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Cis-dihydrodiol production on flavone B-ring by biphenyl dioxygenase from pseudomonas pseudoalcaligenes KF707 expressed in escherichia coli
E. coli에서 발현된 Pseudomonas pseudoalcaligenes KF707의 biphenyl dioxygenase에 의한 flavone B-ring의 Cis-dihydrodiol 생산

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Authors
김송영
Advisor
김수일
Issue Date
2003
Publisher
서울대학교 대학원
Keywords
BacteriaBiotransformationCis-DihydrodiolDioxygenaseFlavone
Description
Thesis (master`s)--서울대학교 대학원 :농생명공학부,2003.
Abstract
Escherichia coli JM109 expressing either toluene dioxygenase from Pseudomonas
putida F1 or biphenyl dioxygenase from Pseudomonas pseudoalcaligenes KF707 were
examined for their ability to catalyze flavones. Metabolites from flavone and
5,7-dihydroxyflavone were shown on the HPLC chromatogram, which were not found
in the control experiments. However, 6,7-, 7,8-, 2¡¯,3¡¯-, 3¡¯,4¡¯-, 5,4¡¯-
dihydroxyflavone, 5,6,7-trihydroxyflavone, 5-hydroxy -7-methoxy flavone, and 8-
hydroxy-7-methoxyflavone were not catalyzed by both enzymes. The maximum UVvisible
absorbance for the metabolites from flavone and 5,7-dihydroxyflavone was
found at 337 and 348 nm respectively by the photodiode array detector equipped
in the HPLC. Liquid chromatography/mass spectroscopy (LC/MS) showed 257 and 289
m/z [M + H]+ for the metabolites, respectively. The metabolite of flavone, which
was isolated and purified from the bacterial culture, was further subjected to
analysis of the 1H and 13C nuclear magnetic resonance (NMR) spectroscopy. Based
on the LC/MS and NMR results, biphenyl dioxygenase inserted oxygen at C2¡¯, and
C3¡¯ on the B-ring of flavone, resulting in the formation of flavone cisdihydrodiol
(2-[3,4-dihydroxy-1.5-cyclohexadienyl]-4H-chromen-4-one). Since the
product is not found in Chemical Abstracts, this compound is considered a novel
one. In addition, biotransformation of flavones by biphenyl dioxygenase
suggested a potential role of bacterial dioxygenase able to synthesize noble
compounds from plant secondary metabolites.
Language
English
URI
http://dcollection.snu.ac.kr:80/jsp/common/DcLoOrgPer.jsp?sItemId=000000058214

http://hdl.handle.net/10371/68514
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College of Agriculture and Life Sciences (농업생명과학대학)Dept. of Food and Animal Biotechnology (식품·동물생명공학부)Theses (Master's Degree_식품·동물생명공학부)
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