Radiolytic degradation of the peptide main chain in dilute aqueous solution containing oxygen

Garrison, Warren M.; Kland-English, Mathilde; Sokol, Harvey A.; Jayko, Michael E.

doi:10.1021/j100720a007

Cited by 23 publications

(15 citation statements)

References 2 publications

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“…Now, previous work (16) has shown that glycylglycine undergoes the characteri sticpeptide reaction with the OH radical i. e. (17) which step in. oxygenated solution is followed by (18) As observed in the acetylglycine case, we find as shown in Table II In exp~aining the ;r-emarkably high yield of total ammonia, G(NH 3 ) = 4.58, from glycylglycirie, we note that in the earli(~r study of the radiolytic oxidation of alanine peptides (2) there was some eviden. :::e that the alkoxy radical sites formed in reaction of the type given in equations 11, 19 can react intramolecularly with other C-H linkages along the chain.…”

Section: Lbl-242supporting

confidence: 65%

Radiolytic Oxidation of Peptide Derivatives of Glycine in Aqueous Solution

Makada¹,

Garrison²

1972

Radiation Research

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Section: Lbl-242supporting

confidence: 65%

Radiolytic Oxidation of Peptide Derivatives of Glycine in Aqueous Solution

Makada¹,

Garrison²

1972

Radiation Research

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“…S1A and S1B). According to the proposed protein oxidative cleavage reaction (2,42), following the abstraction of an α-hydrogen at Gly31, a carbon-centered free radical derivative of bSOD1 is generated. carbon-centered radical thus formed is readily converted to alkoxyl radical leading to the cleavage of bSOD1 backbone at either side of Gly31 through the diamide or α-amidation pathways.…”

Section: Resultsmentioning

confidence: 99%

Distinct oxidative cleavage and modification of bovine [Cu– Zn]-SOD by an ascorbic acid/Cu(II) system: Identification of novel copper binding site on SOD molecule

Uehara

Luo

Aryal

et al. 2016

Free Radical Biology and Medicine

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We investigated the combined effect of ascorbate and copper [Asc/Cu(II)] on the integrity of bovine [Cu-Zn]-superoxide dismutase (bSOD1) as a model system to study the metal catalyzed oxidation (MCO) and fragmentation of proteins. We found Asc/Cu(II) mediates specific cleavage of bSOD1 and generates 12.5 and 3.2 kDa fragments in addition to oxidation/carbonylation of the protein. The effect of other tested transition metals, a metal chelator, and hydrogen peroxide on the cleavage and oxidation indicated that binding of copper to a previously unknown site on SOD1 is responsible for the Asc/Cu(II) specific cleavage and oxidation. We utilized tandem mass spectrometry to identify the specific cleavage sites of Asc/Cu(II)-treated bSOD1. Analyses of tryptic- and AspN-peptides have demonstrated the cleavage to occur at Gly31 with peptide bond breakage with Thr30 and Ser32 through diamide and α-amidation pathways, respectively. The three-dimensional structure of bSOD1 reveals the imidazole ring of His19 localized within 5 Angstrom from the α-carbon of Gly31 providing a structural basis that copper ion, most likely coordinated by His19, catalyzes the specific cleavage reaction.

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“…1, 14-18, then it is clear that ammonia and carbonyl yields with y-rays should be in the relationship G(NH 3 ) ~ G(R 2 CO) ~ G(OH) ~ 3. Quantitative assays of the ammonia and carbonyl yields from a series of model peptide derivatives including·acetyl-glycine, acetylalanine, glycine anhydride, etc., consistently show G(NH 3 ) ~ 3 for eac~ system (Atkins et al~ 1967;Garrison et al:, 1970). However, it was also found that the yield of carbonyl products from these simple peptide systems is not in accord with the quantitative requirements of the reaction sequence 14-18.…”

mentioning

confidence: 80%

“…Specific chemical evidence for oxidative degradation of the peptide main chain through OH attack at a C-H bonds along the chain to yield amide and keto acid functions was first represented in terms of the overall stoichiometry (Jayko et al, 1958;Garrison et al, 1962;Garrison et al, 1970).…”

mentioning

confidence: 99%