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Quantitation of Cysteine Residues Alkylated with 3-Bromopropylamine by Amino Acid Analysis

✍ Scribed by J.E. Hale; D.E. Beidler; R.A. Jue

Publisher: Elsevier Science
Year: 1994
Tongue: English
Weight: 410 KB
Volume: 216
Category: Article
ISSN: 0003-2697
DOI: 10.1006/abio.1994.1008

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✦ Synopsis

A new versatile reagent, 3-bromopropylamine, for the quantitative analysis of cysteine residues in proteins and peptides is reported. When added to amino acid standards, the 3-bromopropylamine derivative of cysteine, S-3-aminopropylcysteine, elutes in a unique position on four different amino acid analysis systems without modification to their standard gradients. Optimized conditions for the complete alkylation of cysteines in proteins with 3-bromopropylamine are described. The S-3-aminopropylcysteine is stable to standard acid hydrolysis conditions used for amino acid analysis. Cysteine values are within 10% of the predicted value in the amino acid analysis of acid hydrolysates of known proteins based on quantitation with S-3-aminopropylcysteine. No evidence of alkylation of other amino acids by 3-bromopropylamine is apparent from the amino acid analysis of proteins alkylated under the optimal conditions. These results expand the application of 3-bromopropylamine to include quantitation of cysteine by amino acid analysis as well as the previously reported identification of cysteines by protein sequencing.

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