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Formation of isoAsp
Stable Identifier
R-HSA-5685345
Type
Reaction [transition]
Species
Homo sapiens
Compartment
cytoplasm
ReviewStatus
5/5
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Metabolism of proteins (Homo sapiens)
Protein repair (Homo sapiens)
Formation of isoAsp (Homo sapiens)
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The layout of this reaction may differ from that in the pathway view due to the constraints in pathway layout
Beta-linked isoaspartyl (isoAsp) peptide bonds can arise spontaneously via succinimide-linked deamidation of asparagine (Asn) or dehydration of aspartate (Asp). The peptide bond becomes linked through the beta-carboxyl group of the Asp or Asn side-chain, leaving the alpha-carboxyl group of the original peptide bond free. The symmetry of the resulting succinimide intermediate leads to two possible products, either aspartate or isoaspartate, which is an atypical beta-amino acid. The mechanism favours approximately 7:3 the 'iso' form (Bornstein & Balian 1977, Aswad 1984, Murray & Clarke 1984, Di Donato et al. 1986). Formation of the succinimidyl intermediate and its cleavage occur spontaneously. The propensity to form isoaspartyl linkages depends on the residues flanking the asparaginyl site, with small resdiues such as Gly favouring linkage formation, as well as on the local conformation and flexibility of the polypeptide chain (Clarke 1987, Galletti et al. 1989).
These reactions are a significant source of protein damage under physiological conditions and represent both a mechanism that can usefully determine the lifetime of a protein (Robinson et al. 1970) and a component of the pathological process of ageing (Clarke 2003).
Literature References
PubMed ID
Title
Journal
Year
3440704
Propensity for spontaneous succinimide formation from aspartyl and asparaginyl residues in cellular proteins
Clarke, S
Int. J. Pept. Protein Res.
1987
Participants
Input
L-Arg,L-Asn [cytosol]
Output
L-Asp,isoAsp [cytosol]
Participates
as an event of
Protein repair (Homo sapiens)
Authored
Jupe, S (2015-01-05)
Reviewed
Meldal, BH (2015-10-05)
Created
Jupe, S (2015-03-27)
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