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. 1986 Jul;28(1):79-84.
doi: 10.1111/j.1399-3011.1986.tb03231.x.

Deamidation of the asparaginyl-glycyl sequence

Y C Meinwald, E R Stimson, H A Scheraga

Deamidation of the asparaginyl-glycyl sequence

Y C Meinwald et al. Int J Pept Protein Res. 1986 Jul.

Erratum in

  • Int J Pept Protein Res 1986 Dec;28(6):following 660

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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