Methyl-shifted farnesyldiphosphate derivatives are substrates for sesquiterpene cyclases

Vanessa Harms; Benjamin Schröder; Clara Oberhauser; Cong Duc Tran; Sven Winkler; Gerald Dräger; Andreas Kirschning

doi:10.1021/acs.orglett.0c01345

Methyl-shifted farnesyldiphosphate derivatives are substrates for sesquiterpene cyclases

Vanessa Harms
, Benjamin Schröder
, Clara Oberhauser
, Cong Duc Tran
, Sven Winkler
, Gerald Dräger
, Andreas Kirschning^*

^*Corresponding author for this work

Symrise AG

Research output: Contribution to journal › Article › Research › peer review

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.

Original language	English
Pages (from-to)	4360-4365
Number of pages	6
Journal	Organic Letters
Volume	22
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.0c01345
Publication status	Published - 20 May 2020

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.0c01345

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title = "Methyl-shifted farnesyldiphosphate derivatives are substrates for sesquiterpene cyclases",

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. ",

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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 - https://www.scopus.com/pages/publications/85085761903

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DO - 10.1021/acs.orglett.0c01345

M3 - Article

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AN - SCOPUS:85085761903

SN - 1523-7060

VL - 22

SP - 4360

EP - 4365

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

Methyl-shifted farnesyldiphosphate derivatives are substrates for sesquiterpene cyclases

Abstract

ASJC Scopus subject areas

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