Synthesis and antifreeze activity of fish antifreeze glycoproteins and their analogues

Peltier, Raoul; Brimble, Margaret A.; Wojnar, Joanna M.; Williams, David E.; Evans, Clive W.; DeVries, Arthur L.

doi:10.1039/c0sc00194e

Cited by 64 publications

(52 citation statements)

References 105 publications

(152 reference statements)

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“…In adapting to this threat, Antarctic notothenioids have evolved a protective mechanism centred on the synthesis of antifreeze glycoproteins (AFGPs), which limit the lethal effects of ice by adsorbing to ice crystals and inhibiting their growth in vivo (DeVries 1988;Peltier et al 2010;Evans et al 2011). During the first few months of their lives, Pleuragramma larvae present a significant paradox because their antifreeze levels are insufficient to prevent freezing .…”

Section: Introductionmentioning

confidence: 99%

Metabolic and behavioural adaptations during early development of the Antarctic silverfish, Pleuragramma antarcticum

et al. 2011

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The Antarctic silverfish Pleuragramma antarcticum is a keystone species in the Ross Sea ecosystem, providing one of the major links between lower and higher trophic levels. Despite the importance of this species, surprisingly little is known of its early development and behaviour. Here, we determine the metabolic capacity of Pleuragramma embryonated eggs and larvae and make comparisons with developing stages of another notothenioid, the naked dragonfish Gymnodraco acuticeps. We also show that although large numbers of embryonated eggs of Pleuragramma are found floating among the platelet ice of Terra Nova Bay, they are able to sink prior to hatching in late spring, likely reducing the risk of exposure to the potentially lethal, ice-laden surface environment. Applying Stoke's law, we determine the change in density required for embryonated eggs to sink at the measured rate and then consider possible mechanisms by which this might occur. Significantly, newly hatched larvae are positively gravitactic and negatively phototactic, such that their swimming behaviour also directs them away from the risk of freezing in the icy surface waters. Measurement of the acute thermal tolerance shows that Pleuragramma larvae have, on average, a sustainable swimming performance breadth of about 17°C, which is significantly greater than that of other adult notothenioids. Although it lacks significant antifreeze capacity in its early developmental stages, Pleuragramma has other attributes that may ensure survival over a wider range of environmental temperatures than other more stenothermal Antarctic notothenioids. How it might adapt to prolonged environmental change arising from phenomena such as global warming, however, requires further investigation.

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Section: Introductionmentioning

confidence: 99%

Metabolic and behavioural adaptations during early development of the Antarctic silverfish, Pleuragramma antarcticum

et al. 2011

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“…In addition, AF(G)Ps cannot be easily obtained using bacterial recombinant expression because of the required glycosylation. Furthermore, to the best of our knowledge, there are only three reported syntheses of AF(G)Ps because of the difficulty of installing the correct disaccharide moiety, and have only succeeded on a small scale [12][13][14] . The second problem is that the majority of attempts at cryopreservation using AF(G)Ps and AFPs have shown minimal benefit, and in most cases a decrease in cell recovery has been observed 11,15,16 .…”

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confidence: 99%

“…However, there are several challenges, which have been encountered when using these materials. The first is availability as AF(G)Ps and the closely related antifreeze proteins (AFPs) can only be isolated in very small quantities from their native sources 12 . In addition, AF(G)Ps cannot be easily obtained using bacterial recombinant expression because of the required glycosylation.…”

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confidence: 99%

Synthetic polymers enable non-vitreous cellular cryopreservation by reducing ice crystal growth during thawing

et al. 2014

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The cryopreservation of cells, tissue and organs is fundamental to modern biotechnology, transplantation medicine and chemical biology. The current state-of-the-art method of cryopreservation is the addition of large amounts of organic solvents such as glycerol or dimethyl sulfoxide, to promote vitrification and prevent ice formation. Here we employ a synthetic, biomimetic, polymer, which is capable of slowing the growth of ice crystals in a manner similar to antifreeze (glyco)proteins to enhance the cryopreservation of sheep and human red blood cells. We find that only 0.1 wt% of the polymer is required to attain significant cell recovery post freezing, compared with over 20 wt% required for solvent-based strategies. These results demonstrate that synthetic antifreeze (glyco)protein mimics could have a crucial role in modern regenerative medicine to improve the storage and distribution of biological material for transplantation.

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“…AFGPs are mucin-type glycoprotein natural products isolated from select Arctic and Antarctic fish, where they play a critical role in preventing the growth of ice crystals. Structurally, AFGPs are composed of multiple copies of the repeating tripeptide Ala-Thr-Ala/Pro, in which each Thr residue is α-O-linked to the disaccharide β-D-galactosyl-(1!3)-α-N-acetyl-D-galactosamine (Scheme 18) and range in size from 4 to 50 repeat units [84,85]. In an effort to access large quantities of homogeneous AFGPs for biological studies and applications in materials science, the authors designed a convergent ligation approach to homogeneous AFGPs bearing between 4 and 32 repeat units.…”

Section: Ligation-desulfurization In Protein Synthesismentioning

confidence: 99%

Modern Extensions of Native Chemical Ligation for Chemical Protein Synthesis

Malins

Payne

2014

Protein Ligation and Total Synthesis I

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Over the past 20 years, native chemical ligation has facilitated the synthesis of numerous complex peptide and protein targets, with and without post-translational modifications, as well as the design and construction of a variety of engineered protein variants. This powerful methodology has also served as a platform for the development of related chemoselective ligation technologies which have greatly expanded the scope and flexibility of ligation chemistry. This chapter details a number of important extensions of the original native chemical ligation manifold, with particular focus on the application of new methods in the total chemical synthesis of proteins. Topics covered include the development of auxiliary-based ligation methods, the post-ligation manipulation of Cys residues, and the synthesis and utility of unnatural amino acid building blocks (bearing reactive thiol or selenol functionalities) in chemoselective ligation chemistry. Contemporary applications of these techniques to the total chemical synthesis of peptides and proteins are described.

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Synthesis and antifreeze activity of fish antifreeze glycoproteins and their analogues

Cited by 64 publications

References 105 publications

Metabolic and behavioural adaptations during early development of the Antarctic silverfish, Pleuragramma antarcticum

Metabolic and behavioural adaptations during early development of the Antarctic silverfish, Pleuragramma antarcticum

Synthetic polymers enable non-vitreous cellular cryopreservation by reducing ice crystal growth during thawing

Modern Extensions of Native Chemical Ligation for Chemical Protein Synthesis

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