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Chemical Structure| 556-50-3 Chemical Structure| 556-50-3
Chemical Structure| 556-50-3

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Glycylglycine is the dipeptide of glycine, it can be used as a buffer for biological systems, as well as in the synthesis of more complex peptides.

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Product Citations

Farazi, Shegufta ;

Abstract: Folding polymers into well-defined nanostructures in aqueous solutions is critical for mimicking the structure and functionalities of naturally occurring proteins. Peptide motifs, such as di(phenylalanine) (FF), can be used to guide intramolecular collapse of polymer chains in a versatile and thermally reversible way in aqueous conditions, but there have been relatively few studies exploring their use to direct the folding of single chain polymer nanoparticles (SCNPs) to date. In this Thesis, it is shown that confinement of L-di(phenylalanine) (LFF) moieties (10 mol.%) within the central block of a triblock copolymer results in considerable collapse relative to polymer chains without any peptide. Controlled folding with other peptide motifs, such as KVLFF and LVV was difficult because the hydrogen bonding and β-sheet interactions for KVLFF was too strong to prevent multichain aggregation, whereas with LVV, the lack of aromatic groups and hydrophobicity resulted in less stable -sheet interactions which also resulted in aggregation over compact SCNPs. Using a recently developed automated synthesis of multiblock peptide–DMA copolymers, we show that by controlling the position of LFF, in blocks furthest away in a hexablock polymer, significant compaction relative to DMA homopolymer can be achieved. Heterochiral polymers with DFF and LFF positioned in blocks furthest away in the polymer, produced more compact SCNPs (~1.6 nm) than homochiral LFF polymers (~1.9 nm), which indicated that weaker -sheet interactions of heterochiral peptide motifs afford the most thermodynamically stable conformation of SCNPs. Thus, with these dynamic and hydrophobic LFF and DFF motifs, globular collapse of polymer chains ( v = 0.38-42), mimicking globular proteins ( v = 0.33), can be induced at relatively low peptide densities (10 mol.%) compared to previously reported FF copolymers and SCNPs ( v ≧0.48). The tunability offered by both the sequence of the peptide and its position within the polymer makes these folding motifs ideal for preparing water soluble and biocompatible SCNPs. Unfortunately, the biological behaviour of biocompatible SCNPs is poorly understood and there is conflicting evidence in the literature about how they are taken up into cells. To solve this knowledge gap, we applied Forster resonance energy transfer (FRET) on our peptide-folded SCNPs to study their uptake mechanism in breast cancer cell line (MCF-7). Rapid and considerable cell association was noted for monodisperse SCNPs (~13-15 nm), and further visualisation with confocal laser scanning microscopy (CLSM), showed strong uptake of monodisperse particles at both 37℃ and 4℃, indicating that passive diffusion through the cell membrane can take place. By contrast, larger aggregated particles (~ 280 nm) of the same polymer showed a slower rate of cell association and uptake via endocytosis alone. These results were confirmed by fluorescence lifetime imaging microscopy (FLIM-FRET) which showed both sets of particles to have low FRET transfer efficiency (%) once inside MCF-7 cells. This demonstrates that the aggregated particles become destabilised within the cellular environment, forcing disassembly. These results highlight the value of peptide-folded SCNPs as drug delivery carriers in nanomedicine. Unlike larger self-assembled micelles and polymersomes, they can be folded in aqueous environment and can access cellular uptake mechanisms unavailable to larger particles. These results also highlight the value of FRET techniques in probing the complex behaviour of biocompatible SCNPs outside and inside of the cellular environment, which we hope will provide greater insight into the biological behaviour of this interesting new class of nanoparticles.

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Product Details of H-Gly-Gly-OH

CAS No. :556-50-3
Formula : C4H8N2O3
M.W : 132.12
SMILES Code : O=C(O)CNC(CN)=O
MDL No. :MFCD00008130
InChI Key :YMAWOPBAYDPSLA-UHFFFAOYSA-N
Pubchem ID :11163

Safety of H-Gly-Gly-OH

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H319
Precautionary Statements:P305+P351+P338

Application In Synthesis of H-Gly-Gly-OH

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 556-50-3 ]

[ 556-50-3 ] Synthesis Path-Downstream   1~4

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