Baeyer-villiger C-C bond cleavage reaction in gilvocarcin and jadomycin biosynthesis

Nidhi Tibrewal; Pallab Pahari; Guojun Wang; Madan K. Kharel; Caleb Morris; Theresa Downey; Yanpeng Hou; Tim S. Bugni; Jürgen Rohr

doi:10.1021/ja3081154

Baeyer-villiger C-C bond cleavage reaction in gilvocarcin and jadomycin biosynthesis

Nidhi Tibrewal, Pallab Pahari, Guojun Wang, Madan K. Kharel, Caleb Morris, Theresa Downey, Yanpeng Hou, Tim S. Bugni, Jürgen Rohr

Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

87 Scopus citations

Abstract

GilOII has been unambiguously identified as the key enzyme performing the crucial C-C bond cleavage reaction responsible for the unique rearrangement of a benz[a]anthracene skeleton to the benzo[d]naphthopyranone backbone typical of the gilvocarcin-type natural anticancer antibiotics. Further investigations of this enzyme led to the isolation of a hydroxyoxepinone intermediate, leading to important conclusions regarding the cleavage mechanism.

Original language	English
Pages (from-to)	18181-18184
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	134
Issue number	44
DOIs	https://doi.org/10.1021/ja3081154
State	Published - Nov 7 2012

Funding

Funders	Funder number
National Center for Research Resources	S10RR008438

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja3081154

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title = "Baeyer-villiger C-C bond cleavage reaction in gilvocarcin and jadomycin biosynthesis",

abstract = "GilOII has been unambiguously identified as the key enzyme performing the crucial C-C bond cleavage reaction responsible for the unique rearrangement of a benz[a]anthracene skeleton to the benzo[d]naphthopyranone backbone typical of the gilvocarcin-type natural anticancer antibiotics. Further investigations of this enzyme led to the isolation of a hydroxyoxepinone intermediate, leading to important conclusions regarding the cleavage mechanism.",

author = "Nidhi Tibrewal and Pallab Pahari and Guojun Wang and Kharel, {Madan K.} and Caleb Morris and Theresa Downey and Yanpeng Hou and Bugni, {Tim S.} and J{\"u}rgen Rohr",

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doi = "10.1021/ja3081154",

language = "English",

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T1 - Baeyer-villiger C-C bond cleavage reaction in gilvocarcin and jadomycin biosynthesis

AU - Tibrewal, Nidhi

AU - Pahari, Pallab

AU - Wang, Guojun

AU - Kharel, Madan K.

AU - Morris, Caleb

AU - Downey, Theresa

AU - Hou, Yanpeng

AU - Bugni, Tim S.

AU - Rohr, Jürgen

PY - 2012/11/7

Y1 - 2012/11/7

N2 - GilOII has been unambiguously identified as the key enzyme performing the crucial C-C bond cleavage reaction responsible for the unique rearrangement of a benz[a]anthracene skeleton to the benzo[d]naphthopyranone backbone typical of the gilvocarcin-type natural anticancer antibiotics. Further investigations of this enzyme led to the isolation of a hydroxyoxepinone intermediate, leading to important conclusions regarding the cleavage mechanism.

AB - GilOII has been unambiguously identified as the key enzyme performing the crucial C-C bond cleavage reaction responsible for the unique rearrangement of a benz[a]anthracene skeleton to the benzo[d]naphthopyranone backbone typical of the gilvocarcin-type natural anticancer antibiotics. Further investigations of this enzyme led to the isolation of a hydroxyoxepinone intermediate, leading to important conclusions regarding the cleavage mechanism.

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U2 - 10.1021/ja3081154

DO - 10.1021/ja3081154

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SP - 18181

EP - 18184

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 44

ER -

Baeyer-villiger C-C bond cleavage reaction in gilvocarcin and jadomycin biosynthesis

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