Sulfonated analogues of cyclolinopeptide A: Synthesis, immunosuppressive activity and CD studies

Marek Cebrat, Marek Lisowski, Ignacy Z. Siemion, Michał Zimecki, Zbigniew Wieczorek

Research output: Contribution to journalArticle

Abstract

Linear and cyclic analogues of cyclolinopeptide A (CLA) in which one or both phenylalanine residues in fragment Pro6-Pro7-Phe8-Phe9 were substituted by their sulfonated derivatives have been synthesized by SPPS method and cyclization with the BOP reagent. The peptides were examined for their immunosuppressive activity in the humoral and cellular immune response by PFC and DTH tests. All of the analogues retain some immunosuppressive activity of native CLA. Their CD spectra confirm that the optical activity of aromatic residues in CLA depends on their position in the peptide chain. Only the residue in position 8 seems to be optically active. CD spectrum of the cyclic analogue modified in position 9 is very similar to that of native CLA which correlates with its high biological activity. The chiroptical properties of the p-sulfonated Phe-residue are established.

Original languageEnglish (US)
Pages (from-to)415-420
Number of pages6
JournalJournal of Peptide Research
Volume49
Issue number5
Publication statusPublished - 1997
Externally publishedYes

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Keywords

  • Circular dichroism of peptides
  • Cyclolinopeptide A
  • Immunosuppression
  • Sulfonated phenylalanine

ASJC Scopus subject areas

  • Biochemistry
  • Endocrinology

Cite this

Cebrat, M., Lisowski, M., Siemion, I. Z., Zimecki, M., & Wieczorek, Z. (1997). Sulfonated analogues of cyclolinopeptide A: Synthesis, immunosuppressive activity and CD studies. Journal of Peptide Research, 49(5), 415-420.