{"id":"https://openalex.org/W4399139434","doi":"https://doi.org/10.1021/acs.jcim.4c00640","title":"Origin of Chemoselectivity of Halohydrin Dehalogenase-Catalyzed Epoxide Ring-Opening Reactions","display_name":"Origin of Chemoselectivity of Halohydrin Dehalogenase-Catalyzed Epoxide Ring-Opening Reactions","publication_year":2024,"publication_date":"2024-05-29","ids":{"openalex":"https://openalex.org/W4399139434","doi":"https://doi.org/10.1021/acs.jcim.4c00640","pmid":"https://pubmed.ncbi.nlm.nih.gov/38808649"},"language":"en","primary_location":{"id":"doi:10.1021/acs.jcim.4c00640","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.jcim.4c00640","pdf_url":null,"source":{"id":"https://openalex.org/S167262187","display_name":"Journal of Chemical Information and Modeling","issn_l":"1549-9596","issn":["1549-9596","1549-960X"],"is_oa":false,"is_in_doaj":false,"is_core":true,"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of Chemical Information and Modeling","raw_type":"journal-article"},"type":"article","indexed_in":["crossref","pubmed"],"open_access":{"is_oa":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5075684439","display_name":"Qianqian Wang","orcid":"https://orcid.org/0000-0003-0440-1760"},"institutions":[{"id":"https://openalex.org/I38877650","display_name":"Zhengzhou University","ror":"https://ror.org/04ypx8c21","country_code":"CN","type":"education","lineage":["https://openalex.org/I38877650"]}],"countries":["CN"],"is_corresponding":false,"raw_author_name":"Qian-Qian Wang","raw_affiliation_strings":["College of Chemistry, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, Henan, P. R. China"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"College of Chemistry, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, Henan, P. R. China","institution_ids":["https://openalex.org/I38877650"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5013879765","display_name":"Jinshuai Song","orcid":"https://orcid.org/0000-0002-1909-9253"},"institutions":[{"id":"https://openalex.org/I38877650","display_name":"Zhengzhou University","ror":"https://ror.org/04ypx8c21","country_code":"CN","type":"education","lineage":["https://openalex.org/I38877650"]}],"countries":["CN"],"is_corresponding":true,"raw_author_name":"Jinshuai Song","raw_affiliation_strings":["College of Chemistry, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, Henan, P. R. China"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"College of Chemistry, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, Henan, P. R. China","institution_ids":["https://openalex.org/I38877650"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5071296084","display_name":"Donghui Wei","orcid":"https://orcid.org/0000-0003-2820-282X"},"institutions":[{"id":"https://openalex.org/I38877650","display_name":"Zhengzhou University","ror":"https://ror.org/04ypx8c21","country_code":"CN","type":"education","lineage":["https://openalex.org/I38877650"]}],"countries":["CN"],"is_corresponding":true,"raw_author_name":"Donghui Wei","raw_affiliation_strings":["College of Chemistry, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, Henan, P. R. China"],"raw_orcid":"https://orcid.org/0000-0003-2820-282X","affiliations":[{"raw_affiliation_string":"College of Chemistry, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, Henan, P. R. China","institution_ids":["https://openalex.org/I38877650"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5013879765","https://openalex.org/A5071296084"],"corresponding_institution_ids":["https://openalex.org/I38877650"],"apc_list":null,"apc_paid":null,"fwci":2.4291,"has_fulltext":false,"cited_by_count":13,"citation_normalized_percentile":{"value":0.88851244,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":98,"max":99},"biblio":{"volume":"64","issue":"11","first_page":"4530","last_page":"4541"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T12191","display_name":"Chemical Reaction Mechanisms","score":0.9926000237464905,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},"topics":[{"id":"https://openalex.org/T12191","display_name":"Chemical Reaction Mechanisms","score":0.9926000237464905,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T12915","display_name":"Biochemical Acid Research Studies","score":0.9764999747276306,"subfield":{"id":"https://openalex.org/subfields/1303","display_name":"Biochemistry"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T10044","display_name":"Protein Structure and Dynamics","score":0.9348000288009644,"subfield":{"id":"https://openalex.org/subfields/1312","display_name":"Molecular Biology"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/chemoselectivity","display_name":"Chemoselectivity","score":0.9651755094528198},{"id":"https://openalex.org/keywords/epoxide","display_name":"Epoxide","score":0.8662190437316895},{"id":"https://openalex.org/keywords/chemistry","display_name":"Chemistry","score":0.7438256740570068},{"id":"https://openalex.org/keywords/nucleophile","display_name":"Nucleophile","score":0.6800910234451294},{"id":"https://openalex.org/keywords/electrophile","display_name":"Electrophile","score":0.6536957621574402},{"id":"https://openalex.org/keywords/transition-state","display_name":"Transition state","score":0.5875100493431091},{"id":"https://openalex.org/keywords/ring","display_name":"Ring (chemistry)","score":0.5088603496551514},{"id":"https://openalex.org/keywords/stereochemistry","display_name":"Stereochemistry","score":0.421329528093338},{"id":"https://openalex.org/keywords/catalysis","display_name":"Catalysis","score":0.4183204770088196},{"id":"https://openalex.org/keywords/combinatorial-chemistry","display_name":"Combinatorial chemistry","score":0.3847827911376953},{"id":"https://openalex.org/keywords/computational-chemistry","display_name":"Computational chemistry","score":0.3694097101688385},{"id":"https://openalex.org/keywords/organic-chemistry","display_name":"Organic chemistry","score":0.19920608401298523}],"concepts":[{"id":"https://openalex.org/C190667039","wikidata":"https://www.wikidata.org/wiki/Q3738104","display_name":"Chemoselectivity","level":3,"score":0.9651755094528198},{"id":"https://openalex.org/C2776920199","wikidata":"https://www.wikidata.org/wiki/Q408028","display_name":"Epoxide","level":3,"score":0.8662190437316895},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.7438256740570068},{"id":"https://openalex.org/C178907741","wikidata":"https://www.wikidata.org/wiki/Q745930","display_name":"Nucleophile","level":3,"score":0.6800910234451294},{"id":"https://openalex.org/C50027330","wikidata":"https://www.wikidata.org/wiki/Q908086","display_name":"Electrophile","level":3,"score":0.6536957621574402},{"id":"https://openalex.org/C89031862","wikidata":"https://www.wikidata.org/wiki/Q906964","display_name":"Transition state","level":3,"score":0.5875100493431091},{"id":"https://openalex.org/C2780378348","wikidata":"https://www.wikidata.org/wiki/Q25351438","display_name":"Ring (chemistry)","level":2,"score":0.5088603496551514},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.421329528093338},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.4183204770088196},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.3847827911376953},{"id":"https://openalex.org/C147597530","wikidata":"https://www.wikidata.org/wiki/Q369472","display_name":"Computational chemistry","level":1,"score":0.3694097101688385},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.19920608401298523}],"mesh":[{"descriptor_ui":"D004852","descriptor_name":"Epoxy Compounds","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":true},{"descriptor_ui":"D004852","descriptor_name":"Epoxy Compounds","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":true},{"descriptor_ui":"D004852","descriptor_name":"Epoxy Compounds","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":true},{"descriptor_ui":"D004852","descriptor_name":"Epoxy Compounds","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D004852","descriptor_name":"Epoxy Compounds","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D004852","descriptor_name":"Epoxy Compounds","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D006867","descriptor_name":"Hydrolases","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":true},{"descriptor_ui":"D006867","descriptor_name":"Hydrolases","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":true},{"descriptor_ui":"D006867","descriptor_name":"Hydrolases","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":true},{"descriptor_ui":"D006867","descriptor_name":"Hydrolases","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D006867","descriptor_name":"Hydrolases","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D006867","descriptor_name":"Hydrolases","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D011789","descriptor_name":"Quantum Theory","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D011789","descriptor_name":"Quantum Theory","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D011789","descriptor_name":"Quantum Theory","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D013379","descriptor_name":"Substrate Specificity","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D013379","descriptor_name":"Substrate Specificity","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D013379","descriptor_name":"Substrate Specificity","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D020134","descriptor_name":"Catalytic Domain","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D020134","descriptor_name":"Catalytic Domain","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D020134","descriptor_name":"Catalytic Domain","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D055162","descriptor_name":"Biocatalysis","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D055162","descriptor_name":"Biocatalysis","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D055162","descriptor_name":"Biocatalysis","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D056004","descriptor_name":"Molecular Dynamics Simulation","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D056004","descriptor_name":"Molecular Dynamics Simulation","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D056004","descriptor_name":"Molecular Dynamics Simulation","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/acs.jcim.4c00640","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.jcim.4c00640","pdf_url":null,"source":{"id":"https://openalex.org/S167262187","display_name":"Journal of Chemical Information and Modeling","issn_l":"1549-9596","issn":["1549-9596","1549-960X"],"is_oa":false,"is_in_doaj":false,"is_core":true,"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of Chemical Information and Modeling","raw_type":"journal-article"},{"id":"pmid:38808649","is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/38808649","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of chemical information and modeling","raw_type":null}],"best_oa_location":null,"sustainable_development_goals":[{"display_name":"Affordable and clean energy","id":"https://metadata.un.org/sdg/7","score":0.800000011920929}],"awards":[{"id":"https://openalex.org/G1047009805","display_name":null,"funder_award_id":"D20003","funder_id":"https://openalex.org/F4320327912","funder_display_name":"Higher Education Discipline Innovation Project"},{"id":"https://openalex.org/G3633289736","display_name":null,"funder_award_id":"JC23261010","funder_id":"https://openalex.org/F4320322766","funder_display_name":"Zhengzhou University"},{"id":"https://openalex.org/G5160519804","display_name":"\u4e0d\u542b\u91d1\u5c5e\u548c\u8f85\u56e0\u5b50\u7684\u6c27\u5316\u9176\u548c\u52a0\u6c27\u9176\u50ac\u5316\u53cd\u5e94\u673a\u7406\u7684\u7406\u8bba\u7814\u7a76","funder_award_id":"21773214","funder_id":"https://openalex.org/F4320321001","funder_display_name":"National Natural Science Foundation of China"}],"funders":[{"id":"https://openalex.org/F4320321001","display_name":"National Natural Science Foundation of China","ror":"https://ror.org/01h0zpd94"},{"id":"https://openalex.org/F4320322766","display_name":"Zhengzhou University","ror":"https://ror.org/04ypx8c21"},{"id":"https://openalex.org/F4320327912","display_name":"Higher Education Discipline Innovation Project","ror":null}],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":66,"referenced_works":["https://openalex.org/W1820968952","https://openalex.org/W1964535362","https://openalex.org/W1964567061","https://openalex.org/W1969253962","https://openalex.org/W1976499671","https://openalex.org/W1979530725","https://openalex.org/W1981263132","https://openalex.org/W1982703140","https://openalex.org/W1988091937","https://openalex.org/W1988485815","https://openalex.org/W1995134421","https://openalex.org/W1999527055","https://openalex.org/W2007438820","https://openalex.org/W2008423326","https://openalex.org/W2011215428","https://openalex.org/W2023271753","https://openalex.org/W2023349989","https://openalex.org/W2025396755","https://openalex.org/W2029667189","https://openalex.org/W2038442918","https://openalex.org/W2042616927","https://openalex.org/W2045076985","https://openalex.org/W2051434435","https://openalex.org/W2052559859","https://openalex.org/W2057980421","https://openalex.org/W2064969177","https://openalex.org/W2067718414","https://openalex.org/W2068358349","https://openalex.org/W2075223650","https://openalex.org/W2083994071","https://openalex.org/W2092157292","https://openalex.org/W2094941054","https://openalex.org/W2105055623","https://openalex.org/W2110872379","https://openalex.org/W2112850441","https://openalex.org/W2117458899","https://openalex.org/W2129300174","https://openalex.org/W2134967712","https://openalex.org/W2143981217","https://openalex.org/W2147993766","https://openalex.org/W2151449293","https://openalex.org/W2171830166","https://openalex.org/W2313116527","https://openalex.org/W2404070135","https://openalex.org/W2404280981","https://openalex.org/W2511523112","https://openalex.org/W2613905013","https://openalex.org/W2625904587","https://openalex.org/W2736178248","https://openalex.org/W2739439285","https://openalex.org/W2769904338","https://openalex.org/W2936033307","https://openalex.org/W3034310241","https://openalex.org/W3036997165","https://openalex.org/W3138679836","https://openalex.org/W3217119681","https://openalex.org/W4214944872","https://openalex.org/W4220694746","https://openalex.org/W4283831563","https://openalex.org/W4286209780","https://openalex.org/W4312064869","https://openalex.org/W4312193366","https://openalex.org/W4323057229","https://openalex.org/W4379932196","https://openalex.org/W4385330829","https://openalex.org/W4388724287"],"related_works":["https://openalex.org/W2111978725","https://openalex.org/W2051290316","https://openalex.org/W1954521139","https://openalex.org/W2100457900","https://openalex.org/W1893761061","https://openalex.org/W2949091273","https://openalex.org/W2049917615","https://openalex.org/W2949551219","https://openalex.org/W1997700499","https://openalex.org/W2046236137"],"abstract_inverted_index":{"By":[0],"performing":[1],"molecular":[2],"dynamics":[3],"(MD),":[4],"quantum":[5],"mechanical/molecular":[6],"mechanical":[7],"(QM/MM)":[8],"calculations,":[9,13],"and":[10,42,69,97,130,161],"QM":[11],"cluster":[12],"the":[14,27,43,48,52,56,101,104,108,116,121,156],"origin":[15],"of":[16,18,24,59,74,103,107,120,159],"chemoselectivity":[17],"halohydrin":[19],"dehalogenase":[20],"(HHDH)-catalyzed":[21],"ring-opening":[22,165],"reactions":[23,166],"epoxide":[25,60,109,164],"with":[26,51,143,167],"nucleophilic":[28,53],"reagent":[29],"NO":[30,62],"2":[31,63],"\u2212":[32,64],"has":[33,70],"been":[34],"explored.":[35],"Four":[36],"possible":[37],"chemoselective":[38,122],"pathways":[39],"were":[40,140],"considered,":[41],"computed":[44],"results":[45],"indicate":[46],"that":[47],"pathway":[49],"associated":[50],"attack":[54],"on":[55],"C\u03b1":[57],"position":[58],"by":[61,93],"is":[65,78],"most":[66],"energetically":[67],"favorable":[68],"an":[71,146],"energy":[72,117],"barrier":[73,118],"12.9":[75],"kcal/mol,":[76],"which":[77],"close":[79],"to":[80,111],"14.1":[81],"kcal/mol":[82],"derived":[83],"from":[84],"experimental":[85],"kinetic":[86],"data.":[87],"A":[88],"hydrogen":[89],"bonding":[90],"network":[91],"formed":[92],"residues":[94],"Ser140,":[95],"Tyr153,":[96],"Arg157":[98],"can":[99],"strengthen":[100],"electrophilicity":[102],"active":[105],"site":[106],"substrate":[110],"affect":[112],"chemoselectivity.":[113,169],"To":[114],"predict":[115],"trends":[119],"transition":[123],"states,":[124],"multiple":[125],"analyses":[126],"including":[127],"distortion":[128],"analysis":[129,139],"electrophilic":[131],"Parr":[132],"function":[133],"(":[134],"P":[135],"k":[136],"+":[137],")":[138],"carried":[141],"out":[142],"or":[144],"without":[145],"enzyme":[147],"environment.":[148],"The":[149],"obtained":[150],"insights":[151],"should":[152],"be":[153],"valuable":[154],"for":[155],"rational":[157],"design":[158],"enzyme-catalyzed":[160],"biomimetic":[162],"organocatalytic":[163],"special":[168]},"counts_by_year":[{"year":2026,"cited_by_count":3},{"year":2025,"cited_by_count":10}],"updated_date":"2026-07-27T08:26:11.824852","created_date":"2025-10-10T00:00:00"}
