title: Silicon-Containing Amino Acids: Synthetic Aspects, Conformational Studies, and Applications to Bioactive Peptides.
abstract: Unnatural α-amino acids form a family of essential molecules used for, among other applications, the synthesis of modified peptides, to improve resistance to proteolytic enzyme degradation, and to modulate physico- and biochemical properties of bioactive peptides as well as chiral inducers in asymmetric synthesis. Among them, silicon-containing unnatural amino acids are becoming an interesting new class of building blocks. The replacement of carbon atoms in bioactive substances with silicon is becoming increasingly popular. Peptides containing silyl amino acids hold great promise for maintaining or reinforcing the biological activity of active compounds, while they simultaneously enhance their resistance to enzyme degradation. In addition, the lipophilicity of the silicon atom facilitates their membrane crossing and their bioavailability. Nowadays, the interest of the pharmaceutical industry in peptide- and protein-based therapies is increasing. In this respect, silicon-containing amino acids and peptides are likely to be a significant part of future innovations in this area, and more generally in the area of biomolecules. In this process, commercial availability of silicon-containing amino acids is necessary: new syntheses have been developed, and work in this area is ongoing. This review aims to be a comprehensive and general summary of the different methods used to prepare silicon-containing amino acids and their implications on conformational structures and biological applications when they are incorporated into bioactive molecules.
authors.affiliation: Institut des Biomolécules Max Mousseron, Unité Mixte de Recherche 5247 de Centre National de la Recherche Scientifique, École Nationale Supérieure de Chimie de Montpellier, Université Montpellier , Place Eugène Bataillon, 34095 Montpellier Cedex 5, France.
authors.forename: Emmanuelle
authors.initials: E
authors.lastname: Rémond
authors.affiliation: Institut des Biomolécules Max Mousseron, Unité Mixte de Recherche 5247 de Centre National de la Recherche Scientifique, École Nationale Supérieure de Chimie de Montpellier, Université Montpellier , Place Eugène Bataillon, 34095 Montpellier Cedex 5, France.
authors.forename: Charlotte
authors.initials: C
authors.lastname: Martin
authors.affiliation: Institut des Biomolécules Max Mousseron, Unité Mixte de Recherche 5247 de Centre National de la Recherche Scientifique, École Nationale Supérieure de Chimie de Montpellier, Université Montpellier , Place Eugène Bataillon, 34095 Montpellier Cedex 5, France.
authors.forename: Jean
authors.initials: J
authors.lastname: Martinez
authors.affiliation: Institut des Biomolécules Max Mousseron, Unité Mixte de Recherche 5247 de Centre National de la Recherche Scientifique, École Nationale Supérieure de Chimie de Montpellier, Université Montpellier , Place Eugène Bataillon, 34095 Montpellier Cedex 5, France.
authors.forename: Florine
authors.initials: F
authors.lastname: Cavelier
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D008968:Molecular Conformation; D017646:Organosilicon Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010455:Peptides / Q000737:chemistry* / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000596:Amino Acids; D017646:Organosilicon Compounds; D010455:Peptides