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Issue 30, 2013
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Chemical synthesis of a masked analogue of the fish antifreeze potentiating protein (AFPP)

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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.

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

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Publication details

The article was received on 23 May 2013, accepted on 12 Jun 2013 and first published on 13 Jun 2013


Article type: Paper
DOI: 10.1039/C3OB41066H
Citation: Org. Biomol. Chem., 2013,11, 4935-4942
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    Chemical synthesis of a masked analogue of the fish antifreeze potentiating protein (AFPP)

    S. Yang, J. M. Wojnar, P. W. R. Harris, A. L. DeVries, C. W. Evans and M. A. Brimble, Org. Biomol. Chem., 2013, 11, 4935
    DOI: 10.1039/C3OB41066H

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