Synthesis of an Isotopically-labelled Antarctic Fish Antifreeze Glycoprotein Probe
Antifreeze glycoproteins (AFGPs) are glycosylated polypeptides produced by Antarctic and Arctic fishes, which allow them to survive in seawater at sub-zero temperatures. An investigation into the postulated enteric uptake of AFGP synthesized in the exocrine pancreas of Antarctic fishes required a cu...
Published in: | Australian Journal of Chemistry |
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Main Authors: | , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
CSIRO PUBLISHING
2011
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Subjects: | |
Online Access: | http://hdl.handle.net/2292/7982 https://doi.org/10.1071/CH10464 |
Summary: | Antifreeze glycoproteins (AFGPs) are glycosylated polypeptides produced by Antarctic and Arctic fishes, which allow them to survive in seawater at sub-zero temperatures. An investigation into the postulated enteric uptake of AFGP synthesized in the exocrine pancreas of Antarctic fishes required a custom-prepared AFGP probe that incorporated seven isotopically-labelled Ala residues for detection by mass spectrometry. The AFGPs are composed of a repetitive three amino acid unit (Ala-Ala-Thr), in which the threonine residue is glycosylated with the disaccharide β-d-Gal-(1→3)-α-d-GalNAc. The synthesis of isotopically-labelled AFGP8 (1), as well as the optimized synthesis of the protected glycosylated amino acid building block 2, is reported. |
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