Design and synthesis of geosmin derivatives using organic synthesis strategies and application in antibody production

ABSTRACT To develop a sensitive and specific ELISA for geosmin (GSM), the research of this study is focused on the design and synthesis of several GSM derivatives, which maintain the whole GSM structure as much as possible and contain a spacer arm with an active group at the end. To form the GSM backbone, tandem organic reaction strategies were used to replace the traditional Robinson cyclization reaction. Five GSM derivatives were synthesized and the formed GSM derivative-protein conjugates were used as the immunogens for the production of polyclonal antibodies against GSM, while four GSM derivatives were synthesized and the GSM derivative-protein conjugates were used as coating antigens for establishing ELISA. The relationship between the structures of GSM derivatives and the antibody properties was explored. Under optimal conditions, the LOD of the ELISA for GSM was found to be 0.16 ng mL−1, and the antiserum was able to specifically recognize the GSM backbone.