Effect of conjugation with polypeptide carrier on the enzymatic degradation of herpes simplex virus glycoprotein D derived epitope peptide

Regina Tugyi, G. Mező, G. Schlosser, Erzsébet Fellinger, David Andreu, F. Hudecz

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Two conjugates with epitope peptide 278LLEDPVGTVA287 derived from glycoprotein D (gD-1) of Herpes simplex virus (HSV) were synthesized for analysis of the effect of conjugation on protection against enzymatic degradation. In this design, the turn-forming epitope core 281DPVG284 was positioned in the central part of the peptide and elongated by three amino acids from the native sequence at both termini. Conjugation was achieved by the introduction of amide bond or thioether linkage between the C-terminal of the HSV peptide and the side chain of four lysine residues of the oligotuftsin derivative used as carrier molecule. We compared the proteolytic stability of the conjugates in diluted human sera as well as in rat liver lysosomal preparation. The data obtained in lysosomal preparation at two pH values (pH 3.5 and 5.0) show that the type of covalent bond between the carrier and the epitope peptide had no significant effect, as compared to the stability of the free, unconjugated peptide. Based on the identification of degradation fragments by mass spectrometry we found marked differences in the lengths and amounts of oligopeptides obtained. In contrast, in 10% and 50% human serum the conjugation provided full protection against enzymatic hydrolysis over 96 h, while the free peptide was decomposed quickly.

Original languageEnglish
Pages (from-to)1652-1659
Number of pages8
JournalBioconjugate Chemistry
Volume19
Issue number8
DOIs
Publication statusPublished - Aug 2008

Fingerprint

Epitopes
Glycoproteins
Polypeptides
Simplexvirus
Viruses
Peptides
Degradation
Oligopeptides
Enzymatic hydrolysis
Covalent bonds
Sulfides
Serum
Amides
Liver
Lysine
Mass spectrometry
Amino acids
Rats
Amino Acid Sequence
Mass Spectrometry

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Clinical Biochemistry
  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry

Cite this

Effect of conjugation with polypeptide carrier on the enzymatic degradation of herpes simplex virus glycoprotein D derived epitope peptide. / Tugyi, Regina; Mező, G.; Schlosser, G.; Fellinger, Erzsébet; Andreu, David; Hudecz, F.

In: Bioconjugate Chemistry, Vol. 19, No. 8, 08.2008, p. 1652-1659.

Research output: Contribution to journalArticle

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