Correlating biological activity with calculated geometric motifs in cyclolinopeptide A analogs

• Published in: Journal of physical organic chemistry Vol. 17; no. 6-7; pp. 625 - 630
• Main Authors: Zubrzak, P., Leplawy, M. T., Kowalski, M. L., Szkudlińska, B., Paneth, P., Silberring, J., Suder, P., Zabrocki, J.
• Format: Journal Article
• Language: English
• Published: Chichester, UK John Wiley & Sons, Ltd 01.06.2004
• Subjects: biological activity; cyclolinopeptide A; geometric motifs; molecular modeling
• ISSN: 0894-3230; 1099-1395
• DOI: 10.1002/poc.782

Three linear and three cyclic analogs of cyclolinopeptide A, with phenylalanine residues in position 8 and/or 9 replaced by N‐benzylglycine, were synthesized using the SPPS method and cyclization with TBTU reagent. The peptides were examined for their immunosuppressive activity in a lymphocyte proliferation test. In order to test the importance of the edge‐to‐face interactions between Phe8–Phe9 aromatic rings, molecular modeling studies were carried out. The results support its importance of the edge‐to‐face interactions for the biological activity of these compounds and indicate that the distance between the two rings also plays an essential role. Copyright © 2004 John Wiley & Sons, Ltd.