Chemical synthesis of a masked analogue of the fish antifreeze potentiating protein (AFPP)

Sung Hyun Yang, Joanna M. Wojnar, Paul W.R. Harris, Arthur L. Devries, Clive W. Evans, Margaret A. Brimble

Research output: Contribution to journalArticle

Abstract

A recently identified Antarctic fish protein termed antifreeze potentiating protein (AFPP) is thought to act as an adjunct to the previously characterised antifreeze glycoproteins (AFGPs), the two acting together to inhibit ice crystal growth in vivo. Elucidating the functional properties of the new AFPP requires access to large amounts of pure product, but the paucity of natural material necessitates alternative approaches. We therefore embarked on the total chemical synthesis of the AFPP, through a convergent ligation strategy. After many challenges, mostly due to the solubility issues of the peptide fragments, and several revisions of the original synthetic strategy, we have successfully synthesized a masked analogue of AFPP. The key to the successful synthesis was the use of a solubilising tag attached through a hydrolysable linker.

Original languageEnglish (US)
Pages (from-to)4935-4942
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume11
Issue number30
DOIs
StatePublished - Aug 14 2013

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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