Denatured thiolated collagen. I. Synthesis and characterization

Biomaterials
F L Nicolas, Christian Henry Gagnieu

Abstract

A new thiolating reagent is used to introduce sulphur groups into denatured atelocollagen. The procedure is easy to control and applicable on a large scale. The reagent is a reactive dicarboxylic acid compound containing sulphur in the form of a disulphide functionality. It is prepared by reacting N,N'-disuccinoylcystamine with 1,1'-carbonyldiimidazole. When this reagent is added to a solution of denatured atelocollagen in dimethylsulphoxide, amide bonds are formed between the carbonyl functions of the reagent and epsilon-NH2 of lysine and hydroxylysine residues from the protein. The disulphide groups introduced can then be reduced by reaction with 1,4-dithiothreitol to give the-SH form of the modified protein. Control of the stoichiometry between the reagent and the protein can lead to varying modification levels. A maximum level of 0.33 mmol SH per gram of protein can be attained, which corresponds to complete thiolation of the lysine and hydroxylysine residues. Thiolated denatured atelocollagen exhibits gelatin-like behaviour, by being highly soluble in water at all pH values and by forming heat-reversible gels.

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Citations

Jul 18, 2015·International Journal of Molecular Sciences·Juan LiuArndt F Schilling
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May 4, 2011·Bioorganic & Medicinal Chemistry·Ziad OmranDonald Cairns

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