Search results for "Tripeptides"

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Synthesis and activity of phosphinic tripeptide inhibitors of cathepsin C

2004

Phosphinic tripeptide analogues Gly-Xaaψ[P(O)(OH)CH2]-Gly have been developed as inhibitors of cathepsin C (DPP I), a lysosomal, papain-like cysteine protease. The target compounds were synthesised by addition of methyl acrylate to the appropriate phosphinic acids followed by the N-terminus elongation using mixed anhydride procedure. The latter step has been demonstrated to be a suitable method for N-terminal extension of the phosphinic pseudopeptide analogues without requirement of hydroxyphosphinyl protection. The title compounds appeared to be moderate inhibitors of the cathepsin C. However, although designed as transition state analogues, they surprisingly exhibited noncompetitive mode …

Cathepsinchemistry.chemical_classificationnoncompetitive inhibitionStereochemistryphosphinic tripeptidesOrganic ChemistryClinical BiochemistryPharmaceutical ScienceBiological activityPeptideTripeptidePhosphinic AcidsBiochemistryCysteine proteaseChemical synthesisCathepsin CCathepsin CNon-competitive inhibitionchemistryDrug DiscoveryMolecular MedicineProtease InhibitorsOligopeptidesMolecular BiologyBioorganic & Medicinal Chemistry Letters
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The infrared and Raman spectra of solid tridehydropeptides : influence of ΔAla and ΔPhe on the spectral profile

2012

Abstract A series of solid tripeptides Boc-Gly-X-Gly-OMe (X = dehydroalanine (ΔAla), dehydrophenylalanine (ΔPhe)) was investigated by Raman scattering and Fourier transform infrared spectra to examine the conformational marker bands of the unsaturated residue. The observed fundamental modes gave us the opportunity to analyze structural features that change due to the substitution of Ala by ΔAla and due to the different spatial arrangement of ΔPhe ( Z and E isomers). In addition, we showed the alteration of the spectral profile when the large size residue (Phe) is introduced into the backbone of the peptide with ΔPhe (in Boc-Gly-Δ (Z) Phe-Phe-OMe). The frequency ranges of interest included t…

ChemistryInfraredDehydrophenylalanineAnalytical chemistryTripeptidedehydrophenylalaninetripeptidesDehydroalanineFourier transform infrared spectrachemistry.chemical_compoundsymbols.namesakeCrystallographyDehydroalanineRaman bandAmideTripeptidessymbolsIRdhydroalanineRaman spectroscopyRamanSpectroscopyRaman scattering
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