From Brassicacae Plants to Bioconjugation : A Journey with Glucosinolates

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From Brassicacae Plants to Bioconjugation : A Journey with Glucosinolates

Maria Domingues 1 , Laura Vidal Benet 1 , Giuliano Cutolo 1 , René De Vaumas 3 , Ludovic Landemarre 2 , Emilie Destandau 1 , Marie Schuler 1 , Arnaud Tatibouët 1

1 Université D'orléans - ICOA UMR 7311, Orléans, France, 2 GLYcoDiag, Orléans, France, 3Extrasynthese, Genay, France

Glucosinolates (GLs) are sulfur-containing secondary metabolites, specific biomarkers of the plants of the Brassicaceae family, involved in the mechanism of defense of these plants against aggressions. [1] The hydrolysis of the C-S anomeric bond by a specific β-thioglucohydrolase, myrosinase, lead to the formation of a transient thiohydroxamic species which in turn undergoes a Lossen rearrangement, thus liberating a sulfate ion and an isothiocyanate (ITC). Thanks to this unique biochemical transformation in Nature, glucosinolates are thus responsible for the multiple biological activities of these plants such as antifungal, antibacterial, antiviral or insecticidal properties. GLs and ITCs also have some beneficial impact on human health, with direct antitumor activity and chemopreventive effect. All known GLs (ca 140 molecules) all display a remarkable structural homogeneity based on a α-D-glucopyranosyl unit, a variable aglycon linked through an O-sulfated anomeric (Z)-thiohydroximate function. Thanks to their remarkable biological activities, glucosinolate extraction, analysis and synthesis have attracted numerous research efforts.

In this communication, we would like to focus on our recent results about (1) the extraction of glucosinolates and more specifically sulfur-containing rare glucosinolates from Camelina Sativa plant and (2) the development of efficient synthetic routes towards the gram-scale preparation of natural GLs.

Finally, we will also describe our recent results about the application of this enzymatic process to artificial synthetic glucosinolates in the light of its use as a potential new bioconjugational tool. [2] Indeed, as strong electrophiles, the ITCs are well known and useful in bioconjugation, but are toxic, not easy to prepare, to handle and to store. Using the natural MG reaction, we were able to prepare in-situ ITCs from the corresponding stable, non-toxic and water-soluble GL precursors. [3]

Summary of our activities around Glucosinolates (GLs)

a) Fahey, J. W.; Zalcmann, A. T.; Talalay, P. Phytochemistry 2001, 56, 5; b) Rollin, P.; Tatibouët, A. C. R. Chim. 2011, 14, 194.

Sletten, E.M.; Bertozzi, C. R. Angew. Chem. Int. Ed. 2009, 48, 6974.

a) Cutolo, G.; Reise, F.; Schuler, M.; Nehmé, R. ; Despras, G.; Brekalo, J.; Morin, Ph.; Renard, P.-Y.; Lindhorst, T. K.; Tatibouët, A. Org. Biomol. Chem. 2018, 16, 4900; b) Fredy, J. W.; Cutolo, G.; Poret, B.; Nehmé, R.; Hubert-Roux, M.; Gandolfo, P.; Castel, H.; Schuler, M.; Tatibouët, A.; Sabot, C.; Renard, P. -Y. Bioconjugate Chem. 2019, ASAP.

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