Synthesis and activity of phosphinic tripeptide inhibitors of cathepsin C

Mucha, Artur; Paweł, Małgorzata; Hurek, J.; Kafarski, Paweł

doi:10.1016/j.bmcl.2004.04.028

Cited by 20 publications

(8 citation statements)

References 38 publications

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“…31 The phosphinic pseudotetrapeptide Cbz-GlyGlyj[P(O)(OH)CH 2 ]-Gly-Gly-OH was synthesized by elongation of the N terminus of the appropriate tripeptide with N-benzyloxycarbonylglycine as described for shorter analogues. 27 The benzyloxycarbonyl group was removed from compound 3 (0.37 g, 1 mmol) by action of 33% HBr in AcOH (3 ml, 2 h). After evaporation to dryness the residue was additionally washed with diethyl ether (3!20 ml) to remove benzyl bromide.…”

Section: Hplc-based Activity Assaymentioning

confidence: 99%

Crystal Structures of Active LytM

Firczuk

Mucha²,

Bochtler³

2005

Journal of Molecular Biology

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132

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Section: Hplc-based Activity Assaymentioning

confidence: 99%

Crystal Structures of Active LytM

Firczuk

Mucha²,

Bochtler³

2005

Journal of Molecular Biology

Self Cite

100

132

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“…It comprised mainly di-or tripeptide derivatives functionalized with an electrophilic group, such as a vinyl sulfone, [22][23][24] 27 a semicarbazide moiety, 28 or a diazomethylketone. 29 A few peptides, [30][31][32] or the nonspecific cysteine protease inhibitor, E64, have also been found to inhibit cathepsin C. 32 To date, nonpeptidic inhibitors of cathepsin C have not been disclosed.…”

mentioning

confidence: 99%

Discovery of Novel Cyanamide-Based Inhibitors of Cathepsin C

Lainé

Palovich

McCleland

et al. 2010

ACS Med. Chem. Lett.

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“…The phosphinate functionality is poorly activated by standard coupling agents. The carboxylate can therefore be chemoselectively converted into the corresponding amide in the presence of the free phosphinic acid moiety, both in solution and on the solid phase by means of DCC (EDC)/HOBt, BOP, PyBOP, i -butyl chloroformate or other activators [ 32 , 36 , 61 , 84 , 85 ].…”

Section: Modifications Following the C-p-c Formationmentioning

confidence: 99%

Synthesis and Modifications of Phosphinic Dipeptide Analogues

Mucha

2012

Molecules

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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.

show abstract

Synthesis and activity of phosphinic tripeptide inhibitors of cathepsin C

Cited by 20 publications

References 38 publications

Crystal Structures of Active LytM

Crystal Structures of Active LytM

Discovery of Novel Cyanamide-Based Inhibitors of Cathepsin C

Synthesis and Modifications of Phosphinic Dipeptide Analogues

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