Influence of Sequential Modifications and Carbohydrate Variations in Synthetic AFGP Analogues on Conformation and Antifreeze Activity

Nagel L, Budke C, Erdmann RS, Dreyer A, Wennemers H, Koop T, Sewald N (2012)
Chemistry 18(40): 12783-12793.

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Certain Arctic and Antarctic ectotherm species have developed strategies for survival under low temperature conditions that, among others, consist of antifreeze glycopeptides (AFGP). AFGP form a class of biological antifreeze agents that exhibit the ability to inhibit ice growth in vitro and in vivo and, hence, enable life at temperatures below the freezing point. AFGP usually consist of a varying number of (Ala-Ala-Thr)(n) units (n=4-55) with the disaccharide beta-D-galactosyl-(1 -> 3)-alpha-N-acetyl-d-galactosamine glycosidically attached to every threonine side chain hydroxyl group. AFGP have been shown to adopt polyproline II helical conformation. Although this pattern is highly conserved among different species, microheterogeneity concerning the amino acid composition usually occurs; for example, alanine is occasionally replaced by proline in smaller AFGP. The influence of minor and major sequence mutations on conformation and antifreeze activity of AFGP analogues was investigated by replacement of alanine by proline and glycosylated threonine by glycosylated hydroxyproline. The target compounds were prepared by using microwave-enhanced solid phase peptide synthesis. Furthermore, artificial analogues were obtained by copper-catalyzed azide-alkyne cycloaddition (CuAAC): propargyl glycosides were treated with polyproline helix II-forming peptides comprising (Pro-Azp-Pro)(n) units (n = 2-4) that contained 4-azidoproline (Azp). The conformations of all analogues were examined by circular dichroism (CD). In addition, microphysical analysis was performed to provide information on their inhibitory effect on ice recrystallization.
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Nagel L, Budke C, Erdmann RS, et al. Influence of Sequential Modifications and Carbohydrate Variations in Synthetic AFGP Analogues on Conformation and Antifreeze Activity. Chemistry. 2012;18(40):12783-12793.
Nagel, L., Budke, C., Erdmann, R. S., Dreyer, A., Wennemers, H., Koop, T., & Sewald, N. (2012). Influence of Sequential Modifications and Carbohydrate Variations in Synthetic AFGP Analogues on Conformation and Antifreeze Activity. Chemistry, 18(40), 12783-12793.
Nagel, L., Budke, C., Erdmann, R. S., Dreyer, A., Wennemers, H., Koop, T., and Sewald, N. (2012). Influence of Sequential Modifications and Carbohydrate Variations in Synthetic AFGP Analogues on Conformation and Antifreeze Activity. Chemistry 18, 12783-12793.
Nagel, L., et al., 2012. Influence of Sequential Modifications and Carbohydrate Variations in Synthetic AFGP Analogues on Conformation and Antifreeze Activity. Chemistry, 18(40), p 12783-12793.
L. Nagel, et al., “Influence of Sequential Modifications and Carbohydrate Variations in Synthetic AFGP Analogues on Conformation and Antifreeze Activity”, Chemistry, vol. 18, 2012, pp. 12783-12793.
Nagel, L., Budke, C., Erdmann, R.S., Dreyer, A., Wennemers, H., Koop, T., Sewald, N.: Influence of Sequential Modifications and Carbohydrate Variations in Synthetic AFGP Analogues on Conformation and Antifreeze Activity. Chemistry. 18, 12783-12793 (2012).
Nagel, Lilly, Budke, Carsten, Erdmann, Roman S., Dreyer, Axel, Wennemers, Helma, Koop, Thomas, and Sewald, Norbert. “Influence of Sequential Modifications and Carbohydrate Variations in Synthetic AFGP Analogues on Conformation and Antifreeze Activity”. Chemistry 18.40 (2012): 12783-12793.
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3 Citations in Europe PMC

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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
PMID: 25137353
Antifreeze peptides and glycopeptides, and their derivatives: potential uses in biotechnology.
Bang JK, Lee JH, Murugan RN, Lee SG, Do H, Koh HY, Shim HE, Kim HC, Kim HJ., Mar Drugs 11(6), 2013
PMID: 23752356
Antifreeze glycopeptide diastereomers.
Nagel L, Budke C, Dreyer A, Koop T, Sewald N., Beilstein J Org Chem 8(), 2012
PMID: 23209499

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