Abstract
Addition of cysteine to the double bonds of polydehydroalanine and copolymers of dehydroalanine (DHA) and methylcysteine, alanine, leucine or γ- methyl-L-glutamate is accompanied by increased solubility and decreased molecular weight. This result is due to a peptide bond cleavage caused by formation of a thiazolidine as a consequence of nucleophilic attack by the sulfur atom on the preceding C=0 group and subsequent splitting of the peptide bond by nucleophilic attack of an OH ion. This mechanism is predominant in alkaline media; in acid another mechanism is favoured; carbonyl-oxygen attacks the carbonyl-C-atom of the cysteine residue, forming a second ring system. Addition of one water molecule then yields two peptide fragments, one of them a terminal cysteine residue. Both mechanisms could be confirmed in the case of γ-L-glutamyl-dehydroalanyl-glycine by adding cysteine. Furthermore, it could be shown that SH-glutathione is decomposed at elevated temperatures according to the two mechanisms mentioned. This SH-induced pepetide bond cleavage can be used for selective peptide chain splitting of cysteine-containing polypeptides and proteins under relatively mild conditions.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsPreview
Unable to display preview. Download preview PDF.
References
Rossmeissl, G. (1973). Diplomarbeit, Marburg.
Ebert, Ch., Ebert, G. and Rossmeissl, G. (1976). Proc. Fifth Intern. Wool Textile Conf., Aachen, West Germany, I II, 97.
Rossmeissl, G. (1976). Thesis, Marburg.
Ebert, Ch. (1967). Diplomarbeit, Frankfurt.
Ebert, G., Ebert, Ch. and Wendorff, J. (1970). Kolloid Z. Z. Polym., 237, 229.
Ebert, Ch. (1971). Thesis, Marburg.
Utzinger, G. E., Strait, L. A. and Tuck, L. D. (1963). Experientia, 19, 324.
Utzinger, G. E. (1963). Experientia, 19, 327.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1977 Springer Science+Business Media New York
About this chapter
Cite this chapter
Ebert, C., Ebert, G., Rossmeissl, G. (1977). On the Specific Cleavage of Cysteine Containing Peptides and Proteins. In: Friedman, M. (eds) Protein Crosslinking. Advances in Experimental Medicine and Biology, vol 86. Springer, Boston, MA. https://doi.org/10.1007/978-1-4757-9113-6_14
Download citation
DOI: https://doi.org/10.1007/978-1-4757-9113-6_14
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4757-9115-0
Online ISBN: 978-1-4757-9113-6
eBook Packages: Springer Book Archive