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

Synthesis and Modifications of Phosphinic Dipeptide Analogues

Received: 17 October 2012; in revised form: 9 November 2012 / Accepted: 12 November 2012 / Published: 15 November 2012
(This article belongs to the Special Issue Organophosphorus Chemistry)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: 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
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MDPI and ACS Style

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

AMA Style

Mucha A. Synthesis and Modifications of Phosphinic Dipeptide Analogues. Molecules. 2012; 17(11):13530-13568.

Chicago/Turabian Style

Mucha, Artur. 2012. "Synthesis and Modifications of Phosphinic Dipeptide Analogues." Molecules 17, no. 11: 13530-13568.

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