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Location of flavone B-ring controls regioselectivity and stereoselectivity of naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816-4.
Appl Microbiol Biotechnol. 2010 May; 86(5):1451-62.AM

Abstract

Naphthalene dioxygenase (NDO) from Pseudomonas sp. strain NCIB 9816-4 incorporated dioxygen at the C7 and C8 positions on the A-rings of flavone and isoflavone with different stereoselectivity, resulting in the formation of (7S,8S)-dihydroxy-2-phenyl-7,8-dihydro-4H-chromen-4-one (flavone-cis-(7S,8S)-dihydrodiol) and (7R,8R)-dihydroxy-3-phenyl-7,8-dihydro-4H-chromen-4-one (isoflavone-cis-(7R,8R)-dihydrodiol), respectively. In addition, NDO was shown to incorporate dioxygen at the C5 and C6 positions on the A-ring and the C2' and C3' positions on the B-ring of isoflavone, resulting in the production of (5S,6R)-dihydroxy-3-phenyl-5,6-dihydro-4H-chromen-4-one (isoflavone-cis-(5S,6R)-dihydrodiol) and 3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]-4H-chromen-4-one (isoflavone-cis-(2'R,3'S)-dihydrodiol), respectively. The metabolites were identified by LC/MS, (1)H, and (13)C NMR analyses and TD-SCF calculations combined with CD spectroscopy. In the case of flavone biotransformation, formation of flavone-(7S,8S)-dihydrodiol is likely to be the result of hydrogen bond interactions between the substrate and the active site of the dioxygenase. On the contrary, regioselective dioxygenation of isoflavone was found not to occur, and this may be due to the fact that the same hydrogen bonds that occur in the case of the flavone reaction cannot be established due to steric hindrance caused by the position of the B-ring. It is therefore proposed that the regioselectivity and stereoselectivity of NDO from strain NCIB 9816-4 are controlled by the position of the phenyl ring on flavone molecules.

Authors+Show Affiliations

Department of Environmental Science and Engineering, Gwangju Institute of Science and Technology, Gwangju, 500-712, South Korea.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

20091026

Citation

Seo, Jiyoung, et al. "Location of Flavone B-ring Controls Regioselectivity and Stereoselectivity of Naphthalene Dioxygenase From Pseudomonas Sp. Strain NCIB 9816-4." Applied Microbiology and Biotechnology, vol. 86, no. 5, 2010, pp. 1451-62.
Seo J, Kang SI, Ryu JY, et al. Location of flavone B-ring controls regioselectivity and stereoselectivity of naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816-4. Appl Microbiol Biotechnol. 2010;86(5):1451-62.
Seo, J., Kang, S. I., Ryu, J. Y., Lee, Y. J., Park, K. D., Kim, M., Won, D., Park, H. Y., Ahn, J. H., Chong, Y., Kanaly, R. A., Han, J., & Hur, H. G. (2010). Location of flavone B-ring controls regioselectivity and stereoselectivity of naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816-4. Applied Microbiology and Biotechnology, 86(5), 1451-62. https://doi.org/10.1007/s00253-009-2389-6
Seo J, et al. Location of Flavone B-ring Controls Regioselectivity and Stereoselectivity of Naphthalene Dioxygenase From Pseudomonas Sp. Strain NCIB 9816-4. Appl Microbiol Biotechnol. 2010;86(5):1451-62. PubMed PMID: 20091026.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Location of flavone B-ring controls regioselectivity and stereoselectivity of naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816-4. AU - Seo,Jiyoung, AU - Kang,Su-Il, AU - Ryu,Ji-Young, AU - Lee,Young-Ju, AU - Park,Ki Deok, AU - Kim,Mihyang, AU - Won,Dongho, AU - Park,Hye-Yeon, AU - Ahn,Joong-Hoon, AU - Chong,Youhoon, AU - Kanaly,Robert A, AU - Han,Jaehong, AU - Hur,Hor-Gil, Y1 - 2009/12/20/ PY - 2009/10/28/received PY - 2009/11/27/accepted PY - 2009/11/24/revised PY - 2010/1/22/entrez PY - 2010/1/22/pubmed PY - 2010/7/30/medline SP - 1451 EP - 62 JF - Applied microbiology and biotechnology JO - Appl. Microbiol. Biotechnol. VL - 86 IS - 5 N2 - Naphthalene dioxygenase (NDO) from Pseudomonas sp. strain NCIB 9816-4 incorporated dioxygen at the C7 and C8 positions on the A-rings of flavone and isoflavone with different stereoselectivity, resulting in the formation of (7S,8S)-dihydroxy-2-phenyl-7,8-dihydro-4H-chromen-4-one (flavone-cis-(7S,8S)-dihydrodiol) and (7R,8R)-dihydroxy-3-phenyl-7,8-dihydro-4H-chromen-4-one (isoflavone-cis-(7R,8R)-dihydrodiol), respectively. In addition, NDO was shown to incorporate dioxygen at the C5 and C6 positions on the A-ring and the C2' and C3' positions on the B-ring of isoflavone, resulting in the production of (5S,6R)-dihydroxy-3-phenyl-5,6-dihydro-4H-chromen-4-one (isoflavone-cis-(5S,6R)-dihydrodiol) and 3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]-4H-chromen-4-one (isoflavone-cis-(2'R,3'S)-dihydrodiol), respectively. The metabolites were identified by LC/MS, (1)H, and (13)C NMR analyses and TD-SCF calculations combined with CD spectroscopy. In the case of flavone biotransformation, formation of flavone-(7S,8S)-dihydrodiol is likely to be the result of hydrogen bond interactions between the substrate and the active site of the dioxygenase. On the contrary, regioselective dioxygenation of isoflavone was found not to occur, and this may be due to the fact that the same hydrogen bonds that occur in the case of the flavone reaction cannot be established due to steric hindrance caused by the position of the B-ring. It is therefore proposed that the regioselectivity and stereoselectivity of NDO from strain NCIB 9816-4 are controlled by the position of the phenyl ring on flavone molecules. SN - 1432-0614 UR - https://www.unboundmedicine.com/medline/citation/20091026/Location_of_flavone_B_ring_controls_regioselectivity_and_stereoselectivity_of_naphthalene_dioxygenase_from_Pseudomonas_sp__strain_NCIB_9816_4_ L2 - https://dx.doi.org/10.1007/s00253-009-2389-6 DB - PRIME DP - Unbound Medicine ER -