Antifreeze Glycoproteins: Elucidation of the Structural Motifs That Are Essential for Antifreeze Activity

Tachibana, Yuki; Fletcher, George P.; Fujitani, Naoki; Tsuda, Sakae; Monde, Kenji; Nishimura, Shin‐Ichiro

doi:10.1002/anie.200353110

Cited by 196 publications

(214 citation statements)

References 33 publications

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“…The fish antifreeze proteins, which are the most studied ones, fall into two groups: antifreeze proteins (AFP) and antifreeze glycoproteins (AFGP). The structure and properties of these proteins and the mechanism of inhibition of ice crystal growth have been reviewed (33,34,(36)(37)(38)(39)(40)(41). These proteins are present in millimolar concentrations in the plasma of Antarctic fishes and up to 35 mg/mL in some cases.…”

Section: Discussionmentioning

confidence: 99%

Inhibition of Ice Crystal Growth in Ice Cream Mix by Gelatin Hydrolysate

Damodaran

2007

J. Agric. Food Chem.

125

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The inhibition of ice crystal growth in ice cream mix by gelatin hydrolysate produced by papain action was studied. The ice crystal growth was monitored by thermal cycling between -14 and -12°C at a rate of one cycle per 3 min. It is shown that the hydrolysate fraction containing peptides in the molecular weight range of about 2000 -5000 Da exhibited the highest inhibitory activity on ice crystal growth in ice cream mix, whereas fractions containing peptides greater than 7000 Da did not inhibit ice crystal growth. The size distribution of gelatin peptides formed in the hydrolysate was influenced by the pH of hydrolysis. The optimum hydrolysis conditions for producing peptides with maximum ice crystal growth inhibitory activity was pH 7 at 37°C for 10 min at a papain to gelatin ratio of 1:100. However, this may depend on the type and source of gelatin. The possible mechanism of ice crystal growth inhibition by peptides from gelatin is discussed. Molecular modeling of model gelatin peptides revealed that they form an oxygen triad plane at the C-terminus with oxygen-oxygen distances similar to those found in ice nuclei. Binding of this oxygen triad plane to the prism face of ice nuclei via hydrogen bonding appears to be the mechanism by which gelatin hydrolysate might be inhibiting ice crystal growth in ice cream mix.

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Section: Discussionmentioning

confidence: 99%

Inhibition of Ice Crystal Growth in Ice Cream Mix by Gelatin Hydrolysate

Damodaran

2007

J. Agric. Food Chem.

125

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“…Recently, Nishimura and co-workers reported a paramount work providing critical structure-activity data to understand the mechanism of ice growth inhibition and to rationalize the design of AFGP mimics. [5] On the other hand, the synthesis of different glycosylated analogues with the [Thr(α-GalNAc)-Ala-Ala] n sequence has been reported, the underlying amino acid show perpendicular orientation of the sugar with respect to the peptide moiety. This structural feature, together with the rigidity of the Thr-containing glycopeptide, makes this system unique to structure the water molecules of its first hydration shell.…”

Section: Introductionmentioning

confidence: 98%

Dynamics and Hydration Properties of Small Antifreeze‐Like Glycopeptides Containing Non‐Natural Amino Acids

et al. 2010

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Novel studies on the synthesis and conformation in aqueous solution of three antifreeze‐like glycopeptides containing the sequence Xaa(α‐GalNAc)‐Ala‐Ala, with Xaa being threonine (Thr) or the non‐natural amino acids α‐methylserine (MeSer) or α‐methylthreonine (MeThr), are reported. The study has combined NMR experiments with molecular dynamics simulations. Whereas the Thr derivative is rather rigid in solution and exhibits an extended conformation for the backbone, the non‐natural glycopeptides are fairly flexible and show random coil structures for the peptide sequence. On the other hand, only those glycopeptides with a methyl group at Cβ of the underlying amino acid show perpendicular orientation of the sugar with respect to the peptide moiety. This structural feature, together with the rigidity of the Thr‐containing glycopeptide, makes this system unique to structure the water molecules of its first hydration shell. In addition, despite its chemical similarity, the different observed conformational behaviors of all these molecules, as well as the differences in their dynamics and hydration properties, make them suitable systems to shed light on the key factors that govern antifreeze activity.

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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%

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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Antifreeze Glycoproteins: Elucidation of the Structural Motifs That Are Essential for Antifreeze Activity

Cited by 196 publications

References 33 publications

Inhibition of Ice Crystal Growth in Ice Cream Mix by Gelatin Hydrolysate

Inhibition of Ice Crystal Growth in Ice Cream Mix by Gelatin Hydrolysate

Dynamics and Hydration Properties of Small Antifreeze‐Like Glycopeptides Containing Non‐Natural Amino Acids

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

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