The myrosinase-glucosinolate system to generate neoglycoproteins: A case study targeting mannose binding lectins

Cutolo, Giuliano; Didak, Blanka; Tomas, Josip; Roubinet, Benoît; Lafite, Pierre; Nehmé, Reine; Schuler, Marie; Landemarre, Ludovic; Tatibouët, Arnaud

doi:10.1016/j.carres.2022.108562

Cited by 3 publications

(1 citation statement)

References 26 publications

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“…In 2018, Tatibouёt and co-workers, reported the synthesis of mannoside-GSL conjugates, which allowed for myrosinase-triggered specific labelling of lectins [36] with released ITCs or synthesis of glycosylated proteins. [37] In 2019, we reported the synthesis and biochemical evaluation of GSL-N3 and GSL-BODIPY (Scheme 1B), first examples of an azide bearing and artificial, fluorescent GSL, respectively, forming fluorescent ITC-BODIPY in the presence of myrosinase. [38] Independently, Tatibouёt and co-workers, reported a similar approach for fluorescent GSLs and demonstrated their ability to serve as labelling probes for proteins.…”

Section: Introductionmentioning

confidence: 99%

Bioresponsive pseudoGlucosinolates (psGSLs) release Isothiocyanates (ITCs) in the Presence of Nitroreductases

Jimidar,

Ganskow,

Kagho

et al. 2024

Preprint

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Glucosinolates (GSLs) are secondary metabolites produced as part of an herbivore defence system in plants of the order Brassicales. GSLs release isothiocyanates (ITCs) upon activation by the myrosinase. Beyond their herbivore feeding deterrent properties, these ITCs have multiple interesting bioactivities. However, their release is limited by the presence of myrosinase. Here, we report the concept of pseudoglucosinolates (psGSLs) hijacking the natural release mechanism of GSLs for the release of ITCs and adapting it to nitroreductase as triggering enzymes. We provide the proof-of-concept for nitroreductase-responsive psGSLs and demonstrate their potential for peptide labelling and ITC-prodrug approaches.

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Section: Introductionmentioning

confidence: 99%

Bioresponsive pseudoGlucosinolates (psGSLs) release Isothiocyanates (ITCs) in the Presence of Nitroreductases

Jimidar,

Ganskow,

Kagho

et al. 2024

Preprint

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Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2021–2022

Harvey

2024

Mass Spectrometry Reviews

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The use of matrix‐assisted laser desorption/ionization (MALDI) mass spectrometry for the analysis of carbohydrates and glycoconjugates is a well‐established technique and this review is the 12th update of the original article published in 1999 and brings coverage of the literature to the end of 2022. As with previous review, this review also includes a few papers that describe methods appropriate to analysis by MALDI, such as sample preparation, even though the ionization method is not MALDI. The review follows the same format as previous reviews. It is divided into three sections: (1) general aspects such as theory of the MALDI process, matrices, derivatization, MALDI imaging, fragmentation, quantification and the use of computer software for structural identification. (2) Applications to various structural types such as oligo‐ and polysaccharides, glycoproteins, glycolipids, glycosides and biopharmaceuticals, and (3) other general areas such as medicine, industrial processes, natural products and glycan synthesis where MALDI is extensively used. Much of the material relating to applications is presented in tabular form. MALDI is still an ideal technique for carbohydrate analysis, particularly in its ability to produce single ions from each analyte and advancements in the technique and range of applications show little sign of diminishing.

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Enzyme-Triggered Chromogenic and Fluorogenic Probes for Myrosinase Activity Detection

Tomas,

Lafite,

Schuler

et al. 2024

J. Agric. Food Chem.

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Myrosinase, a thioglucosidase, is a key enzyme in the mechanism of defense of plants that hydrolyzes glucosinolates (GSLs) into isothiocyanates. These isothiocyanates are the main bioactive molecules exerting protective effect in Brassicales plants. These plants that contain this specific enzyme–substrate couple belong to our daily human diet and have demonstrated health benefits, such as chemopreventive effects. Thus, the detection of myrosinase activity is a key aspect of the production of isothiocyanates from glucosinolates. Two novel chromogenic and fluorogenic GSLs, GSL p-nitrophenoxy (GSL-pNP) and GSL-4-methylumbelliferone (GSL-4MU), were designed and synthesized to be used as simple and reliable molecular tools to spectrophotometrically detect myrosinase activity in simple and complex mixtures. Notably, the chromogenic GSL enabled the UV–vis detection and quantification of isolated myrosinase activity, while fluorogenic GSL could be used for in vitro activity monitoring of more complex plant materials, such as seeds.

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The myrosinase-glucosinolate system to generate neoglycoproteins: A case study targeting mannose binding lectins

Cited by 3 publications

References 26 publications

Bioresponsive pseudoGlucosinolates (psGSLs) release Isothiocyanates (ITCs) in the Presence of Nitroreductases

Bioresponsive pseudoGlucosinolates (psGSLs) release Isothiocyanates (ITCs) in the Presence of Nitroreductases

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2021–2022

Enzyme-Triggered Chromogenic and Fluorogenic Probes for Myrosinase Activity Detection

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