Synthesis Of Haptens For Tris (2,3-dibromopropyl) Isocyanurate Containing Amino Function Group

Persistent Organic Pollutants (POPs) is a kind of toxic organic compounds which can exist in the environment for a long time and transport a long distance in the environment. The existence of these compounds poses adverse effect to human beings and ecosystem. Recent advances in the research of artificial antigen have shown that artificial antigens can be a valuable approach for the treatment of some diseases as well as the detection of pesticide residues. By coupling haptens to an appropriated carrier, artificial antigen can induce animals to produce hapten-specific antibody. Based on this principle a new analytical method, immunological analysis has been recently developed. Compared to the conventional analytical technologies, such as chromatographic methods, this method offers an alternative with high specificity, sensitivity for the analysis of a large number of samples in a short time.Tris (2,3-dibromopropyl) isocyanurate(TBC) is a heterocyclic hexabrominated additive flame retardant that possess the typical characteristics of persistent organic pollutants (POPs), which is resistant to photodegradation, durable, and thermally stable and has adverse effect to the ecosystems and human health.TBC is a small organic compound which is non-immunogenic. Hence, it is necessary to design appropriate chemical structures that can be covalently coupled to a carrier protein. In order to find the hapten structures and activity relationship of the final antibody, we are committed to the following two researches:Firstly, intermediate compound 3 was synthesized via Intra-rearrangement reaction and the yiled was optimized to 69%, then the first series of haptens with aromatic function group for TBC have been successfully obtained via Williamenson ether reaction, Nucleophilic substitution reaction, Bromination, Gabriel reaction, Reductive reaction. The reason for introducing amine to the structure is that it could react with carboxylic group of the protein carrier to form peptide bond. We designed four haptens for TBC with different length of alkyl chains in order to find how the length of spacer arms influence the conjugation of generating antigens and the final production of antibody.Secondly, the other series haptens with aliphatic function group for TBC have been successfully obtained via Gabriel reaction. These series haptens are all without aromatic rings. As we all know, when the aromatic ring was introduced to the target compounds, it will change the original structures which may affect the specificity of the final antibody. In this case, we designed and synthesized this series compounds without aromatic ring to find to what extent the benzene ring affect the final specificity.