(Chemical Equation Presented) 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′ β-turn conformations.
Tetrahydroisoquinoline-Based Spirocyclic Lactam as a Type II’ β-Turn Inducing Peptide Mimetic / G. Lesma, N. Landoni, T. Pilati, A. Sacchetti, A. Silvani. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 74:21(2009), pp. 8098-8105. [10.1021/jo901480d]
Tetrahydroisoquinoline-Based Spirocyclic Lactam as a Type II’ β-Turn Inducing Peptide Mimetic
G. LesmaPrimo
;N. LandoniSecondo
;A. SilvaniUltimo
2009
Abstract
(Chemical Equation Presented) 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′ β-turn conformations.Pubblicazioni consigliate
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