{"id":"W4391659489","doi":"10.1021/jacs.3c14434","title":"Boronic Acid-Catalyzed Regio- and Stereoselective <i>N</i>-Glycosylations of Purines and Other Azole Heterocycles: Access to Nucleoside Analogues","year":2024,"lang":"en","type":"article","venue":"Journal of the American Chemical Society","topic":"Carbohydrate Chemistry and Synthesis","field":"Chemistry","cited_by":29,"is_retracted":false,"has_abstract":true,"ca_institutions":"University of Toronto","funders":"Natural Sciences and Engineering Research Council of Canada; Alliance de recherche numérique du Canada; Kennarshore; Canada Foundation for Innovation","keywords":"Chemistry; Azole; Glycosylation; Stereoselectivity; Glycosyl; Nucleoside; Catalysis; Combinatorial chemistry; Glycosyl donor; Furanose; Purine metabolism; Stereochemistry; Boronic acid; Organic chemistry; Enzyme; Ring (chemistry); Biochemistry; Antifungal","routes":{"ca_aff":true,"ca_fund":true,"ca_venue":false,"about_ca":false,"invisible_to_affiliation_only":false},"retraction":null,"screen":null,"direct_labels":[],"prediction":{"model_version":"metacan-v3-hybrid-931329e0061c","candidate_categories":[],"consensus_categories":[],"category_scores_codex":[0.000122467,0.0003546047,0.0002726343,0.0001026127,0.0001358638,0.0002414201,0.0002978292,0.0002098867,0.0008406417],"category_scores_gemma":[0.0001209223,0.0001232633,0.0002117779,0.0001244078,0.0001341042,0.0002650849,0.000172275,0.000236089,0.0003037468],"about_ca_system_candidate":false,"about_ca_system_consensus":false,"about_ca_system_score_codex":0.0004069467,"about_ca_system_score_gemma":0.0002429983,"about_ca_topic_candidate":false,"about_ca_topic_consensus":false,"about_ca_topic_score_codex":0.00143305,"about_ca_topic_score_gemma":0.002528326,"domain_scores_codex":[0.9999533,0.000006841688,0.000002246132,0.000008927625,0.00001054707,0.00001825181],"domain_scores_gemma":[0.9999784,0.000004547055,0.000007650705,0.000001701781,0.000002870049,0.000004894625],"domain_codex":null,"domain_gemma":null,"domain_candidate":null,"domain_consensus":null,"study_design_codex":"bench_or_experimental","study_design_gemma":"bench_or_experimental","study_design_scores_codex":[0.0005568351,0.0002069141,0.0009096878,0.0005061795,0.00006226663,0.0003384624,0.00009881921,0.01719705,0.9507214,0.006378545,0.0006019439,0.02242186],"study_design_scores_gemma":[0.0001188853,0.0006119164,0.0009572388,0.0000220969,0.00003958023,0.0002746595,0.00004917475,0.04116576,0.9504018,0.001044638,0.005275157,0.00003915348],"study_design_candidate":"bench_or_experimental","study_design_consensus":"bench_or_experimental","genre_codex":"empirical","genre_gemma":"empirical","genre_scores_codex":[0.9778178,0.001565698,0.01106974,0.00007973791,0.0000340292,0.00004521169,0.0002222115,0.0001185963,0.009046975],"genre_scores_gemma":[0.9941163,0.001100717,0.003424612,0.00001558934,0.00000281596,0.00001723253,0.0001443176,0.00001535104,0.001162936],"genre_candidate":"empirical","genre_consensus":"empirical","teacher_disagreement_score":0.00143305,"threshold_uncertainty_score":0.002952635,"prediction_status":"machine_predicted_unvalidated"},"machine_scores":{"provisional":true,"baseline":true,"maturity_gate_passed":false,"score_opus":0.01619244857321383,"score_gpt":0.2717633610678393,"score_spread":0.2555709124946254,"validation_status":"score_only:v0-immature-baseline","note":"Baseline scores from an immature model (maturity gate not passed). Scores rank; they never assert a category."}}