title: The Use of Microwave-Assisted Solid-Phase Peptide Synthesis and Click Chemistry for the Synthesis of Vaccine Candidates Against Hookworm Infection.
abstract: A protein-based vaccine approach against hookworm infection has failed to deliver the expected outcome, due to a problem with an allergic response in the patient or difficulties in the proteins' production. This implication could be overcome by using a chemically synthesized peptide-based vaccine approach. This approach utilizes minimal pathogenic components that are necessary for the stimulation of the immune response without triggering adverse side effects. To boost the peptide's immunogenicity, a lipid core peptide (LCP) system can be utilized as a carrier molecule/immunostimulant. This chapter describes in detail the synthesizing of protected lipoamino acid, the self-adjuvanting moiety (LCP core), the peptide epitope, and the final vaccine candidate. The subunit peptide and the LCP core were synthesized using microwave-assisted solid-phase peptide synthesis (SPPS). Then the final hookworm vaccine construct was assembled using the copper-catalyzed azide-alkyne cycloaddition, or "click," reaction.
authors.affiliation: School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, St Lucia, QLD, 4072, Australia.
authors.forename: Abdullah A H Ahmad
authors.initials: AA
authors.lastname: Fuaad
authors.affiliation: School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, St Lucia, QLD, 4072, Australia. m.skwarczynski@uq.edu.au.
authors.forename: Mariusz
authors.initials: M
authors.lastname: Skwarczynski
authors.affiliation: School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, St Lucia, QLD, 4072, Australia.|School of Pharmacy, The University of Queensland, Woolloongabba, QLD, 4102, Australia.
authors.forename: Istvan
authors.initials: I
authors.lastname: Toth
mesh_terms: D000818:Animals; D057930:Click Chemistry / Q000379:methods*; D000939:Epitopes / Q000276:immunology; D006725:Hookworm Infections / Q000517:prevention & control*; D008872:Microwaves; D017221:Necator americanus / Q000276:immunology; D019308:Palmitic Acid / Q000737:chemistry; D060327:Solid-Phase Synthesis Techniques / Q000379:methods*; D014612:Vaccines / Q000138:chemical synthesis* / Q000737:chemistry / Q000276:immunology; D022223:Vaccines, Subunit / Q000138:chemical synthesis / Q000737:chemistry / Q000276:immunology
chemical_list: D000939:Epitopes; D014612:Vaccines; D022223:Vaccines, Subunit; D019308:Palmitic Acid
keywords: Click chemistry; Copper-catalyzed azide-alkyne cycloaddition; Fmoc-solid-phase peptide synthesis; Hookworm; Microwave-assisted solid-phase peptide synthesis; Peptide-based vaccine; Synthetic vaccine