title: Synthesis and modifications of phosphinic dipeptide analogues.
abstract: Pseudopeptides containing the phosphinate moiety (-P(O)(OH)CH(2)-) have been studied extensively, mainly as transition state analogue inhibitors of metalloproteases. The key synthetic aspect of their chemistry is construction of phosphinic dipeptide derivatives bearing appropriate side-chain substituents. Typically, this synthesis involves a multistep preparation of two individual building blocks, which are combined in the final step. As this methodology does not allow simple variation of the side-chain structure, many efforts have been dedicated to the development of alternative approaches. Recent achievements in this field are summarized in this review. Improved methods for the formation of the phosphinic peptide backbone, including stereoselective and multicomponent reactions, are presented. Parallel modifications leading to the structurally diversified substituents are also described. Finally, selected examples of the biomedical applications of the title compounds are given.
authors.affiliation: Department of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland. artur.mucha@pwr.wroc.pl
authors.forename: Artur
authors.initials: A
authors.lastname: Mucha
mesh_terms: D000179:Acrylates / Q000737:chemistry; D000478:Alkylation; D000818:Animals; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D006801:Humans; D006868:Hydrolysis; D010721:Phosphinic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D060327:Solid-Phase Synthesis Techniques
chemical_list: D000179:Acrylates; D004151:Dipeptides; D010721:Phosphinic Acids