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Peptide and Pseudopeptide Bond Synthesis in Phosphorus Dipeptide Analogs

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Peptide Synthesis

Part of the book series: Methods in Molecular Biology ((MIMB,volume 2103))

Abstract

Peptide analogs modified with a phosphorus-based moiety (phosphonate, phosphonamidate, or phosphinate) have emerged as invaluable tools in fundamental and medicinal, mechanistic, and inhibitory studies of proteolytic enzymes and other catalytic proteins that process the amino acids and peptides. The first stages of the chemical synthesis of these compounds frequently involve formation of peptide or pseudopeptide bond between a suitably protected α-amino acid and an α-aminoalkyl phosphorus derivative. These preparative protocols are distinct from conventional solution and solid-phase peptide syntheses that have become routine and automatized. In the following chapter, we describe in details the methods and techniques utilized to perform this nonstandard coupling and to obtain P-terminal dipeptidyl phosphonates and pseudodipeptides containing the internal phosphonamidate or phosphinate linkages. Methods of products’ purification, the deprotection conditions, and stability issues are also presented and discussed.

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Authors and Affiliations

  1. Department of Bioorganic Chemistry, Wrocław University of Science and Technology, Wrocław, Poland

    Artur Mucha & Paweł Kafarski

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  1. Artur Mucha
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  2. Paweł Kafarski
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Correspondence to Artur Mucha .

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Editors and Affiliations

  1. School of Chemistry and Molecular Biosciences, The University of Queensland, St. Lucia, QLD, Australia

    Waleed M. Hussein

  2. School of Chemistry and Molecular Biosciences, The University of Queensland, St. Lucia, QLD, Australia

    Mariusz Skwarczynski

  3. School of Chemistry and Molecular Biosciences, The University of Queensland, St. Lucia, QLD, Australia

    Istvan Toth

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Mucha, A., Kafarski, P. (2020). Peptide and Pseudopeptide Bond Synthesis in Phosphorus Dipeptide Analogs. In: Hussein, W., Skwarczynski, M., Toth, I. (eds) Peptide Synthesis. Methods in Molecular Biology, vol 2103. Humana, New York, NY. https://doi.org/10.1007/978-1-0716-0227-0_20

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  • DOI: https://doi.org/10.1007/978-1-0716-0227-0_20

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  • Publisher Name: Humana, New York, NY

  • Print ISBN: 978-1-0716-0226-3

  • Online ISBN: 978-1-0716-0227-0

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