Publikation: Synthesis and structural characterization of bioactive peptide conjugates using thioether linkage approaches
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Applications of cysteine-insertion and thioether linkage approaches to the preparation of a number of bioactive peptide conjugates are reported. Peptides containing epitopes from (i) herpes simplex virus type 1 glycoprotein D, (ii) a specific N-terminal beta-amyloid epitope recognized by therapeutically active antibodies, and (iii) a GnRH-III peptide from sea lamprey with antitumour activity, were elongated with Cys residues and attached to a chloroacetylated tetratuftsin derivative carrier via a thioether linkage either directly, or by insertion of a spacer. The structures and molecular homogeneity of all the peptide conjugates were ascertained by HPLC, MALDI and electrospray mass spectrometry. The use of a spacer such as an oligoglycine or GFLG-tetrapeptide gave an increased yield in the conjugation reaction and enhanced reaction rates. In the formation of cysteinyl-thioether linkages, it was found that the position of flanking Cys residues markedly influenced the conjugation reaction and the formation of intermolecular epitope disulfide-dimers. C-terminal Cys residues gave thioether conjugates with significantly diminished epitope-dimerization, while Cys at the N-terminal caused rapid disulfide-dimerization, thereby preventing efficient conjugation.
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MEZÖ, Gábor, Marilena MANEA, Annamária JAKAB, Bence KAPUVÁRI, Szilvia BÖSZE, Gitta SCHLOSSER, Michael PRZYBYLSKI, Ferenc HUDECZ, 2004. Synthesis and structural characterization of bioactive peptide conjugates using thioether linkage approaches. In: Journal of Peptide Science. 2004, 10(12), pp. 701-713. ISSN 1075-2617. Available under: doi: 10.1002/psc.583BibTex
@article{Mezo2004-12Synth-17580, year={2004}, doi={10.1002/psc.583}, title={Synthesis and structural characterization of bioactive peptide conjugates using thioether linkage approaches}, number={12}, volume={10}, issn={1075-2617}, journal={Journal of Peptide Science}, pages={701--713}, author={Mezö, Gábor and Manea, Marilena and Jakab, Annamária and Kapuvári, Bence and Bösze, Szilvia and Schlosser, Gitta and Przybylski, Michael and Hudecz, Ferenc} }
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