Tetrahydroisoquinoline-based spirocyclic lactam as a type II' beta-turn inducing peptide mimetic.


We present here spirocyclic lactam derivatives, embodying D-Phe and L-Ala amino acids as the central core and acting as tetrapeptide and hexapeptide mimetics. An efficient route for their synthesis is demonstrated by using the strategic combination of Seebach's self-reproduction of chirality chemistry and the Pictet-Spengler condensation as key steps. The conformational behavior of peptide mimetics was investigated by molecular modeling, X-ray crystallography, NMR (solvent and temperature dependence), IR spectroscopy, and circular dichroism. All data suggest very stable and highly predictable type II' beta-turn conformations.

DOI: 10.1021/jo901480d

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@article{Lesma2009TetrahydroisoquinolinebasedSL, title={Tetrahydroisoquinoline-based spirocyclic lactam as a type II' beta-turn inducing peptide mimetic.}, author={Giordano Lesma and Nicola Landoni and Tullio Pilati and Alessandro Sacchetti and Alessandra Silvani}, journal={The Journal of organic chemistry}, year={2009}, volume={74 21}, pages={8098-105} }