An Isodipeptide Building Block for Microwave-Assisted Solid-Phase Synthesis of Difficult Sequence-Containing Peptides

Waleed M Hussein; Mariusz Skwarczynski; Istvan Toth

doi:10.1007/978-1-0716-0227-0_9

An Isodipeptide Building Block for Microwave-Assisted Solid-Phase Synthesis of Difficult Sequence-Containing Peptides

Methods Mol Biol. 2020:2103:139-150. doi: 10.1007/978-1-0716-0227-0_9.

Authors

Waleed M Hussein¹, Mariusz Skwarczynski¹, Istvan Toth^{2

3

4}

Affiliations

¹ School of Chemistry and Molecular Biosciences, The University of Queensland, St. Lucia, QLD, Australia.
² School of Chemistry and Molecular Biosciences, The University of Queensland, St. Lucia, QLD, Australia. [email protected].
³ Institute for Molecular Bioscience, The University of Queensland, St Lucia, QLD, Australia. [email protected].
⁴ School of Pharmacy, The University of Queensland, Woolloongabba, QLD, Australia. [email protected].

PMID: 31879923
DOI: 10.1007/978-1-0716-0227-0_9

Abstract

Microwave technology, in conjunction with the isopeptide strategy including Fmoc-based solid-phase peptide synthesis (SPPS), was used to establish a methodology for time-efficient synthesis of peptides containing difficult sequences. A model difficult sequence-containing peptide (8Q_Ser) was synthesized through this method in 1 day, representing a tenfold reduction in synthesis time compared to the isopeptide method combined with classical SPPS.

Keywords: Depsipeptide; Difficult sequence; Isodipeptide unit; Microwave; O-N acyl migration; Solid-phase peptide synthesis.

MeSH terms

Amino Acids / chemistry*
Chemistry Techniques, Synthetic
Microwaves*
Molecular Structure
Peptide Fragments / chemical synthesis*
Peptide Fragments / chemistry
Peptide Fragments / isolation & purification
Solid-Phase Synthesis Techniques / methods*

Substances

Amino Acids
Peptide Fragments