Peptidic Antifreeze Materials: Prospects and Challenges
Abstract
:1. Introduction
2. Structure and Ice-Binding Sites of Antifreeze (Glyco) Proteins
2.1. α-Helical AFPs
2.2. β-Strand AFPs
2.3. Antifreeze Glycoproteins
2.4. Polyproline II Containing AFPs
3. Ice-Binding and Activity
3.1. Ice Plane Recognition
3.2. Thermal Hysteresis
3.3. Ice Recrystallizaiton Inhibition
4. Production of AF(G)Ps and Synthetic Analogues: Design and Chemical Synthesis Approaches
4.1. Molecular Analogues
4.2. de Novo Design and Synthesis
4.3. Cyclic Peptide Analogues
4.4. Classifying Technologies to Aid de Novo Design
5. Applications of AF(G)Ps and Analogues
6. Prospects and Challenges
7. Concluding Remarks
Author Contributions
Funding
Conflicts of Interest
Abbreviations
AF(G)Ps | antifreeze (glyco)proteins |
TH | thermal hysteresis |
IRI | ice recrystallization inhibition |
SPPS | solid-phase peptide synthesis |
IBS | ice-binding site |
PyBOP | benzotriazole-1-yloxytris(pyrrolidino)phosphonium |
DMTMM | 4-(4-6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium |
Fmoc | fluorenylmethyloxycarbonyl |
FIPA | Fluorescence-based ice plane affinity |
TRITC | tetramethylrhodamine |
PDB | Protein Data Bank |
GFP | green fluorescent protein |
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AF(G)P Type | Synthesis Method | Activity Assay | [A] (mg mL−1 and/or μM) | Ref. | |
---|---|---|---|---|---|
Molecular analogues | I | SPPS of mutant wfAFPs (A17L and A20L) substituting the alanine by leucine | TH | 1, 2, 4 and 8 mg mL−1 | [69] |
I | SPPS of analogues substituting threonine (T) residues by serine (S) or valine (V) | TH | 0.5, 1, 1.5, 2, 4, 5.5 and 7 mM | [81] | |
AFGP8 | In-solution coupling of ATA building blocks with DPPA | TH | 10 mg mL−1 | [85] | |
AFGP8 | In-solution coupling of ATA building blocks using DPPA, DMTMM and IIDQ | TH | 10 mg mL−1 | [86] | |
AFGP2 and AFGP8 | Fmoc SPPS of AFGP building blocks, desulfurization of Thz and Cys residues | TH | 5 and 10 mg mL−1 | [87] | |
AFGP8 | Fmoc SPPS coupling with DCC/4-DMAP and PyBOP | Not tested | [88] | ||
AFGP8 | SPPS of AAT building blocks with DPPA resulting in native AFGP molecular analogue | Not tested | [84] | ||
AFGP8 | Automated Fmoc SPPS at 40 °C using TBTU as coupling reagent | TH IRI | 30 and 40 mg mL−1 0.5 μg mL−1 | [94] | |
DcAFP | SPPS of peptide fragments of DcAFP chemically ligated afterwards | TH | 10 mM | [91] | |
de novo Analogues | polyAAK | SPPS of type I analogues based on lysine instead of threonine | TH | from 25 to 250 mg mL−1 | [92] |
polyAAK | TH | 23 and 31 mM | [93] | ||
PPII | SPPS | Cryopres IRI | 200 mM 20 mg mL−1 | [3] | |
PPII | SPPS of Hydroxyproline peptides functionalized with disaccharides | TH IRI | 10 mg mL−1 7 mM | [4] | |
AFGP | SPPS synthesis of AFGP analogues attached to supramolecular organic dyes | TH IRI | 22 mM | [74] | |
AFGP8 | Cyclized AFGP analogues synthetized by SPPS using DPPA | TH | 10 mg mL−1 | [85] | |
AFGP8 | SPPS of C-linked AFGPs to avoid O-linked degradation of disaccharides | Cyropres | From 1 to 5 mg mL−1 | [95] | |
polyGGK | SPPS of poly GGK followed by the attachment of diverse sugar moieties through C-linking | TH | From 5 μM to 0.05 nM | [96] | |
polyGGK | IRI | From 5 μM to 0.05 nM | [97] | ||
DcAFP | SPPS of mutant DcAFP substituting the disulfide bonds for lactam bonds | TH | 10 mM | [91] |
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Surís-Valls, R.; Voets, I.K. Peptidic Antifreeze Materials: Prospects and Challenges. Int. J. Mol. Sci. 2019, 20, 5149. https://doi.org/10.3390/ijms20205149
Surís-Valls R, Voets IK. Peptidic Antifreeze Materials: Prospects and Challenges. International Journal of Molecular Sciences. 2019; 20(20):5149. https://doi.org/10.3390/ijms20205149
Chicago/Turabian StyleSurís-Valls, Romà, and Ilja K. Voets. 2019. "Peptidic Antifreeze Materials: Prospects and Challenges" International Journal of Molecular Sciences 20, no. 20: 5149. https://doi.org/10.3390/ijms20205149