Absolute configuration-dependent epoxide formation from isoflavan-4-ol stereoisomers by biphenyl dioxygenase of Pseudomonas pseudoalcaligenes strain KF707
DC Field | Value | Language |
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dc.contributor.author | Seo, Jiyoung | - |
dc.contributor.author | Kang, Su-Il | - |
dc.contributor.author | Won, Dongho | - |
dc.contributor.author | Kim, Mihyang | - |
dc.contributor.author | Ryu, Ji-Young | - |
dc.contributor.author | Kang, Suk-Woo | - |
dc.contributor.author | Um, Byung-Hun | - |
dc.contributor.author | Pan, Cheol-Ho | - |
dc.contributor.author | Ahn, Joong-Hoon | - |
dc.contributor.author | Chong, Youhoon | - |
dc.contributor.author | Kanaly, Robert A. | - |
dc.contributor.author | Han, Jaehong | - |
dc.contributor.author | Hur, Hor-Gil | - |
dc.date.available | 2019-05-29T13:39:25Z | - |
dc.date.issued | 2011-03 | - |
dc.identifier.issn | 0175-7598 | - |
dc.identifier.issn | 1432-0614 | - |
dc.identifier.uri | https://scholarworks.bwise.kr/cau/handle/2019.sw.cau/21705 | - |
dc.description.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. | - |
dc.format.extent | 10 | - |
dc.language | 영어 | - |
dc.language.iso | ENG | - |
dc.publisher | SPRINGER | - |
dc.title | Absolute configuration-dependent epoxide formation from isoflavan-4-ol stereoisomers by biphenyl dioxygenase of Pseudomonas pseudoalcaligenes strain KF707 | - |
dc.type | Article | - |
dc.identifier.doi | 10.1007/s00253-010-2989-1 | - |
dc.identifier.bibliographicCitation | APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, v.89, no.6, pp 1773 - 1782 | - |
dc.description.isOpenAccess | N | - |
dc.identifier.wosid | 000288333800012 | - |
dc.identifier.scopusid | 2-s2.0-79952573182 | - |
dc.citation.endPage | 1782 | - |
dc.citation.number | 6 | - |
dc.citation.startPage | 1773 | - |
dc.citation.title | APPLIED MICROBIOLOGY AND BIOTECHNOLOGY | - |
dc.citation.volume | 89 | - |
dc.type.docType | Article | - |
dc.publisher.location | 미국 | - |
dc.subject.keywordAuthor | Biphenyl dioxygenase | - |
dc.subject.keywordAuthor | Pseudomonas pseudoalcaligene | - |
dc.subject.keywordAuthor | Isoflavanol epoxide | - |
dc.subject.keywordAuthor | Pterocarpan | - |
dc.subject.keywordAuthor | Medicarpin | - |
dc.subject.keywordPlus | CRYSTAL-STRUCTURE | - |
dc.subject.keywordPlus | ESCHERICHIA-COLI | - |
dc.subject.keywordPlus | B-RING | - |
dc.subject.keywordPlus | PTEROCARPANS | - |
dc.subject.keywordPlus | METABOLISM | - |
dc.subject.keywordPlus | ISOFLAVONE | - |
dc.subject.keywordPlus | CHEMISTRY | - |
dc.subject.keywordPlus | BINDING | - |
dc.subject.keywordPlus | SITE | - |
dc.subject.keywordPlus | CIS | - |
dc.relation.journalResearchArea | Biotechnology & Applied Microbiology | - |
dc.relation.journalWebOfScienceCategory | Biotechnology & Applied Microbiology | - |
dc.description.journalRegisteredClass | sci | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
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