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- Title
Absolute configuration-dependent epoxide formation from isoflavan-4-ol stereoisomers by biphenyl dioxygenase of Pseudomonas pseudoalcaligenes strain KF707.
- Authors
Jiyoung Seo; Su-Il Kang; Dongho Won; Mihyang Kim; Ji-Young Ryu; Suk-Woo Kang; Byung-Hun Um; Cheol-Ho Pan; Joong-Hoon Ahn; Youhoon Chong; Kanaly, Robert A.; Jaehong Han; Hor-Gil Hur
- 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: (3 S,4 S)- cis-isoflavan-4-ol > (3 R,4 S)- trans-isoflavan-4-ol > (3 S,4 R)- trans-isoflavan-4-ol > (3 R,4 R)- 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.
- Subjects
EPOXY compounds; STEREOISOMERS; BIPHENYL compounds; DIOXYS; PSEUDOMONAS
- Publication
Applied Microbiology & Biotechnology, 2011, Vol 89, Issue 6, p1773
- ISSN
0175-7598
- Publication type
Article
- DOI
10.1007/s00253-010-2989-1