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Investigation of the automated solid-phase synthesis of a 38mer peptide with difficult sequence pattern under different synthesis strategies

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Abstract

Difficult peptides are a constant challenge in solid-phase peptide synthesis. In particular, hydroxyl amino acids such as serine can cause severe breakdowns in coupling yields even several amino acids after the insertion of the critical amino acid. This paper investigates several methods of improving synthesis yields of difficult peptides including the use of different resins, activators and the incorporation of a structure-breaking pseudoproline dipeptide building block both alone and in combination with each other.

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Acknowledgments

We thank Myriame S. Gabay, the former manager of the now closed Peptide Array Facility at the Brain Research Centre at the University of British Columbia (UBC), for her support of initial project work. D. W. also thanks Kuan Yu Nan, student at UBC, for his valuable general assistance while working at Kinexus. The authors thank Chris Meschino, UBC, for critical reading of the manuscript.

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The authors declare that they have no conflict of interest.

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Authors and Affiliations

  1. Peptide Facility, Kinexus Bioinformatics Corporation, 8755 Ash Street, Suite 1, Vancouver, BC, V6P 6T3, Canada

    Dirk F. H. Winkler & Kerry Tian

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  1. Dirk F. H. Winkler
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  2. Kerry Tian
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Correspondence to Dirk F. H. Winkler.

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Handling Editor: J. Bode.

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Winkler, D.F.H., Tian, K. Investigation of the automated solid-phase synthesis of a 38mer peptide with difficult sequence pattern under different synthesis strategies. Amino Acids 47, 787–794 (2015). https://doi.org/10.1007/s00726-014-1909-6

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  • DOI: https://doi.org/10.1007/s00726-014-1909-6

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