Details
| Original language | English |
|---|---|
| Pages (from-to) | 7833-7839 |
| Number of pages | 7 |
| Journal | Organic & Biomolecular Chemistry |
| Volume | 20 |
| Issue number | 39 |
| Publication status | Published - 12 Oct 2022 |
Abstract
New homo-sesquiterpenes are accessible after conversion of presilphiperfolan-8β-ol synthase (BcBOT2) with cyclopropylmethyl analogs of farnesyl diphosphate, and this biotransformation is dependent on subtle structural refinements. Two of the three cyclisation products are homo variants of germacrene D and germacrene D-4-ol while the third product reported contains a new bicyclic backbone for which no analogue in nature has been described so far. The findings on diphosphate activation are discussed and rationalised by relaxed force constants and dissociation energies computed at the DFT level of theory.
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 & Biomolecular Chemistry, Vol. 20, No. 39, 12.10.2022, p. 7833-7839.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Cyclopropylmethyldiphosphates are substrates for sesquiterpene synthases
T2 - experimental and theoretical results
AU - Tran, Cong Duc
AU - Dräger, Gerald
AU - Struwe, Henry Frederik
AU - Siedenberg, Lukas
AU - Vasisth, Somi
AU - Grunenberg, Jörg
AU - Kirschning, Andreas
N1 - Funding Information: We thank Prof. Dr. Sascha Beutel (LUH) for support in protein production and Dr. Linn Müggenburg (LUH) for NMR support.
PY - 2022/10/12
Y1 - 2022/10/12
N2 - New homo-sesquiterpenes are accessible after conversion of presilphiperfolan-8β-ol synthase (BcBOT2) with cyclopropylmethyl analogs of farnesyl diphosphate, and this biotransformation is dependent on subtle structural refinements. Two of the three cyclisation products are homo variants of germacrene D and germacrene D-4-ol while the third product reported contains a new bicyclic backbone for which no analogue in nature has been described so far. The findings on diphosphate activation are discussed and rationalised by relaxed force constants and dissociation energies computed at the DFT level of theory.
AB - New homo-sesquiterpenes are accessible after conversion of presilphiperfolan-8β-ol synthase (BcBOT2) with cyclopropylmethyl analogs of farnesyl diphosphate, and this biotransformation is dependent on subtle structural refinements. Two of the three cyclisation products are homo variants of germacrene D and germacrene D-4-ol while the third product reported contains a new bicyclic backbone for which no analogue in nature has been described so far. The findings on diphosphate activation are discussed and rationalised by relaxed force constants and dissociation energies computed at the DFT level of theory.
UR - http://www.scopus.com/inward/record.url?scp=85139739624&partnerID=8YFLogxK
U2 - 10.1039/d2ob01279k
DO - 10.1039/d2ob01279k
M3 - Article
C2 - 36169604
AN - SCOPUS:85139739624
VL - 20
SP - 7833
EP - 7839
JO - Organic & Biomolecular Chemistry
JF - Organic & Biomolecular Chemistry
SN - 1477-0520
IS - 39
ER -