Original Article:
Poly(ε-caprolactone) with pendant natural peptides: an old polymeric biomaterial with new properties
Yuanyuan Ju, et al.
Polym. Chem., 2017,8, 5415-5426
10.1039/C7PY01012E
Biofunctionalization of poly(ε-caprolactone) (PεCL) provides an avenue to broaden the applications of polymers in medicine and bioengineering. In this research, PεCL with pendant glutathione (GSH) or L-carnosine was synthesized by a combination of ring-opening copolymerization, Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction (click reaction) and thiol-disulfide exchange reaction.
The synthetic route of poly(εcaprolactone) (PεCL) with pyridyl disulfide pendant groups is shown in Figure (a). The schematic diagram of the synthesis of PεCL with pendant glutathione/L-carnosine molecules via thiol-disulfide exchange reaction is shown in panel (b).
Pyridine dithioethylamine works in two key steps: (1) Pyridyl disulfide groups were grafted to the backbones of PεCL through a reaction between the pendant NHS-activated ester and pyridine dithioethylamine. (2) The peptide modification of PεCL was achieved through the thiol-disulfide exchange reaction between the side chain disulfide groups on the polymer chain and the thiol groups on GSH (or L-carnosine-SH).
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Chemicals Related in the Paper:
| Catalog Number | Product Name | Structure | CAS Number | Price |
|---|---|---|---|---|
| ACM106139155 | Pyridine dithioethylamine hydrochloride(pda-hcl) |  |
106139-15-5 | Price |
