Literature DB >> 2520758

Deamidation via cyclic imide in asparaginyl peptides.

S Capasso1, L Mazzarella, F Sica, A Zagari.   

Abstract

The deamidation reaction of asparaginyl peptides was studied as a function of the pH and sequence. The deamidation of Boc-Asn-Gly-Gly-NH2 and the hydrolysis of the corresponding aminosuccinyl (Asu) peptide, Boc-Asu-Gly-Gly-NH2, were carried out in the pH ranges 5-10, whereas the deamidation of Boc-Asn-Ala-Gly-NH2, Boc-Asn-Gly-Ala-NH2 and Boc-Asn-Ser-Gly-NH2 was studied at pH 8.9 only. In each case, the conversion of the amide side-chain moiety of the Asn to carboxyl group occurs via a succinimide intermediate (Asu), and its breakdown leads to a normal and an isoaspartyl peptide. The kinetic constants of the Asu formation and the hydrolytic step increase markedly at basic pH. The influence of the side chain of the residue next to Asn is also discussed.

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Year:  1989        PMID： 2520758

Source DB:  PubMed          Journal:  Pept Res        ISSN： 1040-5704


  15 in total

1.  The effects of alpha-helix on the stability of Asn residues: deamidation rates in peptides of varying helicity.

Authors:  A A Kosky; U O Razzaq; M J Treuheit; D N Brems
Journal:  Protein Sci       Date:  1999-11       Impact factor: 6.725

2.  Chemical pathways of peptide degradation. III. Effect of primary sequence on the pathways of deamidation of asparaginyl residues in hexapeptides.

Authors:  K Patel; R T Borchardt
Journal:  Pharm Res       Date:  1990-08       Impact factor: 4.200

3.  Identification of sites of degradation in a therapeutic monoclonal antibody by peptide mapping.

Authors:  D J Kroon; A Baldwin-Ferro; P Lalan
Journal:  Pharm Res       Date:  1992-11       Impact factor: 4.200

4.  Kinetics and mechanisms of deamidation and covalent amide-linked adduct formation in amorphous lyophiles of a model asparagine-containing Peptide.

Authors:  Michael P Dehart; Bradley D Anderson
Journal:  Pharm Res       Date:  2011-10-18       Impact factor: 4.200

5.  Thermodynamic analysis of the effect of selective monodeamidation at asparagine 67 in ribonuclease A.

Authors:  F Catanzano; G Graziano; S Capasso; G Barone
Journal:  Protein Sci       Date:  1997-08       Impact factor: 6.725

6.  Engineering deamidation-susceptible asparagines leads to improved stability to thermal cycling in a lipase.

Authors:  K Bhanuramanand; Shoeb Ahmad; N M Rao
Journal:  Protein Sci       Date:  2014-08-05       Impact factor: 6.725

7.  Chemical pathways of peptide degradation. II. Kinetics of deamidation of an asparaginyl residue in a model hexapeptide.

Authors:  K Patel; R T Borchardt
Journal:  Pharm Res       Date:  1990-07       Impact factor: 4.200

Review 8.  Protein damage and methylation-mediated repair in the erythrocyte.

Authors:  P Galletti; D Ingrosso; C Manna; G Clemente; V Zappia
Journal:  Biochem J       Date:  1995-03-01       Impact factor: 3.857

9.  Distinguishing Aspartic and Isoaspartic Acids in Peptides by Several Mass Spectrometric Fragmentation Methods.

Authors:  Nick DeGraan-Weber; Jun Zhang; James P Reilly
Journal:  J Am Soc Mass Spectrom       Date:  2016-09-09       Impact factor: 3.109

10.  Chemical pathways of peptide degradation. VI. Effect of the primary sequence on the pathways of degradation of aspartyl residues in model hexapeptides.

Authors:  C Oliyai; R T Borchardt
Journal:  Pharm Res       Date:  1994-05       Impact factor: 4.200
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