Details
| Original language | English |
|---|---|
| Pages (from-to) | 4360-4365 |
| Number of pages | 6 |
| Journal | Organic Letters |
| Volume | 22 |
| Issue number | 11 |
| Publication status | Published - 20 May 2020 |
Abstract
New sesquiterpene backbones are accessible after biotransformation of presilphiperfolan-8β-ol synthase (BcBOT2), a fungal sesquiterpene synthase, with non-natural farnesyldiphosphates in which methyl groups are shifted by one position toward the diphosphate terminus. One of the macrocycles formed, a new germacrene A derivative, undergoes a Cope rearrangement to iso-β-elemene. Three of the new terpenoids show olfactoric properties that range from an intense peppery note to a citrus, ozone-like, and fruity scent.
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: Organic Letters, Vol. 22, No. 11, 20.05.2020, p. 4360-4365.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Methyl-shifted farnesyldiphosphate derivatives are substrates for sesquiterpene cyclases
AU - Harms, Vanessa
AU - Schröder, Benjamin
AU - Oberhauser, Clara
AU - Tran, Cong Duc
AU - Winkler, Sven
AU - Dräger, Gerald
AU - Kirschning, Andreas
PY - 2020/5/20
Y1 - 2020/5/20
N2 - New sesquiterpene backbones are accessible after biotransformation of presilphiperfolan-8β-ol synthase (BcBOT2), a fungal sesquiterpene synthase, with non-natural farnesyldiphosphates in which methyl groups are shifted by one position toward the diphosphate terminus. One of the macrocycles formed, a new germacrene A derivative, undergoes a Cope rearrangement to iso-β-elemene. Three of the new terpenoids show olfactoric properties that range from an intense peppery note to a citrus, ozone-like, and fruity scent.
AB - New sesquiterpene backbones are accessible after biotransformation of presilphiperfolan-8β-ol synthase (BcBOT2), a fungal sesquiterpene synthase, with non-natural farnesyldiphosphates in which methyl groups are shifted by one position toward the diphosphate terminus. One of the macrocycles formed, a new germacrene A derivative, undergoes a Cope rearrangement to iso-β-elemene. Three of the new terpenoids show olfactoric properties that range from an intense peppery note to a citrus, ozone-like, and fruity scent.
UR - http://www.scopus.com/inward/record.url?scp=85085761903&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.0c01345
DO - 10.1021/acs.orglett.0c01345
M3 - Article
C2 - 32432889
AN - SCOPUS:85085761903
VL - 22
SP - 4360
EP - 4365
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 11
ER -