Synthesis of cyclic Herpes simplex virus peptides containing 281-284 epitope of glycoprotein D-1 in endo- or exo-position

G. Mező, Zs. Majer, Mari Luz Valero, David Andreu, F. Hudecz

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

We have prepared two types of cyclopeptides containing the 281DPVG284 sequence from the 276-284 region of glycoprotein gD-1 of the Herpes simplex virus (HSV). The syntheses were performed by solid phase methodology using MBHA or BHA resin and orthogonal protection schemes. Head-to-side-chain cyclization included the N-terminal part of the epitope, while side-chain-to-side-chain lactam bridge formation resulted in a peptide containing a C-terminal cycle. Peptides elongated by Cys at the N-terminal of the sequence were also prepared. Boc chemistry using Fmoc and OFm orthogonal protection was applied for on-resin cyclization. Based on the orthogonality of Bzl and cHex esters under a 1 M TMSOTf-thioanisole/TFA cleavage condition, a new approach for the cyclization on BHA-resin has also been developed. Preliminary studies on solution conformation of the cyclic peptides by CD spectroscopy indicated the importance of the location and the size of the cycle within the epitope sequence.

Original languageEnglish
Pages (from-to)272-282
Number of pages11
JournalJournal of Peptide Science
Volume5
Issue number6
DOIs
Publication statusPublished - Jun 1999

Fingerprint

Cyclization
Simplexvirus
Viruses
Butylated Hydroxyanisole
Epitopes
Cyclic Peptides
Glycoproteins
Resins
Peptides
Lactams
Conformations
Spectrum Analysis
Esters
Head
Spectroscopy

Keywords

  • CD of cyclic peptides
  • Cyclic epitope peptides of Herpes simplex virus gD protein
  • Orthogonality of cyclohexyl and benzyl esters
  • Peptide cyclization on solid phase
  • TMSOTf cleavage

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry

Cite this

Synthesis of cyclic Herpes simplex virus peptides containing 281-284 epitope of glycoprotein D-1 in endo- or exo-position. / Mező, G.; Majer, Zs.; Valero, Mari Luz; Andreu, David; Hudecz, F.

In: Journal of Peptide Science, Vol. 5, No. 6, 06.1999, p. 272-282.

Research output: Contribution to journalArticle

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