General synthesis of unsymmetrical norbornane scaffolds as inducers for hydrogen bond interactions in peptides.
Starting from readily accessible endo-cis-(2S,3R)-norbornene dicarboxylic acid benzyl monoester, a general and efficient synthetic approach toward unsymmetrical two-stranded peptidic structures was developed. In these structures the peptide strands are oriented in a parallel geometry. Their synthesis is easily applicable to a variety of amino acids and peptides. Specifically, a norbornane template as molecular scaffold induces hydrogen bonding between the adjacent peptide strands. The specific hydrogen bonding patterns between these strands were revealed by detailed NMR analysis including TOCSY/NOE experiments.
Hackenberger
Christian P R
CP
Institut für Organische Chemie der RWTH Aachen, Prof.-Pirlet-Str. 1, D-52056 Aachen, Germany.
Schiffers
Ingo
I
Runsink
Jan
J
Bolm
Carsten
C
D000596:Amino Acids / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009636:Norbornanes / Q000138:chemical synthesis / Q000737:chemistry*; D009842:Oligopeptides / Q000138:chemical synthesis / Q000737:chemistry*; D011487:Protein Conformation
D000596:Amino Acids; D004952:Esters; D009636:Norbornanes; D009842:Oligopeptides