Enantio- and diastereoselective syntheses of cyclic Calpha-tetrasubstituted alpha-amino acids and their use to induce stable conformations in short peptides.
C(alpha)-tetrasubstituted alpha-amino acids are widely used to design and prepare peptides and peptide mimics with constrained conformations. Subcategories of these compounds are cyclic C(alpha)-tetrasubstituted alpha-amino acids, in which both alpha-substituents are covalently connected. This survey presents recent advances in the synthesis and application of cyclic C(alpha)-tetrasubstituted alpha-amino acids in a systematic order beginning with cyclopropane amino acids, continuing with four, five, six membered rings, and ring structures larger than six-membered. We discuss synthetic routes to the cyclic C(alpha)-tetrasubstituted alpha-amino acids and their use as conformation determining elements in peptides.
Maity
Prantik
P
Institut für Organische Chemie, Universität Regensburg, D-93040 Regensburg, Germany.
König
Burkhard
B
D000598:Amino Acids, Cyclic / Q000138:chemical synthesis / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D003515:Cycloleucine / Q000737:chemistry; D003521:Cyclopropanes / Q000737:chemistry; D009842:Oligopeptides / Q000737:chemistry*; D017433:Protein Structure, Secondary; D013237:Stereoisomerism
D000598:Amino Acids, Cyclic; D002264:Carboxylic Acids; D003521:Cyclopropanes; D009842:Oligopeptides; D003515:Cycloleucine; C030797:cyclopropane