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...

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Bibliographic Details
Published in:Australian Journal of Chemistry
Main Authors: Wojnar, JM, Evans, CW, DeVries, AL, Brimble, MA
Format: Article in Journal/Newspaper
Language:English
Published: CSIRO PUBLISHING 2011
Subjects:
MICROWAVE-ASSISTED SYNTHESIS
PHASE PEPTIDE-SYNTHESIS
POLAR FISH
ANOMERIC DEACETYLATION
GLYCOPEPTIDE
EFFICIENT
GLYCOSIDES
HYDROLYSIS
CONVENIENT
STRATEGIES
Antarctic
Arctic
Antarc*
Online Access:http://hdl.handle.net/2292/7982
https://doi.org/10.1071/CH10464
Description
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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