Quantitative mass spectral identification of p-bromophenylthiohydantoins from Edman degradations by tetradeuterated internal standards.

doi:10.1515/BCHM2.1976.357.2.1339

Paper

Quantitative mass spectral identification of p-bromophenylthiohydantoins from Edman degradations by tetradeuterated internal standards.

Published Dec 1, 1976 · M. Schneider, H. Tschesche

Hoppe-Seyler's Zeitschrift fur physiologische Chemie

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2

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Abstract

p-Bromophenylisothiocyanate is a reagent well suited for the Edman degradation of peptide chains[1-5]. The relative rate of the coupling reaction at the N-terminus is slightly more rapid than with phenyl- or methylisothiocyanate, but less rapid than with pentafluorophenylisothiocyanate. The latter reagent, however, is rapidly hydrolyzed under the conditions of the coupling reaction. The p-bromo substituent facilitates mass spectral identification of the p-bromophenylthiohydantoins obtained, due to its characteristic double peak[1-4]. Quantitation of the amount of p-bromophenylthiohydantoin obtained can easily be achieved in the parent mass spectrum by addition of a known amount of tetradeutero-p-bromophenylthiohydantoin as an internal standard. The tetradeuterated standards give rise to molecular ion peaks four mass units higher than the corresponding undeuterated probes. Standard and probe volatilize almost equally well. The composition in the vapor indicated by the H/D ratio reflects the molar concentrations over the entire range of probe evaporation. A procedure for the preparation of the tetradeutero-p-bromophenyl-isothiocyanate and the respective tetradeuterated amino acid p-bromophenylthiohydantoins is given.

Study Snapshot

p-bromophenylisothiocyanate is a suitable reagent for Edman degradation of peptide chains, and its double peak facilitates mass spectral identification of p-bromophenylthiohydantoins, enabling quantitative quantitation in parent

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Quantitative mass spectral identification of p-bromophenylthiohydantoins from Edman degradations by tetradeuterated internal standards.

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References

Citations

Chapter 32. The Use of Stable Isotopes in Medicinal Chemistry

Stable isotopes are useful in medicinal chemistry for structure elucidation, drug metabolism studies, pharmacokinetic analysis, and drug therapy, but their use faces challenges due to limited detection and synthesis costs.