Design and synthesis of novel type VI-like β-turn mimetics. Diversity at the i+1 and the i+2 position

In this paper, a synthetic approach for functionalised 5-aminopiperidinone-2-carboxylate (APC) systems as non-pro cis-peptide bond containing external β-turn mimics is presented. The scope and limitations of the synthetic method are discussed and the potential turn inducing properties of a model com...

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Bibliographic Details
Published inTetrahedron Vol. 60; no. 50; pp. 11597 - 11612
Main Authors De Borggraeve, Wim M., Verbist, Bie M.P., Rombouts, Frederik J.R., Pawar, Vijaykumar G., Smets, Wim J., Kamoune, Laila, Alen, Jo, Van der Eycken, Erik V., Compernolle, Frans, Hoornaert, Georges J.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 06.12.2004
Elsevier
Subjects
Chemistry
Chemistry, Organic
Diels–Alder reaction
Physical Sciences
Pyrazinone
Science & Technology
Turn mimics
Diels–Alder reaction
Turn mimics
Pyrazinone
PEPTIDE-BONDS
DIELS-ALDER REACTIONS
turn mimics
POLYPEPTIDES
STABILIZE SECONDARY STRUCTURES
GLY-PRO
AMINO-ACIDS
pyrazinone
2(1H)-PYRAZINONES
GENERATION
Diels-Alder reaction
CONFORMATIONAL-ANALYSIS
DERIVATIVES
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Summary:In this paper, a synthetic approach for functionalised 5-aminopiperidinone-2-carboxylate (APC) systems as non-pro cis-peptide bond containing external β-turn mimics is presented. The scope and limitations of the synthetic method are discussed and the potential turn inducing properties of a model compound are evaluated by means of molecular modelling and NMR analysis. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.09.054