Clickable, Oxidation-Responsive and Enzyme-DegradablePolypeptide: Synthesis, Characterization and Side Chain Modification

Yan-Zhi Lu; An-Qi Gu; Tian-Lun Shen; Ji-Hong Sun; Jun Ling

doi:10.1007/s10118-022-2745-x

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Clickable, Oxidation-Responsive and Enzyme-DegradablePolypeptide: Synthesis, Characterization and Side Chain Modification

RESEARCH ARTICLE | Updated：2022-10-25

- Clickable, Oxidation-Responsive and Enzyme-DegradablePolypeptide: Synthesis, Characterization and Side Chain Modification
- Chinese Journal of Polymer Science Vol. 40, Issue 11, Pages: 1360-1368(2022)
- Affiliations：
  
  a.Ministry of Education Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027, China
  b.Department of Radiology, Sir Run Run Shaw Hospital, School of Medicine, Zhejiang University, Hangzhou 310016, China
- Author bio：
  
  lingjun@zju.edu.cn
- Funds：
- DOI：10.1007/s10118-022-2745-x
  CLC：
- Received：04 March 2022，
  
  Revised：2022-3-28，
  
  Accepted：29 March 2022，
  
  Online First：17 June 2022，
  
  Published：01 November 2022
- Accepted：
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Lu, Y. Z.; Gu, A. Q.; Shen, T. L.; Sun, J. H.; Ling, J. Clickable, oxidation-responsive and enzyme-degradable polypeptide: synthesis, characterization and side chain modification. Chinese J. Polym. Sci. 2022, 40, 1360–1368

Yan-Zhi Lu, An-Qi Gu, Tian-Lun Shen, et al. Clickable, Oxidation-Responsive and Enzyme-DegradablePolypeptide: Synthesis, Characterization and Side Chain Modification[J]. Chinese Journal of Polymer Science, 2022, 40(11): 1360-1368.
Lu, Y. Z.; Gu, A. Q.; Shen, T. L.; Sun, J. H.; Ling, J. Clickable, oxidation-responsive and enzyme-degradable polypeptide: synthesis, characterization and side chain modification. Chinese J. Polym. Sci. 2022, 40, 1360–1368 DOI： 10.1007/s10118-022-2745-x.

Yan-Zhi Lu, An-Qi Gu, Tian-Lun Shen, et al. Clickable, Oxidation-Responsive and Enzyme-DegradablePolypeptide: Synthesis, Characterization and Side Chain Modification[J]. Chinese Journal of Polymer Science, 2022, 40(11): 1360-1368. DOI： 10.1007/s10118-022-2745-x.

摘要

Poly(

-allylcysteine)

PAC

was synthesized via NCA and NPC. PAC can be modified by thiol-ene functionalization of pendent unsaturated bonds and oxidation of thioether to sulfoxide. Polyalliin

the oxidation product of PAC

are enzymatically degradable.

Abstract

Modifications at polypeptide side chains have been found to affect conformational and properties

which is a vital strategy to prepare functional polypeptides. This contribution describes the synthesis of homo and co-polypeptides containing unsaturated bonds and thioether moieties

poly(

-allylcysteine) (PAC). The pendant vinyl groups provide an active binding site which are able to be further modified with cysteine by thiol-ene click reaction. The sulfoxide from thioether oxidation bestows the polypeptide water solubility and enzymatic catalytic sites. The self-assembly micelles of PEG-

-PAC are ruptured along with oxidation to release the Nile red payloads. Moreover

poly(

-allyl-cysteine sulfoxide)

aka

. polyalliin

is the oxidation product of PAC which undergoes side chain cleavage catalyzed by alliinase enzyme. The polypeptides are biocompatible as confirmed by cell viability assays and may find applications in drug delivery

biosensing and nanoreactor.

关键词

Keywords

references

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