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ChemistryOpen. 2020 Apr 03;9(4):431-441. doi: 10.1002/open.202000030. eCollection 2020 Apr.

Investigation of Parameters that Affect Resin Swelling in Green Solvents.

ChemistryOpen

Chidi Amadi-Kamalu, Holly Clarke, Matthew McRobie, James Mortimer, Michael North, Yanrui Ran, Anne Routledge, Dani Sibbald, Matthew Tickias, Kai Tse, Helen Willway

Affiliations

  1. Department of Chemistry University of York York UK YO10 5DD.

PMID: 32257751 PMCID: PMC7121665 DOI: 10.1002/open.202000030

Abstract

The influence of various physical and chemical factors on the swelling of polystyrene and PEG based resins in greener organic solvents has been systematically investigated. In general, chemical factors: the nature of the functionality/linker and the degree of loading were found to have a far larger influence on the swelling of the resins than physical parameters such as bead size. The results are interpreted in terms of Hansen solubility parameters for the solvents and there is evidence that some solvents interact with the polymeric core of a resin whilst others interact with the functionality. The results are extended to a study of the changes in resin swelling observed during both deprotection and chain elongation reactions during solid phase peptide synthesis.

© 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

Keywords: ChemMatrix; peptide; polystyrene; solvent; swelling

References

  1. Int J Pept Protein Res. 1992 Sep-Oct;40(3-4):208-13 - PubMed
  2. Chemistry. 2019 Apr 1;25(19):4951-4964 - PubMed
  3. Angew Chem Int Ed Engl. 2018 Oct 22;57(43):14286-14290 - PubMed
  4. J Am Chem Soc. 1973 Feb 21;95(4):1328-33 - PubMed
  5. Chemistry. 2001 Sep 17;7(18):3880-3 - PubMed
  6. J Org Chem. 2019 Apr 19;84(8):4615-4628 - PubMed
  7. J Comb Chem. 2006 Mar-Apr;8(2):213-20 - PubMed
  8. J Comb Chem. 2009 Mar 9;11(2):213-5 - PubMed
  9. J Comb Chem. 2001 Jan-Feb;3(1):9-15 - PubMed
  10. Bioorg Chem. 2011 Apr;39(2):101-9 - PubMed
  11. Chem Asian J. 2019 Apr 15;14(8):1088-1097 - PubMed
  12. Org Biomol Chem. 2019 Aug 14;17(30):7238-7246 - PubMed

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