Concerted synthesis of a spirobicyclic type-VI beta-turn mimic of Pro-Pro-Pro-NH2.
A highly concerted strategy for the synthesis of symmetrical type-VI beta-turn mimics was formulated. A proof of concept is presented in the synthesis of a spirobicyclic peptidomimetic of Pro-Pro-Pro-NH2, compound 6. The formation of an unusual adduct that was encountered in the process also is reported. This approach is potentially general for type-VI beta-turn mimics where the i+1 and i+2 residues are identical.
Department of Medicinal Chemistry, University of Minnesota, 308 Harvard Street SE, Minneapolis, Minnesota 55455, USA.
Ashish P
AP
Vartak
Rodney L
RL
Johnson
D000595:Amino Acid Sequence; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D018716:Molecular Mimicry; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D011487:Protein Conformation; D017433:Protein Structure, Secondary; D013141:Spiro Compounds / Q000737:chemistry*
D019086:Bridged Bicyclo Compounds, Heterocyclic; D009842:Oligopeptides; C514790:Pro-Pro-Pro-NH2; D013141:Spiro Compounds