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Correlating biological activity with calculated geometric motifs in cyclolinopeptide A analogs
Author(s) -
Zubrzak P.,
Leplawy M. T.,
Kowalski M. L.,
Szkudlińska B.,
Paneth P.,
Silberring J.,
Suder P.,
Zabrocki J.
Publication year - 2004
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.782
Subject(s) - chemistry , computational chemistry , stereochemistry
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 Phe 8 –Phe 9 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.