The destruction of serine and threonine thiohydantoins during the sequence determination of peptides by 4-N,N-dimethylaminoazobenzene 4′-isothiocyanate

作者: J.Y. Chang

DOI: 10.1016/0005-2795(79)90125-9

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摘要: Abstract 1. A mechanism for the destruction of serine and threonine thiohydantoins during protein sequence analysis by Edman-type degradation is proposed. The begins with dehydration side chains (at cyclization stage) which occurs mainly in anhydrous acid solution. dehydrated derivatives finally polymerize way reactive methylene group (enamine) to form polymers various molecular weights. In aqueous solution, undergo hydration (according Markovnikov rule) ring fission, leads irreversible breakdown thiohydantoin ring. derivative shows a much greater tendency these side-reactions than derivative. 2. presence oxygen, alkaline hydrolysis amino goes through an oxidation-deamination reaction at C-N bond formation thiourea keto acids. This accounts low recoveries obtained from thiohydantoins.

参考文章(12)
J Y Chang, E H Creaser, A novel manual method for protein-sequence analysis. Biochemical Journal. ,vol. 157, pp. 77- 85 ,(1976) , 10.1042/BJ1570077
J.Y. Chang, E.H. Creaser, Distinction of amino alcohols from amino acids by 4-N,N-dimethylaminoazobenzene-4'-isothiocyanate. Journal of Chromatography A. ,vol. 135, pp. 245- 248 ,(1977) , 10.1016/S0021-9673(00)86329-3
J.Y. Chang, E.H. Creaser, Improved chromatographic identification of coloured amino acid thiohydantoins Journal of Chromatography A. ,vol. 132, pp. 303- 307 ,(1977) , 10.1016/S0021-9673(00)89304-8
Pehr Edman, Eylif Dynesen, M. Webb, Max Rottenberg, Preparation of Phenyl Thiohydantoins from Some Natural Amino Acids. Acta Chemica Scandinavica. ,vol. 4, pp. 277- 282 ,(1950) , 10.3891/ACTA.CHEM.SCAND.04-0277
Bruce Africa, Frederick H. Carpenter, Alkaline hydrolysis of phenylthiohydantoins of amino acids Biochemical and Biophysical Research Communications. ,vol. 24, pp. 113- 119 ,(1966) , 10.1016/0006-291X(66)90418-9
D Ilse, P Edman, The Formation of 3-Phenyl-2-thiohydantoins from Phenylthiocarbamyl Amino Acids Australian Journal of Chemistry. ,vol. 16, pp. 411- 416 ,(1963) , 10.1071/CH9630411
Pehr Edman, K. J. Björkqvist, R. Reiter, E. Schønfeldt, Inger Steensgaard, Th. Rosenberg, Note on the Stepwise Degradation of Peptides via Phenyl Thiohydantoins. Acta Chemica Scandinavica. ,vol. 7, pp. 700- 701 ,(1953) , 10.3891/ACTA.CHEM.SCAND.07-0700
P. Edman, G. Begg, A Protein Sequenator FEBS Journal. ,vol. 1, pp. 80- 91 ,(1967) , 10.1111/J.1432-1033.1967.TB00047.X