Click Chemistry-Assisted Bioconjugates for Hapten Immunodiagnostics
Bioorthogonal reactions have revolutionized the way low-molecular-weight compounds are coupled to biomolecules. Organic chemistry, polymer science, and chemical biology are among the disciplines that have benefited the most from this breakthrough. Despite the reliability of the click chemistry concept for the efficient and chemoselective functionalization of biomacromolecules with haptens at preferred positions, the fact that azide-alkyne cycloaddition reactions originate new chemical moieties as part of the linker may have delayed their application in the immunodiagnostic field. Using the mycotoxin ochratoxin A as a model compound, we herein demonstrate for the first time that bioconjugates arising from the ligation between an azido-bearing hapten and an alkyne-modified carrier protein are able to elicit the generation of high-affinity monoclonal antibodies suitable for the development of rapid methods for the immunodetection of small organic molecules.
López-Puertollano, Daniel,Agulló, Consuelo,Mercader, Josep V.,Abad-Somovilla, Antonio,Abad-Fuentes, Antonio
p. 956 - 964
(2020/04/09)
A new and expedient total synthesis of ochratoxin A and d 5-ochratoxin A
A new total synthesis of the mycotoxin ochratoxin A (OTA) is presented, in which it is prepared in 9% overall yield from commercially available substrates. The key step consists of the condensation reaction between protected L-phenylalanine and 5-chloro-8-hydroxy-3-methyl-1-oxoisochromane-7-carboxylic acid (ochratoxin α, OTα). The same strategy could be successfully applied to L-d5-phenylalanine, leading to the first total synthesis of d5-OTA, a molecular tracer for the detection and analytical quantification of the natural mycotoxin in food samples by means of stable isotope dilution assay (SIDA). Georg Thieme Verlag Stuttgart.
Gabriele, Bartolo,Attya, Mohamed,Fazio, Alessia,Di Donna, Leonardo,Plastina, Pierluigi,Sindona, Giovanni
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p. 1815 - 1820
(2010/02/28)
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