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PLRs are downstream of dirigent protein engendered, coniferyl alcohol derived, stereoselective coupling to afford entry into the 8\u2010 and 8\u2032\u2010linked furofuran lignan, pinoresinol. Our investigations showed that each PLR homolog can enantiospecifically metabolize different furofuran lignans with modified aromatic ring substituents, but where phenolic groups at both C4\/C4\u2032 are essential for catalysis. These results are consistent with quinone methide intermediate formation in the PLR active site. Site\u2010directed mutagenesis and kinetic measurements provided additional insight into factors affecting enantioselectivity and kinetic properties. From these data, PLRs can be envisaged to allow for the biotechnological potential of generation of various lignan skeleta, that could be differentially \u201cdecorated\u201d on their aromatic ring substituents, via the action of upstream dirigent proteins.<\/jats:p>","DOI":"10.1002\/chir.23218","type":"journal-article","created":{"date-parts":[[2020,3,23]],"date-time":"2020-03-23T07:14:38Z","timestamp":1584947678000},"page":"770-789","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Pinoresinol\u2010lariciresinol reductase: Substrate versatility, enantiospecificity, and kinetic properties"],"prefix":"10.1002","volume":"32","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9222-1729","authenticated-orcid":false,"given":"Julianne K.","family":"Hwang","sequence":"first","affiliation":[{"name":"Institute of Biological Chemistry Washington State University  Pullman Washington"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9907-416X","authenticated-orcid":false,"given":"Syed G.A.","family":"Moinuddin","sequence":"additional","affiliation":[{"name":"Institute of Biological Chemistry Washington State University  Pullman Washington"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3248-6485","authenticated-orcid":false,"given":"Laurence B.","family":"Davin","sequence":"additional","affiliation":[{"name":"Institute of Biological Chemistry Washington State University  Pullman Washington"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5742-032X","authenticated-orcid":false,"given":"Norman G.","family":"Lewis","sequence":"additional","affiliation":[{"name":"Institute of Biological Chemistry Washington State University  Pullman Washington"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2020,3,23]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/bk-1998-0697.ch025"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.274.11.7516"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1139\/v59-246"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1139\/v60-324"},{"issue":"5","key":"e_1_2_6_6_1","first-page":"1094","article-title":"Occupational asthma and rhinitis due to western red cedar (Thuja plicata)","volume":"108","author":"Chan\u2010Yeung M","year":"1973","journal-title":"Am Rev Respir Dis"},{"key":"e_1_2_6_7_1","first-page":"505","volume-title":"Asthma in the Workplace","author":"Chan\u2010Yeung M","year":"2006"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1081-1206(10)62888-8"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr200325f"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.2165\/00002018-200629030-00005"},{"key":"e_1_2_6_11_1","first-page":"1","article-title":"The search for anticancer agents from tropical plants","volume":"107","author":"Henkin JM","year":"2018","journal-title":"Prog Chem Org Nat Prod"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.275.5298.362"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.copbio.2005.06.010"},{"key":"e_1_2_6_14_1","volume-title":"The Lignan Handbook with CD\u2010ROM","author":"Davin LB","year":"2020"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.271.46.29473"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.274.2.618"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1039\/b516563f"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M008622200"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M413266200"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M112.400689"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0031-9422(00)00242-9"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.aac7202"},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b10717"},{"key":"e_1_2_6_24_1","volume-title":"The Lignan Handbook with CD\u2010ROM","author":"Lewis NG","year":"2020"},{"key":"e_1_2_6_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/B978-008045382-8.00001-0"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/0031-9422(83)80235-0"},{"key":"e_1_2_6_27_1","first-page":"324","article-title":"Phenolic compounds from Forsythia leaves. 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