Seo, Jiyoung Kang, Su-Il Won, Dongho Kim, Mihyang Ryu, Ji-Young Kang, Suk-Woo Um, Byung-Hun Pan, Cheol-Ho Ahn, Joong-Hoon Chong, Youhoon Kanaly, Robert A. Han, Jaehong Hur, Hor-Gil 2024-01-20T17:32:23Z 2024-01-20T17:32:23Z 2021-09-02 2011-03 0175-7598 https://pubs.kist.re.kr/handle/201004/130591 Biphenyl dioxygenase from Pseudomonas pseudoalcaligenes strain KF707 expressed in Escherichia coli was found to exhibit monooxygenase activity toward four stereoisomers of isoflavan-4-ol. LC-MS and LC-NMR analyses of the metabolites revealed that the corresponding epoxides formed between C2' and C3' on the B-ring of each isoflavan-4-ol substrate were the sole products. The relative reactivity of the stereoisomers was found to be in the order: (3S,4S)-cis-isoflavan-4-ol > (3R,4S)-trans-isoflavan-4-ol > (3S,4R)-trans-isoflavan-4-ol > (3R, 4R)-cis-isoflavan-4-ol and this likely depended upon the absolute configuration of the 4-OH group on the isoflavanols, as explained by an enzyme-substrate docking study. The epoxides produced from isoflavan-4-ols by P. pseudoalcaligenes strain KF707 were further abiotically transformed into pterocarpan, the molecular structure of which is commonly found as part of plant-protective phytoalexins, such as maackiain from Cicer arietinum and medicarpin from Medicago sativa. English SPRINGER CRYSTAL-STRUCTURE ESCHERICHIA-COLI B-RING PTEROCARPANS METABOLISM ISOFLAVONE CHEMISTRY BINDING SITE CIS Absolute configuration-dependent epoxide formation from isoflavan-4-ol stereoisomers by biphenyl dioxygenase of Pseudomonas pseudoalcaligenes strain KF707 Article 10.1007/s00253-010-2989-1 1 APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, v.89, no.6, pp.1773 - 1782 APPLIED MICROBIOLOGY AND BIOTECHNOLOGY 89 6 1773 1782 scie scopus 000288333800012 2-s2.0-79952573182 Biotechnology & Applied Microbiology Biotechnology & Applied Microbiology Article CRYSTAL-STRUCTURE ESCHERICHIA-COLI B-RING PTEROCARPANS METABOLISM ISOFLAVONE CHEMISTRY BINDING SITE CIS Biphenyl dioxygenase Pseudomonas pseudoalcaligene Isoflavanol epoxide Pterocarpan Medicarpin