Towards the synthesis of novel cyclopolypeptides by ring-closing metathesis Navneet Jhariya, Joëlle Prunet School of Chemistry, University of Glasgow, UK Polypeptides have gained a significantattention due to their extensive biomedical applications such as tissue engineering, drug delivery etc. 1,2 Collagen-like polypeptides offer versatile properties such as biocompatibility, biodegradability, bioactivities, and self-assembling capabilities. 1,3 The goal of this project is to synthesise novel cyclopolypeptides (CPP) by ring-closing metathesis (RCM). The corresponding CPP will be hydrogenated and self-assembly of this will be studied which may form a quaternary structure like the triple helix network found in collagen. 1,4,5 The L-allylglycine N-carboxy anhydride (LAGNCA) monomer (R = H) was engaged in ring-opening polymerisation1 to give poly(L-allylglycine) (PLAG) and the terminal olefin was isomerised to the internal one using Pd catalysis.6 Initial attempts of RCM4 did not lead to the desired CPP, the major issue being the insolubility of PLAG (R = H). To address the solubility issue, 2,4-dimethoxybenzyl protected LAGNCA (R = DMB) was synthesised, and ROP was performed that was unsuccessful. Thus, to verify the hypothesis a DMB-protected dipeptide was submitted to RCM, which showed conversion to the desired δ-lactam. 7 References 1. Sun, J.; Schlaad, H., Macromolecules 2010, 43, 4445-4448.
2. Zhang, P.; Li, M.; Xiao, C.; Chen, X., Chem. Commun. 2021, 57, 9489-9503. 3. Cai, C.; Lin, J.; Lu, Y.; Zhang, Q.; Wang, L., Chem. Soc. Rev. 2016, 45 , 5985-6012. 4. Alkattan, M.; Prunet, J.; Shaver, M. P., Angew. Chem. Int. Ed. 2018, 57, 12835-12839. 5. Kramer, J. R.; Deming, T. J., Polym. Chem. 2014, 5, 671-682. 6. Eckermann, R.; Breunig, M.; Gaich, T., Chem. Eur. J. 2017, 23, 3938-3949. 7. Creighton, C. J.; Leo, G. C.; Du, Y.; Reitz, A. B., Bioorg. Med. Chem. 2004, 12, 4375-4385.
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