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Occurrence of the d-Proline Chemotype in Enzyme Inhibitors

Department of Chemistry “Ugo Schiff”, University of Florence, Via della Lastruccia 13, Sesto Fiorentino, 50019 Florence, Italy
Interdepartmental Center for Preclinical Development of Molecular Imaging (CISPIM), University of Florence, Viale Morgagni 85, 50134 Florence, Italy
Author to whom correspondence should be addressed.
Symmetry 2019, 11(4), 558;
Received: 29 March 2019 / Revised: 15 April 2019 / Accepted: 17 April 2019 / Published: 18 April 2019
(This article belongs to the Special Issue Amino Acid Chirality)
PDF [3083 KB, uploaded 18 April 2019]


Natural and nonnatural amino acids represent important building blocks for the development of peptidomimetic scaffolds, especially for targeting proteolytic enzymes and for addressing protein–protein interactions. Among all the different amino acids derivatives, proline is particularly relevant in chemical biology and medicinal chemistry due to its secondary structure’s inducing and stabilizing properties. Also, the pyrrolidine ring is a conformationally constrained template that can direct appendages into specific clefts of the enzyme binding site. Thus, many papers have appeared in the literature focusing on the use of proline and its derivatives as scaffolds for medicinal chemistry applications. In this review paper, an insight into the different biological outcomes of d-proline and l-proline in enzyme inhibitors is presented, especially when associated with matrix metalloprotease and metallo-β-lactamase enzymes. View Full-Text
Keywords: drug discovery; amino acids; peptidomimetics; enzyme inhibitors; chiral pool; stereochemistry drug discovery; amino acids; peptidomimetics; enzyme inhibitors; chiral pool; stereochemistry

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Lenci, E.; Trabocchi, A. Occurrence of the d-Proline Chemotype in Enzyme Inhibitors. Symmetry 2019, 11, 558.

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