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Arike"],"technology_type":["Data-dependent acquisition","Mass Spectrometry"],"software":[""],"submitter_keywords":["Pseudoglucosinolates","Isothiocanantes","Artificial gluscosinolates","Nitroreductase","Bioresponsive molecules"],"full_dataset_link":["https://www.ebi.ac.uk/pride/archive/projects/PXD065044"],"sample_protocol":["Samples (25 ul corresponding to approximately 10 ug) were purified using Pierce peptide desalting spin columns (Thermo Scientific), according to the manufacturer´s instructions. The samples were analyzed on an Orbitrap Lumos Tribrid mass spectrometer interfaced with an Easy-nLC1200 liquid chromatography system (both Thermo Fisher Scientific). Peptides (1 µg) were trapped on an Acclaim Pepmap 100 C18 trap column (100 μm x 2 cm, particle size 5 μm, Thermo Fisher Scientific) and separated on an in-house packed analytical column (45 cm x 75 μm, particle size 3 μm, Reprosil-Pur C18, Dr. Maisch) using a gradient from 4% to 28% acetonitrile in 0.1% formic acid over 32 min at a flow of 300 nL/min, followed by 13 minutes wash with 80% of acetonitrile in 0.1% formic acid. The precursor ion mass spectra were acquired at a resolution of 120 000 and an m/z range of 375-1500. Using a cycle time of 3 seconds and exclusion time of 30 seconds the most abundant precursors with charges 2–6 were isolated with an m/z window of 1.4 and fragmented by collision-induced dissociation (CID) at 30%. Fragment spectra were recorded in the Orbitrap at a resolution of 30000."],"repository":["Pride"],"quantification_method":["Not available"],"modification":[""],"data_protocol":["Raw files were processed and analyzed with Proteome Discoverer (Ver 3.0, Thermo Scientific). The data was matched against peptide sequences using Sequest as a search engine with a precursor tolerance of 5 ppm and a fragment ion tolerance of 0.03 Da. Addition of thiourea/dithiocarbamate (C,K), amidine (C/K) and deamidation (N) were set as variable modifications and cysteine carbamidomethylation was set as a fixed modification."],"omics_type":["Proteomics"],"labhead":["Philipp Klahn"],"instrument_platform":[""],"labhead_affiliation":["Department of Chemistry and Molecular Biology, University of Gothenburg, Natrium, Medicinaregatan 7B, 413 90, Gothenburg, Sweden"],"submission_type":["PARTIAL"],"species":["Synthetic Construct (code 12)"],"publication":["41998864 Jimidar CC, Ganskow CSG, Kagho MD, Chakrabarti A, Wiese L, Zollo M, Beutling U, Cesar LC, Morud J, Bugaj K, Brönstrup M, Sieber SA, Hacker SM, Klahn P. Bioresponsive pseudoGlucosinolates (psGSLs) Release Isothiocyanates (ITCs) in the Presence of Nitroreductases. Chemistry. 2026 32(25):e71012 10.1002/chem.71012"],"submitter_mail":["liisaarike@gmail.com"],"submitter_affiliation":["PhD"],"submitter_country":["Sweden"],"pubmed_abstract":["Glucosinolates (GSLs) are plant secondary metabolites that release bioactive isothiocyanates (ITCs) upon myrosinase-mediated activation. While ITCs display diverse antimicrobial and chemoprotective activities, their application is limited by dependence on myrosinase and intrinsic hydrolytic instability. Here, we introduce pseudoglucosinolates (psGSLs), a synthetic platform that mimics the natural GSL activation mechanism but replaces the thioglucosidic trigger with an enzyme-responsive para-aminobenzylthiol motif. Using nitroreductase (NfsB) as a noncanonical activating enzyme, we synthesized and characterized a series of nitro-masked psGSLs, including azide-, alkyne-, and fluorophore-functionalized derivatives. Enzymatic reduction induces a self-immolative 1,6-elimination and subsequent thio-Lossen rearrangement, releasing ITCs under physiological conditions. The liberated ITCs covalently modify peptides and proteins, showing predominant lysine reactivity in chemoproteomic analyses of the Staphylococcus aureus proteome, including functional sites of essential proteins. Fluorescent probes enabled visualization of enzyme-dependent protein labeling and demonstrated nitroreductase-triggered ITC release in vivo in Caenorhabditis elegans. Together, psGSLs establish a modular, bioresponsive prodrug and chemical biology platform for enzyme-controlled ITC delivery, expanding the scope of ITC-based covalent modification beyond natural myrosinase-dependent systems."],"pubmed_title":["Bioresponsive pseudoGlucosinolates (psGSLs) Release Isothiocyanates (ITCs) in the Presence of Nitroreductases."],"pubmed_authors":["Jimidar Claire C CC, Ganskow Charity S G CSG, Kagho Mervic D MD, Chakrabarti Aishi A, Wiese Lorenz L, Zollo Michael M, Beutling Ulrike U, Cesar Leona C LC, Morud Julia J, Bugaj Kamila K, Brönstrup Mark M, Sieber Stephan A SA, Hacker Stephan M SM, Klahn Philipp P"],"additional_accession":[]},"is_claimable":false,"name":"Bioresponsive pseudoGlucosinolates (psGSLs) release Isothiocyanates (ITCs) in the Presence of Nitroreductases","description":"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 the triggering enzymes. We provide proof-of-concept for nitroreductase-responsive psGSLs and demonstrate their potential for peptide labelling, ITC-prodrug approaches and for in vivo applications using the nematode of C. elegans","dates":{"publication":"2026-09-07","submission":"2025-06-16"},"accession":"PXD065044","cross_references":{"TAXONOMY":["NEWT:330879","NEWT:377960","NEWT:2042546","NEWT:259447","NEWT:295546","NCBITaxon:2719036","NEWT:625351","NCBITaxon:1280","NEWT:112503","NEWT:1129","NEWT:309807","NEWT:59753","NEWT:89184","NEWT:309800","NEWT:281395","NEWT:57577","NEWT:1211601","NEWT:876138","NEWT:44271","NEWT:193516","NEWT:1073882","NEWT:6819","NEWT:475174","NEWT:111205","NEWT:1117","NEWT:498257","NEWT:10036","NEWT:1590","NEWT:10034","NEWT:661410","NEWT:638632","NEWT:224326","NEWT:376619","NCBITaxon:79857","NEWT:1096976","NEWT:3765","NEWT:1589","NEWT:135622","NEWT:67352","NEWT:35786","NEWT:1580","NEWT:399784","NEWT:96731","NEWT:656064","NEWT:1582","NEWT:36630","NEWT:383379","NEWT:418106","NCBITaxon:12721","NEWT:10029","NEWT:913645","NEWT:641809","NEWT:1392488","NEWT:38815","NEWT:317447","NEWT:4688","NEWT:111225","NEWT:7719","NEWT:868565","NEWT:135674","NEWT:79329","NEWT:30069","NEWT:12637","NEWT:59729","NEWT:2164133","NEWT:295105","NEWT:29064","NEWT:108061","NEWT:60711","NEWT:224308","NEWT:273791","NEWT:3347","NEWT:160621","NEWT:212790","NEWT:110368","NEWT:1310161","NEWT:77133","NEWT:145481","NEWT:1310165","NEWT:29058","NCBITaxon:79824","NEWT:1912919","NEWT:410658","NEWT:44688","NEWT:44689","NEWT:498211","NEWT:347256","NEWT:5518","NEWT:398007","NEWT:1527468","NEWT:498217","NEWT:498216","NEWT:11320","NEWT:33554","NEWT:246196","NEWT:246197","NEWT:145458","NEWT:44685","NEWT:161934","NEWT:156587","NEWT:1148","NEWT:5508","NEWT:3329","NEWT:419481","NEWT:5507","NEWT:410661","NEWT:1140","NCBITaxon:2157","NEWT:1143","NEWT:1287689","NEWT:1094343","NEWT:1462472","NEWT:1336795","NEWT:644042","NEWT:150808","NEWT:1182590","NEWT:3712","NEWT:3711","NEWT:3714","NEWT:270643","NEWT:2065263","NEWT:177437","NEWT:10418","NEWT:118698","NEWT:1616117","NEWT:118696","NEWT:34865","NEWT:52283","NEWT:28174","NEWT:284812","NEWT:8175","NEWT:43330","NEWT:980415","NEWT:1603293","NEWT:44664","NEWT:43346","NEWT:3702","NEWT:66440","NEWT:1245466","NEWT:3704","NEWT:244366","NEWT:1246791","NEWT:176597","NEWT:118694","NEWT:2850","NEWT:118691","NEWT:34871","NEWT:33548","NEWT:52299","NEWT:8165","NEWT:96794","NEWT:34878","NEWT:3708","NEWT:332648","NEWT:44670","NEWT:536231","NEWT:376219","NEWT:219813","NEWT:1510","NEWT:460519","NEWT:1515","NEWT:572307","NEWT:1432138","NEWT:1424507","NEWT:1194599","NEWT:272844","NEWT:1348799","NEWT:33995","NEWT:55784","NEWT:1303443","NEWT:9483","NEWT:485","NEWT:56636","NEWT:2709072","NEWT:2499525","NEWT:2853422","NEWT:487","NEWT:1538553","NEWT:1679718","NEWT:480","NEWT:67767","NEWT:46835","NEWT:109757","NEWT:582580","NEWT:1185650","NEWT:216778","NEWT:294607","NEWT:1502","NEWT:128017","NEWT:376686","NEWT:237610","NEWT:95486","NEWT:119562","NEWT:1883446","NEWT:1233435","NEWT:118223","NEWT:11757","NEWT:109760","NEWT:29031","NEWT:317047","NEWT:491","NEWT:460523","NEWT:45954","NEWT:235443","NEWT:1757312","NEWT:85694","NEWT:109786","NEWT:108458","NEWT:5936","NEWT:320637","NEWT:1078283","NEWT:3750","NEWT:983964","NEWT:11706","NEWT:32644","NEWT:527796","NEWT:499175","NEWT:109779","NEWT:3745","NEWT:1715989","NCBITaxon:4751","NEWT:3747","NEWT:1116234","NEWT:1255228","NEWT:410289","NEWT:373153","NEWT:1640278","NEWT:472","NEWT:940825","NEWT:529507","NEWT:1071661","NEWT:28128","NEWT:470","NEWT:5911","NEWT:748693","NCBITaxon:50557","NEWT:39251","NEWT:29491","NEWT:101841","NEWT:446","NEWT:153481","NEWT:2014887","NEWT:33952","NEWT:445","NEWT:153009","NEWT:261756","NEWT:166313","NEWT:63366","NEWT:63367","NEWT:215402","NEWT:1547","NEWT:906914","NEWT:9031","NEWT:27292","NEWT:1050722","NEWT:3728","NEWT:108931","NEWT:1293497","NEWT:1055524","NEWT:150475","NEWT:267872","NEWT:381666","NEWT:172269","NEWT:9534","NEWT:5180","NEWT:256737","NEWT:9541","NEWT:8694","NEWT:33936","NEWT:8692","NEWT:2903","NEWT:185579","NEWT:13076","NEWT:207340","NEWT:172271","NEWT:1006581","NEWT:8673","NEWT:33940","NEWT:550","NEWT:554","NEWT:451516","NEWT:552","NEWT:1325291","NEWT:36185","NEWT:1054211","NEWT:1225786","NEWT:771870","NEWT:51338","NEWT:575412","NEWT:28112","NEWT:6493","NEWT:10832","NEWT:6494","NEWT:6491","NEWT:507601","NEWT:520","NEWT:186441","NEWT:643680","NEWT:214092","NCBITaxon:6157","NEWT:13095","NEWT:162425","NEWT:104105","NEWT:216257","NEWT:9986","NEWT:8654","NEWT:8658","NEWT:1268063","NEWT:8657","NEWT:9983","NEWT:8655","NEWT:5147","NEWT:28108","NEWT:28104","NEWT:407821","NEWT:568703","NCBITaxon:2","NEWT:568708","NEWT:1613","NEWT:986","NEWT:52641","NEWT:28532","NEWT:353152","NEWT:298176","NEWT:353153","NEWT:227377","NEWT:1774284","NEWT:40674","NEWT:1194669","NEWT:51329","NEWT:443906","NEWT:519","NEWT:2510939","NEWT:7394","NEWT:6063","NEWT:1328388","NEWT:105487","NEWT:1548728","NEWT:667127","NEWT:9557","NEWT:377586","NEWT:7375","NEWT:300641","NEWT:39655","NEWT:9554","NEWT:38323","NEWT:475932","NEWT:256318","NEWT:206411","NCBITaxon:6191","NEWT:229533","NEWT:2925","NEWT:214053","NEWT:28550","NEWT:80863","NEWT:90675","NEWT:52639","NEWT:52638","NEWT:57075","NE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