{"id":"W2037344831","doi":"10.1021/jo9003458","title":"Intramolecular Hydrogen Bond-Controlled Prolyl Amide Isomerization in Glucosyl 3′(<i>S</i>)-Hydroxy-5′-hydroxymethylproline Hybrids: Influence of a <i>C</i>-5′-Hydroxymethyl Substituent on the Thermodynamics and Kinetics of Prolyl Amide <i>Cis</i>/<i>Trans</i> Isomerization","year":2009,"lang":"en","type":"article","venue":"The Journal of Organic Chemistry","topic":"Chemical Synthesis and Analysis","field":"Biochemistry, Genetics and Molecular Biology","cited_by":19,"is_retracted":false,"has_abstract":true,"ca_institutions":"University of Manitoba; University of Lethbridge","funders":"Natural Sciences and Engineering Research Council of Canada","keywords":"Chemistry; Substituent; Isomerization; Stereochemistry; Hydroxymethyl; Amide; Intramolecular force; Hydrogen bond; Population; Epimer; Molecule; Organic chemistry; Catalysis","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":"codex-gemma-dda1882f352a","candidate_categories":["metaepi_narrow"],"consensus_categories":[],"category_scores_codex":[0.0009589982,0.0003814459,0.0008039885,0.00007897579,0.0000589273,0.00002424462,0.0006723551,0.0002277171,0.00002319604],"category_scores_gemma":[0.0006410038,0.000249422,0.0002971371,0.0005589439,0.0003000085,0.00002156222,0.00007683037,0.00040272,3.893903e-7],"about_ca_system_candidate":false,"about_ca_system_consensus":false,"about_ca_system_score_codex":0.00005040233,"about_ca_system_score_gemma":0.0001119007,"about_ca_topic_candidate":false,"about_ca_topic_consensus":false,"about_ca_topic_score_codex":0.00001233676,"about_ca_topic_score_gemma":0.00000704581,"domain_scores_codex":[0.99726,0.0001720214,0.001369042,0.0003180667,0.0005530314,0.0003278722],"domain_scores_gemma":[0.9975613,0.000169679,0.00127465,0.0006022709,0.0002762145,0.0001159118],"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":[0.001046599,0.0004227856,0.0002539284,0.00007235095,0.000213951,0.000004962998,0.000149207,0.004315683,0.9929647,0.00001072878,0.00001043107,0.0005346148],"study_design_scores_gemma":[0.002267581,0.0003919716,0.0004534836,0.0001761947,0.0003514339,0.00006695546,0.00006706519,0.001230197,0.9942878,0.0003886277,0.0000757083,0.0002430211],"study_design_candidate":"bench_or_experimental","study_design_consensus":"bench_or_experimental","genre_codex":"empirical","genre_gemma":"empirical","genre_scores_codex":[0.9938412,0.002255061,0.00230411,0.001013045,0.00001711544,0.0004206697,0.00002038702,0.000006908045,0.0001214621],"genre_scores_gemma":[0.9970227,0.002243452,0.0001256125,0.0003940263,0.0001143386,0.000008180868,0.00002665885,0.00003941339,0.00002555324],"genre_candidate":"empirical","genre_consensus":"empirical","teacher_disagreement_score":0.003181523,"threshold_uncertainty_score":0.9999958,"prediction_status":"machine_predicted_unvalidated"},"machine_scores":{"provisional":true,"baseline":true,"maturity_gate_passed":false,"score_opus":0.002993907729903618,"score_gpt":0.1946413305898451,"score_spread":0.1916474228599415,"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."}}