{"id":"https://openalex.org/W2066201640","doi":"https://doi.org/10.1021/op9002714","title":"Highly Enantioselective Reduction of a Small Heterocyclic Ketone: Biocatalytic Reduction of Tetrahydrothiophene-3-one to the Corresponding (R)-Alcohol","display_name":"Highly Enantioselective Reduction of a Small Heterocyclic Ketone: Biocatalytic Reduction of Tetrahydrothiophene-3-one to the Corresponding (R)-Alcohol","publication_year":2009,"publication_date":"2009-12-01","ids":{"openalex":"https://openalex.org/W2066201640","doi":"https://doi.org/10.1021/op9002714","mag":"2066201640"},"language":"en","primary_location":{"id":"doi:10.1021/op9002714","doi":"https://doi.org/10.1021/op9002714","is_oa":false,"landing_page_url":"https://doi.org/10.1021/op9002714","pdf_url":null,"source":{"id":"https://openalex.org/S107255770","display_name":"Organic Process Research & Development","issn_l":"1083-6160","issn":["1083-6160","1520-586X"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-b","jufo-1","norway-1","poland-100","russia-white-list-1","vabb-shw"],"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":"Organic Process Research & Development","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"indexed_in":["crossref"],"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/A5111715896","display_name":"Jack Liang","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I175381709","display_name":"Codexis (United States)","ror":"https://ror.org/00f76ab84","country_code":"US","type":"company","lineage":["https://openalex.org/I175381709"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Jack Liang","raw_affiliation_strings":["Codexis, Inc., 200 Penobscot Drive, Redwood City, California 94063, U.S.A., and Pfizer Global R&D, Easten Point Road, Groton, Connecticut 06340, U.S.A"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Codexis, Inc., 200 Penobscot Drive, Redwood City, California 94063, U.S.A., and Pfizer Global R&D, Easten Point Road, Groton, Connecticut 06340, U.S.A","institution_ids":["https://openalex.org/I175381709"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5021044397","display_name":"Emily C. Mundorff","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I175381709","display_name":"Codexis (United States)","ror":"https://ror.org/00f76ab84","country_code":"US","type":"company","lineage":["https://openalex.org/I175381709"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Emily Mundorff","raw_affiliation_strings":["Codexis, Inc., 200 Penobscot Drive, Redwood City, California 94063, U.S.A., and Pfizer Global R&D, Easten Point Road, Groton, Connecticut 06340, U.S.A"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Codexis, Inc., 200 Penobscot Drive, Redwood City, California 94063, U.S.A., and Pfizer Global R&D, Easten Point Road, Groton, Connecticut 06340, U.S.A","institution_ids":["https://openalex.org/I175381709"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5055095436","display_name":"Rama Voladri","orcid":"https://orcid.org/0000-0003-3329-6429","observed_orcids":["https://orcid.org/0000-0003-3329-6429"]},"institutions":[{"id":"https://openalex.org/I175381709","display_name":"Codexis (United States)","ror":"https://ror.org/00f76ab84","country_code":"US","type":"company","lineage":["https://openalex.org/I175381709"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Rama Voladri","raw_affiliation_strings":["Codexis, Inc., 200 Penobscot Drive, Redwood City, California 94063, U.S.A., and Pfizer Global R&D, Easten Point Road, Groton, Connecticut 06340, U.S.A"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Codexis, Inc., 200 Penobscot Drive, Redwood City, California 94063, U.S.A., and Pfizer Global R&D, Easten Point Road, Groton, Connecticut 06340, U.S.A","institution_ids":["https://openalex.org/I175381709"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5020561904","display_name":"Stephan Jenne","orcid":"https://orcid.org/0000-0002-3269-2190","observed_orcids":["https://orcid.org/0000-0002-3269-2190"]},"institutions":[{"id":"https://openalex.org/I175381709","display_name":"Codexis (United States)","ror":"https://ror.org/00f76ab84","country_code":"US","type":"company","lineage":["https://openalex.org/I175381709"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Stephan Jenne","raw_affiliation_strings":["Codexis, Inc., 200 Penobscot Drive, Redwood City, California 94063, U.S.A., and Pfizer Global R&D, Easten Point Road, Groton, Connecticut 06340, U.S.A"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Codexis, Inc., 200 Penobscot Drive, Redwood City, California 94063, U.S.A., and Pfizer Global R&D, Easten Point Road, Groton, Connecticut 06340, U.S.A","institution_ids":["https://openalex.org/I175381709"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5036034290","display_name":"Lynne Gilson","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I175381709","display_name":"Codexis (United States)","ror":"https://ror.org/00f76ab84","country_code":"US","type":"company","lineage":["https://openalex.org/I175381709"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Lynne Gilson","raw_affiliation_strings":["Codexis, Inc., 200 Penobscot Drive, Redwood City, California 94063, U.S.A., and Pfizer Global R&D, Easten Point Road, Groton, Connecticut 06340, U.S.A"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Codexis, Inc., 200 Penobscot Drive, Redwood City, California 94063, U.S.A., and Pfizer Global R&D, Easten Point Road, Groton, Connecticut 06340, U.S.A","institution_ids":["https://openalex.org/I175381709"]}]},{"author_position":"middle","author":{"id":null,"display_name":"Aaron Conway","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I175381709","display_name":"Codexis (United States)","ror":"https://ror.org/00f76ab84","country_code":"US","type":"company","lineage":["https://openalex.org/I175381709"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Aaron Conway","raw_affiliation_strings":["Codexis, Inc., 200 Penobscot Drive, Redwood City, California 94063, U.S.A., and Pfizer Global R&D, Easten Point Road, Groton, Connecticut 06340, U.S.A"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Codexis, Inc., 200 Penobscot Drive, Redwood City, California 94063, U.S.A., and Pfizer Global R&D, Easten Point Road, Groton, Connecticut 06340, U.S.A","institution_ids":["https://openalex.org/I175381709"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5044134124","display_name":"Anke Krebber","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I175381709","display_name":"Codexis (United States)","ror":"https://ror.org/00f76ab84","country_code":"US","type":"company","lineage":["https://openalex.org/I175381709"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Anke Krebber","raw_affiliation_strings":["Codexis, Inc., 200 Penobscot Drive, Redwood City, California 94063, U.S.A., and Pfizer Global R&D, Easten Point Road, Groton, Connecticut 06340, U.S.A"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Codexis, Inc., 200 Penobscot Drive, Redwood City, California 94063, U.S.A., and Pfizer Global R&D, Easten Point Road, Groton, Connecticut 06340, U.S.A","institution_ids":["https://openalex.org/I175381709"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5109126905","display_name":"John W. Wong","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I175381709","display_name":"Codexis (United States)","ror":"https://ror.org/00f76ab84","country_code":"US","type":"company","lineage":["https://openalex.org/I175381709"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"John Wong","raw_affiliation_strings":["Codexis, Inc., 200 Penobscot Drive, Redwood City, California 94063, U.S.A., and Pfizer Global R&D, Easten Point Road, Groton, Connecticut 06340, U.S.A"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Codexis, Inc., 200 Penobscot Drive, Redwood City, California 94063, U.S.A., and Pfizer Global R&D, Easten Point Road, Groton, Connecticut 06340, U.S.A","institution_ids":["https://openalex.org/I175381709"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5013003433","display_name":"Gjalt W. Huisman","orcid":"https://orcid.org/0000-0003-1955-1120","observed_orcids":["https://orcid.org/0000-0003-1955-1120"]},"institutions":[{"id":"https://openalex.org/I175381709","display_name":"Codexis (United States)","ror":"https://ror.org/00f76ab84","country_code":"US","type":"company","lineage":["https://openalex.org/I175381709"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Gjalt Huisman","raw_affiliation_strings":["Codexis, Inc., 200 Penobscot Drive, Redwood City, California 94063, U.S.A., and Pfizer Global R&D, Easten Point Road, Groton, Connecticut 06340, U.S.A"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Codexis, Inc., 200 Penobscot Drive, Redwood City, California 94063, U.S.A., and Pfizer Global R&D, Easten Point Road, Groton, Connecticut 06340, U.S.A","institution_ids":["https://openalex.org/I175381709"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5076786341","display_name":"SUSAN J. TRUESDELL","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I175381709","display_name":"Codexis (United States)","ror":"https://ror.org/00f76ab84","country_code":"US","type":"company","lineage":["https://openalex.org/I175381709"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Susan Truesdell","raw_affiliation_strings":["Codexis, Inc., 200 Penobscot Drive, Redwood City, California 94063, U.S.A., and Pfizer Global R&D, Easten Point Road, Groton, Connecticut 06340, U.S.A"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Codexis, Inc., 200 Penobscot Drive, Redwood City, California 94063, U.S.A., and Pfizer Global R&D, Easten Point Road, Groton, Connecticut 06340, U.S.A","institution_ids":["https://openalex.org/I175381709"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5071687972","display_name":"James Joseph Lalonde","orcid":"https://orcid.org/0000-0003-3027-3555","observed_orcids":["https://orcid.org/0000-0003-3027-3555"]},"institutions":[{"id":"https://openalex.org/I175381709","display_name":"Codexis (United States)","ror":"https://ror.org/00f76ab84","country_code":"US","type":"company","lineage":["https://openalex.org/I175381709"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"James Lalonde","raw_affiliation_strings":["Codexis, Inc., 200 Penobscot Drive, Redwood City, California 94063, U.S.A., and Pfizer Global R&D, Easten Point Road, Groton, Connecticut 06340, U.S.A"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Codexis, Inc., 200 Penobscot Drive, Redwood City, California 94063, U.S.A., and Pfizer Global R&D, Easten Point Road, Groton, Connecticut 06340, U.S.A","institution_ids":["https://openalex.org/I175381709"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5111715896"],"corresponding_institution_ids":["https://openalex.org/I175381709"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":3.2963,"has_fulltext":false,"cited_by_count":133,"citation_normalized_percentile":{"value":0.93486738,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":95,"max":100},"biblio":{"volume":"14","issue":"1","first_page":"188","last_page":"192"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10404","display_name":"Enzyme Catalysis and Immobilization","score":0.9994999766349792,"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"}},"topics":[{"id":"https://openalex.org/T10404","display_name":"Enzyme Catalysis and Immobilization","score":0.9994999766349792,"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"}},{"id":"https://openalex.org/T11281","display_name":"Asymmetric Hydrogenation and Catalysis","score":0.00039999998989515007,"subfield":{"id":"https://openalex.org/subfields/1604","display_name":"Inorganic 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/T10013","display_name":"Asymmetric Synthesis and Catalysis","score":9.999999747378752e-05,"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"}}],"keywords":[{"id":"https://openalex.org/keywords/asymmetric-reduction","display_name":"asymmetric reduction","score":0.9020000100135803},{"id":"https://openalex.org/keywords/enzyme-evolution","display_name":"enzyme evolution","score":0.8500000238418579},{"id":"https://openalex.org/keywords/heterocyclic-ketones","display_name":"heterocyclic ketones","score":0.7950000166893005},{"id":"https://openalex.org/keywords/chiral-alcohols","display_name":"chiral alcohols","score":0.7139999866485596},{"id":"https://openalex.org/keywords/biocatalysis","display_name":"biocatalysis","score":0.7689999938011169},{"id":"https://openalex.org/keywords/asymmetric-biocatalysis","display_name":"asymmetric biocatalysis","score":0.5920000076293945},{"id":"https://openalex.org/keywords/process-scale-up","display_name":"process scale-up","score":0.5720000267028809}],"concepts":[{"id":"https://openalex.org/C2780477052","wikidata":"https://www.wikidata.org/wiki/Q412118","display_name":"Tetrahydrothiophene","level":2,"score":0.9833037853240967},{"id":"https://openalex.org/C2777738585","wikidata":"https://www.wikidata.org/wiki/Q170744","display_name":"Ketone","level":2,"score":0.8108655214309692},{"id":"https://openalex.org/C146686406","wikidata":"https://www.wikidata.org/wiki/Q898628","display_name":"Enantioselective synthesis","level":3,"score":0.790473461151123},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.713308572769165},{"id":"https://openalex.org/C2781066024","wikidata":"https://www.wikidata.org/wiki/Q156","display_name":"Alcohol","level":2,"score":0.6146849393844604},{"id":"https://openalex.org/C191503008","wikidata":"https://www.wikidata.org/wiki/Q16007026","display_name":"Biocatalysis","level":4,"score":0.539406418800354},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.4468909502029419},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.35002946853637695},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.320105642080307},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.2594793140888214},{"id":"https://openalex.org/C65024703","wikidata":"https://www.wikidata.org/wiki/Q373406","display_name":"Reaction mechanism","level":3,"score":0.0801590085029602}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.1021/op9002714","doi":"https://doi.org/10.1021/op9002714","is_oa":false,"landing_page_url":"https://doi.org/10.1021/op9002714","pdf_url":null,"source":{"id":"https://openalex.org/S107255770","display_name":"Organic Process Research & Development","issn_l":"1083-6160","issn":["1083-6160","1520-586X"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-b","jufo-1","norway-1","poland-100","russia-white-list-1","vabb-shw"],"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":"Organic Process Research & Development","raw_type":"journal-article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[{"id":"https://openalex.org/F4320307765","display_name":"Pfizer","ror":"https://ror.org/01xdqrp08"}],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":32,"referenced_works":["https://openalex.org/W1972205391","https://openalex.org/W1976547627","https://openalex.org/W1977249481","https://openalex.org/W1978213633","https://openalex.org/W1986768557","https://openalex.org/W1987206719","https://openalex.org/W1989160593","https://openalex.org/W1989389277","https://openalex.org/W1992145785","https://openalex.org/W2014701110","https://openalex.org/W2019619659","https://openalex.org/W2023819168","https://openalex.org/W2029206307","https://openalex.org/W2034324018","https://openalex.org/W2038364394","https://openalex.org/W2044093594","https://openalex.org/W2045124109","https://openalex.org/W2053497671","https://openalex.org/W2089104282","https://openalex.org/W2089896770","https://openalex.org/W2097674466","https://openalex.org/W2102821582","https://openalex.org/W2132372489","https://openalex.org/W2156414311","https://openalex.org/W2156454061","https://openalex.org/W2156904294","https://openalex.org/W2315607041","https://openalex.org/W2322578805","https://openalex.org/W2950074098","https://openalex.org/W2951925237","https://openalex.org/W2953364043","https://openalex.org/W4240955781"],"related_works":["https://openalex.org/W4404370561","https://openalex.org/W2253084053","https://openalex.org/W2064474303","https://openalex.org/W2085561136","https://openalex.org/W2103252368","https://openalex.org/W3163253884","https://openalex.org/W1595707286","https://openalex.org/W3130479692","https://openalex.org/W4280559882","https://openalex.org/W16047902"],"abstract_inverted_index":{"By":[0],"leveraging":[1],"enzyme":[2],"evolution":[3],"technologies,":[4],"the":[5,12,42,49],"enantioselectivity":[6],"of":[7],"a":[8,37],"KetoREDuctase":[9],"(KRED)":[10],"towards":[11],"nearly":[13],"spatially":[14],"symmetrical":[15],"ketone":[16],"tetrahydrothiophene-3-one":[17],"was":[18],"increased":[19],"from":[20,36,48],"63%":[21],"ee":[22],"to":[23,59],"99.3%":[24],"ee.":[25],"The":[26,52],"biocatalytic":[27,53],"process":[28,54],"gives":[29],"(":[30],"R":[31],")-tetrahydrothiophene-3-ol":[32],"in":[33],"one":[34],"step":[35],"commodity":[38],"chemical":[39],"and":[40],"supplants":[41],"original":[43],"multistep":[44],"hazardous":[45],"processes":[46],"starting":[47],"chiral":[50],"pool.":[51],"has":[55],"been":[56],"successfully":[57],"scaled":[58],"100":[60],"kg.":[61]},"counts_by_year":[{"year":2026,"cited_by_count":2},{"year":2025,"cited_by_count":4},{"year":2024,"cited_by_count":3},{"year":2023,"cited_by_count":6},{"year":2022,"cited_by_count":5},{"year":2021,"cited_by_count":8},{"year":2020,"cited_by_count":10},{"year":2019,"cited_by_count":6},{"year":2018,"cited_by_count":4},{"year":2017,"cited_by_count":11},{"year":2016,"cited_by_count":12},{"year":2015,"cited_by_count":10},{"year":2014,"cited_by_count":12},{"year":2013,"cited_by_count":10},{"year":2012,"cited_by_count":18}],"updated_date":"2026-11-04T10:54:05.112534","created_date":"2016-06-24T00:00:00"}