop, Thomas, and Sewald, Norbert. “Antifreeze glycopeptide analogues: microwave-enhanced synthesis and functional studies”. AMINO ACIDS 38.1 (2010): 213-222.
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11 Citations in Europe PMC

Data provided by Europe PubMed Central.

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Synthesis of peptides and glycopeptides with polyproline II helical topology as potential antifreeze molecules.
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Nagel L, Budke C, Erdmann RS, Dreyer A, Wennemers H, Koop T, Sewald N., Chemistry 18(40), 2012
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Microwave heating in solid-phase peptide synthesis.
Pedersen SL, Tofteng AP, Malik L, Jensen KJ., Chem Soc Rev 41(5), 2012
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Nagel L, Plattner C, Budke C, Majer Z, DeVries AL, Berkemeier T, Koop T, Sewald N., Amino Acids 41(3), 2011
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Friligou I, Papadimitriou E, Gatos D, Matsoukas J, Tselios T., Amino Acids 40(5), 2011
PMID: 20872260
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Jimenez-Castells C, Defaus S, Andreu D, Gutierrez-Gallego R., Biomol Concepts 1(1), 2010
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