Development of new amino(oxo)piperidinecarboxylate scaffolds and their evaluation as beta-turn mimics

Verbist, BMP; De Borggraeve, Wim; Toppet, Suzanne; Compernolle, Frans; Hoornaert, GJ

doi:10.1002/ejoc.200500036

Development of new amino(oxo)piperidinecarboxylate scaffolds and their evaluation as beta-turn mimics

Author:

Verbist, BMP

De Borggraeve, Wim ; Toppet, Suzanne ; Compernolle, Frans ; Hoornaert, GJ

Keywords:

intramolecular diels-alder reaction, 2(1h)-pyrazinones, beta-turn mimic, conformational-analysis, mimetics, peptides, position, design, bonds, Science & Technology, Physical Sciences, Chemistry, Organic, Chemistry, intramolecular Diels-Alder reaction, 2(1H)-pyrazinones, MIMETICS, DESIGN, 0304 Medicinal and Biomolecular Chemistry, 0305 Organic Chemistry, Organic Chemistry, 3404 Medicinal and biomolecular chemistry, 3405 Organic chemistry

Abstract:

In this paper a synthetic approach for functionalised bicyclic Amino(oxo)piperidinecarboxylate (APC) systems is presented. These systems can potentially be applied as cis-peptide bond containing beta-turn mimics. The scope and limitations of the synthetic method are discussed and the turn-inducing properties of a model compound are evaluated by means of molecular modelling and NMR analysis. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)