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Bifunctional Peptide–Polymer Conjugate-Based Fibers via a One-Pot Tandem Disulfide Reduction Coupled to a Thio-Bromo “Click” Reaction
[Image: see text] 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-bro...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2020
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7408259/ https://www.ncbi.nlm.nih.gov/pubmed/32775904 http://dx.doi.org/10.1021/acsomega.0c02326 |
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author | Kumar, Sonu Hause, Gerd Binder, Wolfgang H. |
author_facet | Kumar, Sonu Hause, Gerd Binder, Wolfgang H. |
author_sort | Kumar, Sonu |
collection | PubMed |
description | [Image: see text] 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) (M(n,GPC) = 8700 g mol(–1), Đ = 2.02) is reported to readily prepare the bi-headed conjugate FFFF-PEG-FFFF (M(n,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. |
format | Online Article Text |
id | pubmed-7408259 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-74082592020-08-07 Bifunctional Peptide–Polymer Conjugate-Based Fibers via a One-Pot Tandem Disulfide Reduction Coupled to a Thio-Bromo “Click” Reaction Kumar, Sonu Hause, Gerd Binder, Wolfgang H. ACS Omega [Image: see text] 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) (M(n,GPC) = 8700 g mol(–1), Đ = 2.02) is reported to readily prepare the bi-headed conjugate FFFF-PEG-FFFF (M(n,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. American Chemical Society 2020-07-23 /pmc/articles/PMC7408259/ /pubmed/32775904 http://dx.doi.org/10.1021/acsomega.0c02326 Text en Copyright © 2020 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
spellingShingle | Kumar, Sonu Hause, Gerd Binder, Wolfgang H. Bifunctional Peptide–Polymer Conjugate-Based Fibers via a One-Pot Tandem Disulfide Reduction Coupled to a Thio-Bromo “Click” Reaction |
title | Bifunctional Peptide–Polymer Conjugate-Based
Fibers via a One-Pot Tandem Disulfide Reduction Coupled to a Thio-Bromo
“Click” Reaction |
title_full | Bifunctional Peptide–Polymer Conjugate-Based
Fibers via a One-Pot Tandem Disulfide Reduction Coupled to a Thio-Bromo
“Click” Reaction |
title_fullStr | Bifunctional Peptide–Polymer Conjugate-Based
Fibers via a One-Pot Tandem Disulfide Reduction Coupled to a Thio-Bromo
“Click” Reaction |
title_full_unstemmed | Bifunctional Peptide–Polymer Conjugate-Based
Fibers via a One-Pot Tandem Disulfide Reduction Coupled to a Thio-Bromo
“Click” Reaction |
title_short | Bifunctional Peptide–Polymer Conjugate-Based
Fibers via a One-Pot Tandem Disulfide Reduction Coupled to a Thio-Bromo
“Click” Reaction |
title_sort | bifunctional peptide–polymer conjugate-based
fibers via a one-pot tandem disulfide reduction coupled to a thio-bromo
“click” reaction |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7408259/ https://www.ncbi.nlm.nih.gov/pubmed/32775904 http://dx.doi.org/10.1021/acsomega.0c02326 |
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