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Bypassing Osmotic Shock Dilemma in a Polystyrene Resin Using the Green Solvent Cyclopentyl methyl Ether (CPME): A Morphological Perspective

1
Peptide Science Laboratory, School of Chemistry and Physics, University of KwaZulu-Natal, Durban 4001, South Africa
2
KwaZulu-Natal Research Innovation and Sequencing Platform (KRISP), School of Laboratory Medicine and Medical Sciences, College of Health Sciences, University of KwaZulu-Natal, Durban 4041, South Africa
3
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
4
Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Alexandria 21321, Egypt
5
Purolite, Llantrisant Business Park, Llantrisant, CF72 8LF, UK
6
CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, University of Barcelona, 08028 Barcelona, Spain
7
Department of Organic Chemistry, University of Barcelona, 08028 Barcelona, Spain
*
Authors to whom correspondence should be addressed.
Polymers 2019, 11(5), 874; https://doi.org/10.3390/polym11050874
Received: 13 April 2019 / Revised: 2 May 2019 / Accepted: 11 May 2019 / Published: 13 May 2019
PDF [1542 KB, uploaded 13 May 2019]

Abstract

The “osmotic shock” phenomenon is the main thing that is responsible for morphological structure alteration, which can jeopardize the use of a polymer in a chemical process. This is extremely important in solid-phase peptide synthesis (SPPS), which is the method of choice for the preparation of these important biologically active compounds. Herein, we have used Hildebrand solubility parameters (δ) to investigate the influence of different ethers that are used in the precipitation step of the SPPS using a polystyrene resin. The green cyclopentyl methyl ether (CPME) has shown to be slightly superior to 2-methyltetrahydrofurane, which is also a green ether and clearly better than the hazardous diethyl ether and tert-butyl methyl ether. These results have been corroborated by scanning electron microscope (SEM) analysis and computational studies. All together, these confirm the adequacy of CPME for being the ether of choice to be used in SPPS.
Keywords: solid-phase peptide synthesis; osmotic shock; green solvent solid-phase peptide synthesis; osmotic shock; green solvent
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Al Musaimi, O.; El-Faham, A.; Almarhoon, Z.; Basso, A.; de la Torre, B.G.; Albericio, F. Bypassing Osmotic Shock Dilemma in a Polystyrene Resin Using the Green Solvent Cyclopentyl methyl Ether (CPME): A Morphological Perspective. Polymers 2019, 11, 874.

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