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Molecules 2012, 17(11), 13530-13568; doi:10.3390/molecules171113530

Synthesis and Modifications of Phosphinic Dipeptide Analogues

Department of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland
Received: 17 October 2012 / Revised: 9 November 2012 / Accepted: 12 November 2012 / Published: 15 November 2012
(This article belongs to the Special Issue Organophosphorus Chemistry)
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Pseudopeptides containing the phosphinate moiety (-P(O)(OH)CH2-) 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.
Keywords: phosphinic peptides; P-C bond formation; multicomponent reactions; side-chain diversification; enzyme inhibition phosphinic peptides; P-C bond formation; multicomponent reactions; side-chain diversification; enzyme inhibition
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Mucha, A. Synthesis and Modifications of Phosphinic Dipeptide Analogues. Molecules 2012, 17, 13530-13568.

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