Synthesis and structural characterization of bioactive peptide conjugates using thioether linkage approaches

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2004
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Mezö, Gábor
Jakab, Annamária
Kapuvári, Bence
Bösze, Szilvia
Schlosser, Gitta
Hudecz, Ferenc
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Journal of Peptide Science. 2004, 10(12), pp. 701-713. ISSN 1075-2617. Available under: doi: 10.1002/psc.583
Zusammenfassung

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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540 Chemie
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peptide conjugates, tetratuftsin derivative, thioether bond, Cys-peptides, HSV epitope peptide, β-amyloid epitope, GnRH-II
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ISO 690MEZÖ, 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.583
BibTex
@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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