Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 10347-10351 |
| Number of pages | 5 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 57 |
| Issue number | 32 |
| DOIs | |
| Publication status | Published - 2018 Aug 6 |
Fingerprint
All Science Journal Classification (ASJC) codes
- Catalysis
- Chemistry(all)
Cite this
}
A Non-Enzymatic Pathway with Superoxide in Intracellular Terpenoid Synthesis. / Ueda, Daijiro; Matsugane, Saori; Okamoto, Wataru; Hashimoto, Masayuki; Sato, Tsutomu.
In: Angewandte Chemie - International Edition, Vol. 57, No. 32, 06.08.2018, p. 10347-10351.Research output: Contribution to journal › Article
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
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.
UR - http://www.scopus.com/inward/record.url?scp=85050500495&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85050500495&partnerID=8YFLogxK
U2 - 10.1002/anie.201805383
DO - 10.1002/anie.201805383
M3 - Article
VL - 57
SP - 10347
EP - 10351
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 32
ER -