Influence of Sequential Modifications and Carbohydrate Variations in Synthetic AFGP Analogues on Conformation and Antifreeze Activity
Abstract 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 an...
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crwiley:10.1002/chem.201202119 2024-06-23T07:45:58+00:00 Influence of Sequential Modifications and Carbohydrate Variations in Synthetic AFGP Analogues on Conformation and Antifreeze Activity Nagel, Lilly Budke, Carsten Erdmann, Roman S. Dreyer, Axel Wennemers, Helma Koop, Thomas Sewald, Norbert 2012 http://dx.doi.org/10.1002/chem.201202119 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchem.201202119 https://onlinelibrary.wiley.com/doi/full/10.1002/chem.201202119 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Chemistry – A European Journal volume 18, issue 40, page 12783-12793 ISSN 0947-6539 1521-3765 journal-article 2012 crwiley https://doi.org/10.1002/chem.201202119 2024-06-04T06:38:21Z Abstract 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 β‐ D ‐galactosyl‐(1→3)‐α‐ 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. Article in Journal/Newspaper Antarc* Antarctic Arctic Wiley Online Library Antarctic Arctic Chemistry – A European Journal 18 40 12783 12793 |
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Wiley Online Library |
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English |
description |
Abstract 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 β‐ D ‐galactosyl‐(1→3)‐α‐ 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. |
format |
Article in Journal/Newspaper |
author |
Nagel, Lilly Budke, Carsten Erdmann, Roman S. Dreyer, Axel Wennemers, Helma Koop, Thomas Sewald, Norbert |
spellingShingle |
Nagel, Lilly Budke, Carsten Erdmann, Roman S. Dreyer, Axel Wennemers, Helma Koop, Thomas Sewald, Norbert Influence of Sequential Modifications and Carbohydrate Variations in Synthetic AFGP Analogues on Conformation and Antifreeze Activity |
author_facet |
Nagel, Lilly Budke, Carsten Erdmann, Roman S. Dreyer, Axel Wennemers, Helma Koop, Thomas Sewald, Norbert |
author_sort |
Nagel, Lilly |
title |
Influence of Sequential Modifications and Carbohydrate Variations in Synthetic AFGP Analogues on Conformation and Antifreeze Activity |
title_short |
Influence of Sequential Modifications and Carbohydrate Variations in Synthetic AFGP Analogues on Conformation and Antifreeze Activity |
title_full |
Influence of Sequential Modifications and Carbohydrate Variations in Synthetic AFGP Analogues on Conformation and Antifreeze Activity |
title_fullStr |
Influence of Sequential Modifications and Carbohydrate Variations in Synthetic AFGP Analogues on Conformation and Antifreeze Activity |
title_full_unstemmed |
Influence of Sequential Modifications and Carbohydrate Variations in Synthetic AFGP Analogues on Conformation and Antifreeze Activity |
title_sort |
influence of sequential modifications and carbohydrate variations in synthetic afgp analogues on conformation and antifreeze activity |
publisher |
Wiley |
publishDate |
2012 |
url |
http://dx.doi.org/10.1002/chem.201202119 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchem.201202119 https://onlinelibrary.wiley.com/doi/full/10.1002/chem.201202119 |
geographic |
Antarctic Arctic |
geographic_facet |
Antarctic Arctic |
genre |
Antarc* Antarctic Arctic |
genre_facet |
Antarc* Antarctic Arctic |
op_source |
Chemistry – A European Journal volume 18, issue 40, page 12783-12793 ISSN 0947-6539 1521-3765 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/chem.201202119 |
container_title |
Chemistry – A European Journal |
container_volume |
18 |
container_issue |
40 |
container_start_page |
12783 |
op_container_end_page |
12793 |
_version_ |
1802643259017658368 |