Proline derived spirobarbiturates as highly effective beta-turn mimetics incorporating polar and functionalizable constraint elements.
A practical and efficient synthesis of spirobarbiturates of type III is reported when NH acidity of the imide function of the hydrophilic linker element allowed the introduction of different substituents. Structural characterization, which was based on both X-ray crystallography and spectroscopic investigations, indicated type II beta-turn formation. Introduction of the molecular scaffold into solid phase peptide synthesis gave rise to spirocyclic neuropeptide analogs.
Lomlim
Luelak
L
Department of Chemistry and Pharmacy, Emil Fischer Center, Friedrich Alexander University, Schuhstrasse 19, D-91052 Erlangen, Germany.
Einsiedel
Juergen
J
Heinemann
Frank W
FW
Meyer
Karsten
K
Gmeiner
Peter
P
D001463:Barbiturates / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D010880:Piperidines / Q000737:chemistry; D011392:Proline / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D001463:Barbiturates; D010880:Piperidines; D013141:Spiro Compounds; C032727:piperidine; D011392:Proline; C032232:barbituric acid