PMID: 11606215Oct 19, 2001Paper

Synthesis, isolation and characterization of Plasmodium falciparum antigenic tetrabranched peptide dendrimers obtained by thiazolidine linkages

The Journal of Peptide Research : Official Journal of the American Peptide Society
F ChavesM E Patarroyo

Abstract

Different chemical alternatives were evaluated for obtaining immunogenic polypeptidic macromolecules which could then be used as vaccines. These were based on the ligation reaction between an unprotected immunogenic peptide and an unprotected multifunctional core peptide; polyantigens, designated dendrimers because their form resembles that of dendritic cells, were thus obtained. The antigen-core ligation alternatives, studied by indirect synthesis, were the formation of oxime, hydrazone and thiazolidine linkages, making use of the reaction between a weak base (acting as nucleophile) and an alkyl aldehyde. The other alternative was the formation of a thioether linkage between a sulfydryl and an alkyl halide. Finally, a multiple antigen peptide (MAP) was synthesized by direct synthesis. All reactions were monitored by SEC-HPLC and SDS-PAGE. Dendrimer molecular mass obtained was confirmed by MS MALDI-TOF. Dendrimer purification was first carried out by concentrating crude reaction products with CP-5000 centricons and (using SEC-HPLC) pure tetramers were then obtained. A 20-residue 9376 immunogenic sequence, from Plasmodium falciparum apical merozoite antigen protein (AMA-1), was used to study the best alternative for chemical lig...Continue Reading

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Citations

Dec 10, 2002·Current Opinion in Chemical Biology·Mary J Cloninger
Aug 28, 2012·BMC Infectious Diseases·Paola LassoConcepción Judith Puerta
Jan 1, 2012·Progress in Polymer Science·Daniel J SiegwartKrzysztof Matyjaszewski
Nov 26, 2009·Israel Journal of Chemistry·Wen ZhangEric E Simanek
May 17, 2003·Nature Reviews. Drug Discovery·Ruth Duncan
Oct 1, 2005·Journal of Peptide Science : an Official Publication of the European Peptide Society·Petr NiederhafnerJan Jezek
Mar 19, 2016·Angewandte Chemie·Jingjing Wan, Paul F Alewood
May 12, 2005·Chemical Reviews·Laia CrespoFernando Albericio
Sep 27, 2019·Chemical Reviews·Rachit SapraV Haridas
Mar 17, 2005·Bioconjugate Chemistry·Gueorgui MihovKlaus Müllen

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