Synthesis of a Novel Tricyclic Dipeptide Template and Its Incorporation into a Cyclic Peptide Mimetic Containing an NPNA Motif

✍ Scribed by Marc E. Pfeifer; Anthony Linden; John A. Robinson

• Book ID: 102861469
• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: German
• Weight: 958 KB
• Volume: 80
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19970800514

✦ Synopsis

A novel tricyclic dipeptide template, formally derived by coupling (2S,4S)-4-aminoproline (Pro(NH,)) and (S)-2-(carboxymethyl)proline (Pro(CH,COOH)) as a diketopiperazine, has been synthesized in a form suitable for solid-phase peptide synthesis using Fmoc chemistry. This ternplate was incorporated into the cyclic molecule cyclo(-Ala'-AsnZ-Pro3-Asn4-Ala5-Ala6-Temp-) (Temp = temdplate), whose conformation in H,O was studied by NMR methods. Average solution structures derived by restrained simulated annealing point to a highly populated PI-turn within the Asn-Pro-Asn-Ala motif and also indicate which conformations are likely to be preferred by the template.