16281-39-3Relevant articles and documents
Click Chemistry-Assisted Bioconjugates for Hapten Immunodiagnostics
López-Puertollano, Daniel,Agulló, Consuelo,Mercader, Josep V.,Abad-Somovilla, Antonio,Abad-Fuentes, Antonio
, p. 956 - 964 (2020)
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.
First synthesis of a stable isotope of Ochratoxin A metabolite for a reliable detoxification monitoring
Bouisseau, Anais,Roland, Aurelie,Reillon, Florence,Schneider, Remi,Cavelier, Florine
supporting information, p. 3888 - 3890 (2013/09/02)
Due to its toxicity and presence in numerous food products, Ochratoxin A (OTA) has drawn attention for decades. This article summarizes the first synthesis of a labeled analogue of Ochratoxin α (OTα), one of the main products generated by the metabolization of OTA by microorganisms. This synthesis also led to a new labeled analogue of OTA with the deuteration located on the dihydroisocoumarin moiety allowing thus both the accurate quantification of OTA and OTα and the establishing of a reliable detoxification rate.
A new and expedient total synthesis of ochratoxin A and d 5-ochratoxin A
Gabriele, Bartolo,Attya, Mohamed,Fazio, Alessia,Di Donna, Leonardo,Plastina, Pierluigi,Sindona, Giovanni
body text, p. 1815 - 1820 (2010/02/28)
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.
