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

Abstract

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

9 Figures and Tables

Statistics

0100200300201220132014201520162017
Citations per Year

190 Citations

Semantic Scholar estimates that this publication has 190 citations based on the available data.

See our FAQ for additional information.

Cite this paper

@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} }