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Polyethyleneglycol-Based Resins as Solid Supports for the Synthesis of Difficult or Long Peptides

  • Bruce Merrifield Commemorative Issue
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International Journal of Peptide Research and Therapeutics Aims and scope Submit manuscript

An evaluation of the polyethyleneglycol-based ChemMatrix® resin as solid support for the synthesis of challenging peptide sequences is presented. Comparison with conventional polystyrene and polyethyleneglycol-polystyrene resins in several instances of typically difficult solid phase syntheses shows a consistently better performance of the ChemMatrix® resin in terms of end product purity. Representative test sequences include a 15-residue antibiotic, a gp41 ectodomain hybrid sequence, a calcipressin fragment with an N-terminal Arg11 extension, and two chemokines of 69- and 64-amino acid residues. Interestingly, a difference in only five amino-acids between the two chemokine sequences had a remarkable impact on synthetic results, which in the case of the 69-residue peptide required additional refinements (β-sheet-breaking pseudoproline dipeptides) for success.

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Acknowledgments

Work supported by grants PI040885 (Fondo Investigaciones Sanitarias, Spain), BIO2005-07592-CO20-02 (Ministerio de Educación y Ciencia, Spain) and SGR00494 (Generalitat de Catalunya, Spain).

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Authors and Affiliations

  1. Proteomics and Protein Chemistry Unit, Department of Experimental and Health Sciences, Pompeu Fabra University, Dr. Aiguader 80, Barcelona, 08003, Spain

    Beatriz G. de la Torre, Annamaria Jakab & David Andreu

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  1. Beatriz G. de la Torre
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  2. Annamaria Jakab
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  3. David Andreu
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Correspondence to David Andreu.

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This paper is dedicated to the memory of Bruce Merrifield, a dear teacher, mentor and friend.

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de la Torre, B.G., Jakab, A. & Andreu, D. Polyethyleneglycol-Based Resins as Solid Supports for the Synthesis of Difficult or Long Peptides. Int J Pept Res Ther 13, 265–270 (2007). https://doi.org/10.1007/s10989-006-9077-5

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  • DOI: https://doi.org/10.1007/s10989-006-9077-5

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