Synthesis of an isotopically-labelled antarctic fish antifre

Details of Research

TitleSynthesis of an isotopically-labelled antarctic fish antifreeze glycoprotein probeAbstractAntifreeze 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. © 2011 CSIRO.AcknowledgementsThis research was supported by the Human Frontier Science Program (grant RGP003/2009-C). The authors thank Dr Nicole Miller for assistance in the synthesis of tetra-O-acetyl-2-azido-2-deoxygalactose.

Details

1st AuthorWojnar, J.AuthorWojnar, J.Evans, C.Devries, A.Brimble, M.Year2011JournalAustralian Journal of ChemistryVolume64Number6Pages723-731DOI10.1071/CH10464URLhttps://www.scopus.com/inward/recor.....a038588ff629ebd00c1ebb291KeywordsAmino acid building blocksAntifreeze glycoproteinExocrine pancreasGlycosylatedOptimized synthesisSub-zero temperaturesThreonine residuesAmino acid building blocksAntifreeze glycoproteinExocrine pancreasGlycosylatedOptimized synthesisSub-zero temperaturesThreonine residues, Amino acidsGlycoproteinsMass spectrometrySeawaterAmino acidsDrug productsGlycoproteinsMass spectrometryProbes, ProbesFish, rank3ProgrammeK014

Other

TypeArticleCitationWojnar, J., Evans, C., Devries, A. and Brimble, M. (2011). Synthesis of an isotopically-labelled antarctic fish antifreeze glycoprotein probe. Australian Journal of Chemistry, 64(6): 723-731 doi:10.1071/CH10464 IdentifierWojnar2011Relevancerank3

Start typing here to find a location	Latitude	Longitude	Zoom	Actions

loading google map....

Save Cancel