TY - JOUR
T1 - A Non-Enzymatic Pathway with Superoxide in Intracellular Terpenoid Synthesis
AU - Ueda, Daijiro
AU - Matsugane, Saori
AU - Okamoto, Wataru
AU - Hashimoto, Masayuki
AU - Sato, Tsutomu
N1 - Funding Information:
This work was supported in part by JSPS KAKENHI (Grant no. 25108709, 16K14911 and 18H02145 to T.S., and 15J03090 to D.U.) and the Ministry of Science and Technology of Taiwan, ROC [grant no. 102-2320-B-006-004] (M.H.). We are grateful to Dr. Masahiro Fujihashi from Kyoto University and Dr. Tetsuro Shinada from Osaka City University for helpful discussions.
Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2018/8/6
Y1 - 2018/8/6
N2 - Non-C5-units terpenoids (norisoprenoids) with an acetonyl group are widely distributed in nature. However, studies on the biosynthesis of norisoprenoids are scarce. Now, the C33 norisoprenoid, (all-E)-farnesylfarnesylacetone, was identified from Bacillus spp. and it was elucidated for the first time that superoxide mediates the cleavage of menaquinones (vitamin K) to form norisoprenoids in saponification treatment. From in vivo experiments using gene-disrupted Bacillus subtilis strains targeted for enzymes responsible for menaquinone biosynthesis and for superoxide dismutase, it was suggested that the non-enzymatic cleavage (autoxidation) of menaquinone with superoxide resulted in norisoprenoid synthesis in Bacillus cells. Furthermore, the bioactive norisoprenoids, farnesylacetone and phytone, were produced in Bacillus cells by this novel synthesis system.
AB - Non-C5-units terpenoids (norisoprenoids) with an acetonyl group are widely distributed in nature. However, studies on the biosynthesis of norisoprenoids are scarce. Now, the C33 norisoprenoid, (all-E)-farnesylfarnesylacetone, was identified from Bacillus spp. and it was elucidated for the first time that superoxide mediates the cleavage of menaquinones (vitamin K) to form norisoprenoids in saponification treatment. From in vivo experiments using gene-disrupted Bacillus subtilis strains targeted for enzymes responsible for menaquinone biosynthesis and for superoxide dismutase, it was suggested that the non-enzymatic cleavage (autoxidation) of menaquinone with superoxide resulted in norisoprenoid synthesis in Bacillus cells. Furthermore, the bioactive norisoprenoids, farnesylacetone and phytone, were produced in Bacillus cells by this novel synthesis system.
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U2 - 10.1002/anie.201805383
DO - 10.1002/anie.201805383
M3 - Article
C2 - 29927025
AN - SCOPUS:85050500495
SN - 1433-7851
VL - 57
SP - 10347
EP - 10351
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 32
ER -