A New Example of Edge-to-Face Interaction of Aromatic Rings in Oligopeptides: Cyclolinopeptide A

Siemion, Ignacy Z.

doi:10.1515/znb-1990-0916

Cited by 8 publications

(1 citation statement)

References 4 publications

(4 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…An interesting feature of the CLA conformation is the reciprocal orientation of the aromatic rings of the two Phe residues. The rings are perpendicular to each other, forming an edge-to-face interaction [25]. The experiments with tyrosine analogues of CLA unequivocally showed that the residue in the position 4 plays a role of the 'edge' and the one in position 3 a role of the 'face' in this interaction.…”

Section: Structurementioning

confidence: 94%

Cyclopeptides ofLinum usitatissimum

et al. 2006

Self Cite

View full text Add to dashboard Cite

Cyclolinopeptide A (CLA), a cyclic nonapeptide from linseed, possesses strong immunosuppressive and antimalarial activity along with the ability to inhibit cholate uptake into hepatocytes. The structure of the peptide was studied extensively in solution as well as in the solid state. It is postulated that both the Pro-Pro cis-amide bond and an 'edge-to-face' interaction between the aromatic rings of two adjacent Phe residues are important for biological activity. Structure-activity relationship studies of many linear and cyclic analogues of CLA suggest that the Pro-Xxx-Phe sequence and the flexibility of the peptide are important for the immunosuppressive activity.

show abstract

Section: Structurementioning

confidence: 94%

Cyclopeptides ofLinum usitatissimum

et al. 2006

Self Cite

View full text Add to dashboard Cite

show abstract

Correlating biological activity with calculated geometric motifs in cyclolinopeptide A analogs

Zubrzak

Lepławy

Kowalski

et al. 2004

J of Physical Organic Chem

View full text Add to dashboard Cite

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.

show abstract