Absolute configuration-dependent epoxide formation from isoflavan-4-ol stereoisomers by biphenyl dioxygenase of Pseudomonas pseudoalcaligenes strain KF707
- Authors
- 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
- Issue Date
- Mar-2011
- Publisher
- SPRINGER
- Keywords
- Biphenyl dioxygenase; Pseudomonas pseudoalcaligene; Isoflavanol epoxide; Pterocarpan; Medicarpin
- Citation
- APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, v.89, no.6, pp 1773 - 1782
- Pages
- 10
- Journal Title
- APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
- Volume
- 89
- Number
- 6
- Start Page
- 1773
- End Page
- 1782
- URI
- https://scholarworks.bwise.kr/cau/handle/2019.sw.cau/21705
- DOI
- 10.1007/s00253-010-2989-1
- ISSN
- 0175-7598
1432-0614
- Abstract
- 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.
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