Bifunctional Peptide–Polymer Conjugate-BasedFibers via a One-Pot Tandem Disulfide Reduction Coupled to a Thio-Bromo“Click” Reaction
2020
In
view of the potential applications of fibers in material sciences
and biomedicine, an effective synthetic strategy is described to construct
peptide-based bifunctional polymeric conjugates for supramolecular
self-association in solution. A direct coupling method of an α-acyl-brominated
peptide Phe-Phe-Phe-Phe (FFFF) with a disulfide-bridged polymeric
scaffold of poly(ethylene glycol) (PEG) (Mn,GPC = 8700 g mol–1, Đ = 2.02)
is reported to readily prepare the bi-headed conjugate FFFF-PEG-FFFF
(Mn,GPC = 3800 g mol–1, Đ = 1.10) via a one-pot, tandem disulfide
reduction (based on tris(2-carboxyethyl)phosphine hydrochloride (TCEP))
coupled to a thio-bromo “click” reaction. The conjugate
was investigated via transmission electron microscopy to exploit supramolecular
fibril formation and solvent-dependent structuring into macroscale
fibers via fibril–fibril interactions and interfibril cross-linking-induced
bundling. Circular dichroism spectroscopic analysis is further performed
to investigate β-sheet motifs in such fibrous scaffolds. Overall,
this synthetic approach opens an attractive approach for a simplified
synthesis of PEG-containing peptide conjugates.
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