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Pyridyl disulfide reaction chemistry : an efficient strategy toward redox-responsive cyclic peptide–polymer conjugates
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Song, Qiao, Yang, Jie, Hall, Stephen C. L., Gurnani, Pratik and Perrier, Sébastien (2019) Pyridyl disulfide reaction chemistry : an efficient strategy toward redox-responsive cyclic peptide–polymer conjugates. ACS Macro Letters, 8 (10). pp. 1347-1352. doi:10.1021/acsmacrolett.9b00538 ISSN 2161-1653.
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WRAP-Pyridyl-disulfide-chemistry-strategy-redox-cyclic-Song-2019.pdf - Accepted Version - Requires a PDF viewer. Download (1585Kb) | Preview |
Official URL: https://doi.org/10.1021/acsmacrolett.9b00538
Abstract
Cyclic peptide–polymer conjugates are capable of self-assembling into supramolecular polymeric nanotubes driven by the strong multiple hydrogen bonding interactions between the cyclic peptides. In this study, we have engineered responsive nanotubes by introducing a cleavable bond that responds to a reductant utilizing pyridyl disulfide reaction chemistry. Reactions between a cysteine containing cyclic peptide (CP-SH) and pyridyl disulfide containing polymers were initially studied, leading to the quantitative formation of cyclic peptide–polymer conjugates. An asymmetric cyclic peptide–polymer conjugate (PEG-CP-S-S-pPEGA) was then synthesized via orthogonal pyridyl disulfide reaction chemistry and NHS coupling chemistry. The disulfide linker formed by the pyridyl disulfide reaction chemistry was then selectively reduced to thiols in the presence of a reductant, enabling the transition of the conjugates from nonassembling unimers to self-assembled supramolecular polymeric nanotubes. It is anticipated that the pyridyl disulfide reaction chemistry will not only enrich the methodology toward the synthesis of cyclic peptide–polymer conjugates, but also lead to the construction of a new family of redox-responsive cyclic peptide–polymer conjugates and supramolecular polymeric nanotubes with tailored structures and functionalities.
| Item Type: | Journal Article | ||||||||||||||||||||||||
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| Subjects: | Q Science > QC Physics Q Science > QD Chemistry Q Science > QP Physiology T Technology > TA Engineering (General). Civil engineering (General) |
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| Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry Faculty of Science, Engineering and Medicine > Medicine > Warwick Medical School |
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| SWORD Depositor: | Library Publications Router | ||||||||||||||||||||||||
| Library of Congress Subject Headings (LCSH): | Cyclic peptides , Nanotubes, Conjugated polymers, Polymers, Polymeric composites | ||||||||||||||||||||||||
| Journal or Publication Title: | ACS Macro Letters | ||||||||||||||||||||||||
| Publisher: | American Chemical Society | ||||||||||||||||||||||||
| ISSN: | 2161-1653 | ||||||||||||||||||||||||
| Official Date: | 1 October 2019 | ||||||||||||||||||||||||
| Dates: |
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| Volume: | 8 | ||||||||||||||||||||||||
| Number: | 10 | ||||||||||||||||||||||||
| Page Range: | pp. 1347-1352 | ||||||||||||||||||||||||
| DOI: | 10.1021/acsmacrolett.9b00538 | ||||||||||||||||||||||||
| Status: | Peer Reviewed | ||||||||||||||||||||||||
| Publication Status: | Published | ||||||||||||||||||||||||
| Reuse Statement (publisher, data, author rights): | “This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Macro Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [insert ACS Articles on Request author-directed link to Published Work, see http://pubs.acs.org/page/policy/articlesonrequest/index.html].” | ||||||||||||||||||||||||
| Access rights to Published version: | Restricted or Subscription Access | ||||||||||||||||||||||||
| Date of first compliant deposit: | 2 December 2019 | ||||||||||||||||||||||||
| Date of first compliant Open Access: | 27 September 2020 | ||||||||||||||||||||||||
| RIOXX Funder/Project Grant: |
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