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Gelating polypeptide matrices based on the difunctional N-carboxyanhydride diaminopimelic acid cross-linker

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posted on 26.04.2021, 16:14 by Robert MurphyRobert Murphy, Elena Bobbi, Fernando CS de Oliveira, Sally-Ann CryanSally-Ann Cryan, Andreas HeiseAndreas Heise
This work reports the synthesis of a new difunctional N‐carboxyanhydride (NCA) monomer, namely diaminopimelic acid (DAP), and its use in the one‐pot preparation of an organogelating copolypeptide. The organogel is formed in situ through ring‐opening polymerization (ROP) of DAP NCA from helical poly(ε‐carbobenzyloxy‐L‐lysine) (PZLL) blocks in a mixture of dimethylformamide/chloroform. Gelation occurs by immobilizing the solvent through core crosslinking and is stabilized through physical intermolecular conformations. After removal of the carbobenzyloxy (cbz or Z) protecting groups, the network remains intact in exceedingly high aqueous concentrations (99.5%). FTIR is used to characterize the secondary structure, revealing the conformational arrangements that contributed to these stabilized gel networks with their relative mechanical properties determined via real‐time rheological assays. DAP core crosslink of the random coil forming polypeptoid poly(sarcosine) (PSar) is also resulting in networks but is devoid of any stabilized physical interactions, thus yielding significantly weaker gels as a result.

Funding

Science Foundation Ireland (SFI) Principle Investigator Award 13/IA/1840(T)

Brazilian Government-CAPES Grant Number No. 13695/2013-04.

History

Comments

This is the peer reviewed version of the following article:, Murphy RD, Bobbi E, de Oliveira FCS, Cryan, SA, Heise A. Gelating polypeptide matrices based on the difunctional N‐carboxyanhydride diaminopimelic acid cross‐linker. Journal of Polymer Science Part A: Polymer Chemistry. 2019;57(11):1209-1215, which has been published in final form at https://doi.org/10.1002/pola.29376. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.

Published Citation

Murphy RD, Bobbi E, de Oliveira FCS, Cryan, SA, Heise A. Gelating polypeptide matrices based on the difunctional N‐carboxyanhydride diaminopimelic acid cross‐linker. Journal of Polymer Science Part A: Polymer Chemistry. 2019;57(11):1209-1215.

Publication Date

4 April 2019

Department/Unit

  • Amber (Advanced Material & Bioengineering Research) Centre
  • Chemistry
  • Cu00daRAM Centre for Research in Medical Devices
  • School of Pharmacy and Biomolecular Sciences

Research Area

  • Respiratory Medicine
  • Chemistry and Pharmaceutical Sciences
  • Biomaterials and Regenerative Medicine

Publisher

Wiley

Version

  • Accepted Version (Postprint)