Literature DB >> 3759344

Deamidation of the asparaginyl-glycyl sequence.

Y C Meinwald, E R Stimson, H A Scheraga.   

Abstract

The deamidation of Ac-Asn-Gly-NHMe and Ac-Isn-Gly-NHMe has been studied as a model for the facile deamidation of the Asn-Gly sequence in proteins. At alkaline pH, the product in each case is an identical mixture of Ac-alpha-Asp-Gly-NHMe (approximately 22%) and Ac-beta-Asp-Gly-NHMe (approximately 78%) as determined by n.m.r. spectroscopy. Because this same ratio is obtained from both Ac-Asn-Gly-NHMe and Ac-Isn-Gly-NHMe, the postulated mechanism, that deamidation proceeds through a cyclic imide intermediate, is confirmed. Unlike peptides of aspartyl esters, cyclization does not occur under nonaqueous conditions or at low pH in aqueous solution.

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Year:  1986        PMID： 3759344     DOI： 10.1111/j.1399-3011.1986.tb03231.x

Source DB:  PubMed          Journal:  Int J Pept Protein Res        ISSN： 0367-8377


  24 in total

1.  Protein deamidation.

Authors:  Noah E Robinson
Journal:  Proc Natl Acad Sci U S A       Date:  2002-04-16       Impact factor: 11.205

2.  Deamidation of human proteins.

Authors:  N E Robinson; A B Robinson
Journal:  Proc Natl Acad Sci U S A       Date:  2001-10-16       Impact factor: 11.205

3.  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

4.  Identification and characterization of an anti-isoaspartic acid monoclonal antibody.

Authors:  S R Lehrman; D M Hamlin; M E Lund; G A Walker
Journal:  J Protein Chem       Date:  1992-12

Review 5.  Stability of protein pharmaceuticals.

Authors:  M C Manning; K Patel; R T Borchardt
Journal:  Pharm Res       Date:  1989-11       Impact factor: 4.200

6.  Quantitating the relative abundance of isoaspartyl residues in deamidated proteins by electron capture dissociation.

Authors:  Jason J Cournoyer; Cheng Lin; Michael J Bowman; Peter B O'Connor
Journal:  J Am Soc Mass Spectrom       Date:  2006-09-25       Impact factor: 3.109

7.  Stepwise deamidation of ribonuclease A at five sites determined by top down mass spectrometry.

Authors:  Vlad Zabrouskov; Xuemei Han; Ervin Welker; Huili Zhai; Cheng Lin; Klaas J van Wijk; Harold A Scheraga; Fred W McLafferty
Journal:  Biochemistry       Date:  2006-01-24       Impact factor: 3.162

8.  Mechanisms of glucagon degradation at alkaline pH.

Authors:  Nicholas Caputo; Jessica R Castle; Colin P Bergstrom; Julie M Carroll; Parkash A Bakhtiani; Melanie A Jackson; Charles T Roberts; Larry L David; W Kenneth Ward
Journal:  Peptides       Date:  2013-05-04       Impact factor: 3.750

9.  Solution structure of murine epidermal growth factor: determination of the polypeptide backbone chain-fold by nuclear magnetic resonance and distance geometry.

Authors:  G T Montelione; K Wüthrich; E C Nice; A W Burgess; H A Scheraga
Journal:  Proc Natl Acad Sci U S A       Date:  1987-08       Impact factor: 11.205

10.  Formation of isoaspartate 99 in bovine and porcine somatotropins.

Authors:  B N Violand; M R Schlittler; P C Toren; N R Siegel
Journal:  J Protein Chem       Date:  1990-02
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