Reductive Modification of a Methionine Residue in the Amyloid‐β Peptide

Kadlcik, V.; Sicard-Roselli, Cécile; Houée-Levin⊥, Chantal; Kodı́ček, Milan; Ferreri, Carla; Chatgilialoglu, Chryssostomos

doi:10.1002/anie.200503942

Cited by 35 publications

(37 citation statements)

References 27 publications

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“…The sequence of amyloid -peptide of 40 amino acids, where only the Met residue is present as a S-containing amino acid, was also studied for its connections with the alteration reported in the Alzheimer disease. In this case, reductive stress was able to produce the selective desulfurization of this sequence, and the identification of the resulting Aba-modified peptide has been possible (Kadlcik et al, 2006).…”

Section: Radical-based Modifications For Protein Librariesmentioning

confidence: 97%

Biomimetic Chemistry: Radical Reactions in Vesicle Suspensions

Chatgilialoglu¹,

Ferreri²

2010

Biomimetics Learning From Nature

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Section: Radical-based Modifications For Protein Librariesmentioning

confidence: 97%

Biomimetic Chemistry: Radical Reactions in Vesicle Suspensions

Chatgilialoglu¹,

Ferreri²

2010

Biomimetics Learning From Nature

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“…6). The model has been applied to a variety of Scontaining proteins and petides, such as bovine pancreatic RNase, lysozime, amyloid(b-peptide, and met-enkephalin [30][31][32][33]. Such examples served to establish the molecular basis for a tandem protein-lipid damage.…”

Section: In Vivo Lipid Isomerization: the Real Culpritsmentioning

confidence: 99%

Trans Fatty Acids in Membranes: The Free Radical Path

2007

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The double bond geometry of most of the naturally occurring unsaturated fatty acid residues is cis. Due to the relevance of fatty acids as structural components of cell membranes and as biologically active molecules, the change of the cis geometry means a change of the associated functions and activities. The finding that the cis to trans isomerization is effective in phospholipids by the intervention of radical species led to the discovery that there can indeed occur an endogenous formation of trans fatty acids, whose significance in biological systems started to be addressed with in vitro and in vivo studies. Studies of liposome models simulating the formation of isomerizing species and evaluating their ability to interact with the hydrophobic part of the membrane bilayer has contributed to the gain in knowledge of the fundamental features of the lipid isomerization in membranes. Further work is in progress for the identification of the real culprits of the in vivo lipid isomerization, and recent results are shown on oleic acid micelles, where *NO2 radicals are not able to induce double bond isomerization in comparison with amphiphilic thiol, such as 2-mercaptoethanol. H2S and sulfur-containing amino acid residues are two of the possible species involved in this process at a biological level. An update of the scenario of the geometrical isomerization in membranes by free radicals is provided, together with applications and perspectives in life sciences.

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“…In some conformations it reached lower (1.3 V) or much higher values (2 V). Experimental results indicated such possible variations [28][29][30]. One might try to predict the values by looking at the atoms in the neighbourhood of the sulphur atom.…”

Section: Calculations Of Redox Couple Potentialsmentioning

confidence: 99%

“…H atoms are also created in much lower yield (0.05 μmol J −1 ), which lead to de-sulphuration of methionine [11]. The H 2 O 2 yield is also lower (0.07 μmol J −1…”

Section: Introductionmentioning

confidence: 99%

Methionine one-electron oxidation: Coherent contributions from radiolysis, IRMPD spectroscopy, DFT calculations and electrochemistry

Scuderi

Bergès

Oliveira

et al. 2016

Radiation Physics and Chemistry

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Methionine is an essential amino acid, unfortunately prone to oxidation. The mechanism of its oxidation by • OH radicals has been studied for more than 40 years and still remains misunderstood. We have reinvestigated the oxidation of this residue in model peptides, aiming at i) improving the identification of free radicals by the use of more modern quantum chemistry methods; ii) reinvestigating the one-electron reduction potentials as a function of the position in the sequence; iii) identifying the final compounds, which were still unknown; iv) reinvestigating the intramolecular electron transfer (IET) involving this residue.

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Reductive Modification of a Methionine Residue in the Amyloid‐β Peptide

Cited by 35 publications

References 27 publications

Biomimetic Chemistry: Radical Reactions in Vesicle Suspensions

Biomimetic Chemistry: Radical Reactions in Vesicle Suspensions

Trans Fatty Acids in Membranes: The Free Radical Path

Methionine one-electron oxidation: Coherent contributions from radiolysis, IRMPD spectroscopy, DFT calculations and electrochemistry

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