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J. Biol. Chem., Vol. 264, Issue 11, 6164-6170, Apr, 1989
RC Stephenson and S Clarke
Nonenzymatic intramolecular reactions can result in the deamidation,
isomerization, and racemization of protein and peptide asparaginyl and
aspartyl residues via succinimide intermediates. To understand the sequence
dependence of these reactions, we measured the rate of succinimide
formation in a series of synthetic peptides at pH 7.4. These peptides
(Val-Tyr-Pro-X-Y-Ala) contained an internal aspartyl, asparaginyl, aspartyl
beta-methyl ester, or aspartyl alpha-methyl ester residue (X) followed by a
glycyl, seryl, or alanyl residue (Y). The rates of succinimide formation of
the asparaginyl peptides were found to be 13.1-35.6 times faster than those
of the aspartyl peptides. The rates of succinimide formation for the glycyl
peptides were 6.5-17.6 times faster than those of the alanyl peptides,
while the rates for the seryl peptides were 1.6-4.5 times faster than those
of the alanyl peptides. The overall 232-fold range in these reaction rates
for aspartyl and asparaginyl residues suggests that sequence can be an
important determinant in their stability in flexible peptides. In proteins,
there may be a much larger range in the rates of succinimide formation
because specific conformations may greatly enhance or inhibit this
reaction.
Succinimide formation from aspartyl and asparaginyl peptides as a model for the spontaneous degradation of proteins
Department of Chemistry and Biochemistry, University of California, Los Angeles 90024.
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