Premium
Synthesis of a Novel Tricyclic Dipeptide Template and Its Incorporation into a Cyclic Peptide Mimetic Containing an NPNA Motif
Author(s) -
Pfeifer Marc E.,
Linden Anthony,
Robinson John A.
Publication year - 1997
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19970800514
Subject(s) - chemistry , dipeptide , tricyclic , cyclic peptide , peptide , stereochemistry , template , peptide synthesis , solid phase synthesis , combinatorial chemistry , molecule , structural motif , proline , amino acid , nanotechnology , organic chemistry , biochemistry , materials science
A novel tricyclic dipeptide template, formally derived by coupling (2 S ,4 S )‐4‐aminoproline (Pro(NH 2 )) and ( S )‐2‐(carboxymethyl)proline (Pro(CH 2 COOH)) as a diketopiperazine, has been synthesized in a form suitable for solid‐phase peptide synthesis using Fmoc chemistry. This template was incorporated into the cyclic molecule cyclo(‐Ala 1 ‐Asn 2 ‐Pro 3 ‐Asn 4 ‐Ala 5 ‐Ala 6 ‐Temp‐) (Temp = template), whose conformation in H 2 O was studied by NMR methods. Average solution structures derived by restrained simulated annealing point to a highly populated βI‐turn within the Asn‐Pro‐Asn‐Ala motif and also indicate which conformations are likely to be preferred by the template.