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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.

SUBMITTER: Tibrewal N 

PROVIDER: S-EPMC3498853 | biostudies-literature | 2012 Nov

REPOSITORIES: biostudies-literature

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Baeyer-Villiger C-C bond cleavage reaction in gilvocarcin and jadomycin biosynthesis.

Tibrewal Nidhi N   Pahari Pallab P   Wang Guojun G   Kharel Madan K MK   Morris Caleb C   Downey Theresa T   Hou Yanpeng Y   Bugni Tim S TS   Rohr Jürgen J  

Journal of the American Chemical Society 20121029 44

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. ...[more]