Journal of Organic Chemistry p. 2014 - 2021 (1983)
Update date:2022-08-05
Topics:
Capecchi, John T.
Miller, Marvin, J.
Loudon, G. Marc
Coupling of O-pivaloylhydroxylamine (4) and subsequent Lossen rearrangement under mild conditions led to the disappearence of β-aspartyl and γ-glutamyl residues from subsequent amino acid analysis in a variety of peptides.Residues from the usual α linkage rearrange much more sluggishly to products that are detectable by amino acid analysis.An interesting complication in the procedure is that α-linked glutamyl residues are converted in part to a 2-oxohexahydropyrimidine-4-carboxylic acid derivative which is stable to extended acid hydrolysis.After base hydrolysis this deri vative yields 2,4-diaminobutanoic acid.This reaction explains aberrant results in the linkage analysis of collagen that have been reported in the literature.
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