Synthesis of stable isotope‐labeled nasturlexins and potential precursors to probe biosynthetic pathways of cruciferous phytoalexins

Pedras, M. Soledade C.; To, Quang Huy

doi:10.1002/jlcr.3591

Cited by 9 publications

(8 citation statements)

References 22 publications

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“…Nasturlexins are an unusual class of natural products found in plants because of their rare dithiocarbamate functionality. Deuterated representatives of this family were synthesized from deuterated benzaldehyde . Original deuterated compounds are commercially available, such as (bromomethyl)cyclopropane- d 3 , 2-cyanopyridine- d 4 .…”

Section: Miscellaneous Transformations With Deuterium Incorporationmentioning

confidence: 99%

“…Deuterated representatives of this family were synthesized from deuterated benzaldehyde. 384 Original deuterated compounds are commercially available, such as (bromomethyl)cyclopropane-d 3 , 2-cyanopyridine-d 4 . The former leads to labeled CHF6001 and a potent phosphodiesterase 4 inhibitor in 10 steps with an overall yield of 9%; the latter initiates the synthesis of a potent lymphocyte functionassociated antigen-1 inhibitor.…”

Section: Multistep Syntheses With Deuterium Incorporationmentioning

confidence: 99%

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Recent Developments for the Deuterium and Tritium Labeling of Organic Molecules

et al. 2022

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Organic compounds labeled with hydrogen isotopes play a crucial role in numerous areas, from materials science to medicinal chemistry. Indeed, while the replacement of hydrogen by deuterium gives rise to improved absorption, distribution, metabolism, and excretion (ADME) properties in drugs and enables the preparation of internal standards for analytical mass spectrometry, the use of tritium-labeled compounds is a key technique all along drug discovery and development in the pharmaceutical industry. For these reasons, the interest in new methodologies for the isotopic enrichment of organic molecules and the extent of their applications are equally rising. In this regard, this Review intends to comprehensively discuss the new developments in this area over the last years (2017−2021). Notably, besides the fundamental hydrogen isotope exchange (HIE) reactions and the use of isotopically labeled analogues of common organic reagents, a plethora of reductive and dehalogenative deuteration techniques and other transformations with isotope incorporation are emerging and are now part of the labeling toolkit.

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Section: Miscellaneous Transformations With Deuterium Incorporationmentioning

confidence: 99%

Section: Multistep Syntheses With Deuterium Incorporationmentioning

confidence: 99%

Recent Developments for the Deuterium and Tritium Labeling of Organic Molecules

et al. 2022

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“…Owing to their interesting biological activities, natural GSLs have been the target of several total syntheses . Additionally, the syntheses of several artificial GSLs bearing unnatural or isotopically labeled aglycones and glucose units as well as α‐anomeric GSLs have been reported. Very recently, Tatibouët and co‐workers reported a mannoside–GSL glycoconjugate as labeling probe for lectins .…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Biochemical Evaluation of an Artificial, Fluorescent Glucosinolate (GSL)

et al. 2019

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The synthesis of the first example of a fluorescent glucosinolate (GSL)–BODIPY conjugate based on an azide‐containing artificial GSL precursor (GSL‐N3) is reported. Biochemical evaluation of the artificial GSLs revealed that the compounds are converted to the corresponding isothiocyanates in the presence of myrosinase. Furthermore, myrosinase‐catalyzed hydrolysis in the presence of plant specifier proteins yielded the expected alternative products, namely nitriles. The easy assembly of the fluorescent GSL–BODIPY conjugate by click chemistry from GSL‐N3 holds potential for application as a fluorescence labeling tool to investigate GSL‐associated processes.

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“…Isotopically labeled compounds have been numbered identically to non-labeled compounds followed by a letter,with different letters indicating different isotopic composition, e.g., 10a and 10b. The isotopically labelled benzylisothiocyanate (9a) and methyl benzyldithiocarbamate 15a were synthesized (Pedras and To, 2018a) as summarized in Fig. 6 and reported in Supplementary Information.…”

Section: Biosynthetic Origin: Feeding Experiments With Isotopically Labeled Compounds and Analyses Of Isotope Incorporationsmentioning

confidence: 99%

Expanding the Phytoalexin Chemical Space: Tropalexins a and B from Tropaeolum Majus Suggest Evolutionary Conservation of Biosynthetic Enzymes

Pedras¹,

Alavi²

2020

Preprint

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Tropalexins A and B, the first phytoalexins isolated from Tropaeolum majus (Brassicales order, Tropaeolaceae family), together with their antifungal activity and biosynthetic precursors are disclosed. These plant defenses contain a 1,3-benzothiazine ring and are shown to derive from Phe via the glucosinolate glucotropaeolin, which indicates that T. majus employs a phytoalexin biosynthetic pathway closely related to the pathway operating in Brassica spp. (Brassicales order, Brassicaceae family) and suggests an evolutionary conservation of key biosynthetic enzymes

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Synthesis of stable isotope‐labeled nasturlexins and potential precursors to probe biosynthetic pathways of cruciferous phytoalexins

Cited by 9 publications

References 22 publications

Recent Developments for the Deuterium and Tritium Labeling of Organic Molecules

Recent Developments for the Deuterium and Tritium Labeling of Organic Molecules

Synthesis and Biochemical Evaluation of an Artificial, Fluorescent Glucosinolate (GSL)

Expanding the Phytoalexin Chemical Space: Tropalexins a and B from Tropaeolum Majus Suggest Evolutionary Conservation of Biosynthetic Enzymes

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