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

96 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

Access to Document

10.1021/ja3081154

Cite this

@article{74693c190d96467db3f563daabd6c739,

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",

year = "2012",

month = nov,

day = "7",

doi = "10.1021/ja3081154",

language = "English",

volume = "134",

pages = "18181--18184",

number = "44",

}

TY - JOUR

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.

UR - https://www.scopus.com/pages/publications/84868568903

UR - https://www.scopus.com/pages/publications/84868568903#tab=citedBy

U2 - 10.1021/ja3081154

DO - 10.1021/ja3081154

M3 - Article

C2 - 23102024

AN - SCOPUS:84868568903

SN - 0002-7863

VL - 134

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

Abstract

Funding

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this