Firmenich Sa

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University of Kentucky Research Foundation

Michel Schalk

Laurent Daviet

Fabienne Deguerry

Letizia Rocci

Daniel Solis Escalante

Anthony Clark

Jens Nielsen

Verena Siewers

Pauline Anziani

Christian Goerner

Qi Rong Wang

Joe Chappell

Jens Bredal Nielsen

Xiu-Feng He

Monica Bandera

Pan Li

Olivier Haefliger

Yang Huang

Shuiqin Wu

Yu-Hua Zhang

Xiufeng He

Christoph Knuf

Gionata Scalcinati

Yun Chen

Jérôme Maury

Mohammad Ali Asadollahi

Kasper Møller

Athony Clark

Vincent Harraca

Described herein is a biochemically produced sandalwood oil including at least 85% santalol and bergamotol and 1% or less cis-lanceol, where the oil has one or more of the following features: i) 5% or less alpha-santalal; ii) 5% or less farnesol; and iii) 0.5% or less spirosantalol. Also described herein are a perfuming composition including the sandalwood oil and a perfuming consumer product including the sandalwood oil. Also described herein are a method of using the biochemically produced sandalwood oil as an anti-microbial and anti-inflammatory agent, and an arthropod control composition including the sandalwood oil.

Biochemically produced sandalwood oil

Described herein are the nucleic acid and the amino acid sequences of a cytochrome P450 capable of oxidizing terpene molecules. Also described herein are methods of oxidizing terpene molecules including contacting the cytochrome P450 with the terpene molecule intended to be oxidized. In particular, the method may be carried out in vitro or in vivo to produce oxidized terpene molecules, which may be used in different technical fields such as for example perfumery and flavoring. Also described herein is an expression vector containing the nucleic acid. A non-human host organism or a cell transformed with the nucleic acid is also an object of the disclosure.

Cytochrome P450 monooxygenase catalyzed oxidation of sesquiterpenes

Described herein is a method of producing a drimane sesquiterpene such as albicanol, drimenol and/or derivatives thereof by contacting at least one polypeptide with farnesyl diphosphate (FPP) with a polypeptide including a Haloacid dehalogenase (HAD)-like hydrolase domain and having bifunctional terpene synthase activity. The method may be performed in vitro or in vivo. Also described herein are amino acid sequences of polypeptides useful in the methods and nucleic acids encoding the polypeptides described. The described method further provides host cells or organisms genetically modified to express the polypeptides and useful to produce a drimane sesquiterpene such as albicanol, drimenol and/or derivatives thereof.

Method for producing albicanol and/or drimenol

Described herein is a method of producing a drimane sesquiterpene such as albicanol, drimenol and/or derivatives thereof by contacting at least one polypeptide with farnesyl diphosphate (FPP) with a polypeptide comprising a Haloacid dehalogenase (HAD)-like hydrolase domain and having bifunctional terpene synthase activity. The method may be performed in vitro or in vivo. Also described herein are amino acid sequences of polypeptides useful in the methods and nucleic acids encoding the polypeptides described. The described method further provides host cells or organisms genetically modified to express the polypeptides and useful to produce a drimane sesquiterpene such as albicanol, drimenol and/or derivatives thereof.

Provided is a method of producing one or more sesquiterpene compounds comprising: contacting an acyclic FPP precursor with a polypeptide having terpene synthase activity, wherein the polypeptide comprises an amino acid sequence that has at least 55% sequence identity to SEQ ID NO: 1, to produce one or more terpenes selected from the group consisting of isovalencene, spirovetiva-1(10),7(11)-diene and valencene or derivatives thereof, or mixture of sesquiterpenes comprising one or more of isovalencene, spirovetiva-1(10),7(11)-diene and/or valencene; and optionally isolating the one or more terpenes or the mixture. Also described is a nucleic acid derived fromencoding a polypeptide having sesquiterpene synthase activity, a polypeptide that can be used to produce one or more sesquiterpenes or a mixture of sesquiterpenes comprising one or more of isovalencene, spirovetiva-1(10),7(11)-diene and/or valencene, and a non-human organism or cell comprising the nucleic acid or comprising an expression vector comprising the nucleic acid.

Methods of producing sesquiterpene compounds

Provided herein are biocatalytic methods of producing terpene compounds by applying a novel type of phosphatase enzyme. The method allows the fully biochemical synthesis of terpene compounds, like for example copalol and labdendiol, and derivatives thereof, which serve as valuable intermediates for the production of perfumery ingredients, such as, for example, ambrox. Also provided are novel fully biochemical multistep processes for the production of such compounds as well as novel phosphatase enzymes and mutants and variants derived therefrom.

Method for biocatalytic production of terpene compounds

This invention relates generally to methods and compositions for producing a sesquiterpene alcohol comprising contacting a sesquiterpene with a P450 polypeptide with monooxygenase activity.

Method for producing fragrant alcohols

Described herein are methods of producing (+)-manool, the methods including: contacting geranylgeranyl diphosphate with a copalyl diphosphate (CPP) synthase to form a (9S, 10S)-copalyl diphosphate and contacting the CPP with a sclareol synthase enzyme to form (+)-manool and derivatives thereof. Also described herein are nucleic acids encoding CPP synthases and sclareol synthases for use in the methods. Further described herein are expression vectors and non-human host organisms and cells including nucleic acids encoding a CPP synthase and a sclareol synthase as described herein.

Production of manool

The present invention relates to a method of producing drimenol and/or drimenol derivatives by contacting at least one polypeptide with farnesyl diphosphate. The method may be performed in vitro or in vivo. The present invention also provides amino acid sequences of polypeptides useful in the method of the invention and nucleic acid encoding the polypeptides of the invention. The method further provides host cells or organisms genetically modified to express the polypeptides of the invention and useful to produce drimenol and/or drimenol derivatives.

Drimenol synthases II

Provided herein are methods of producing (+)-manool comprising: contacting geranylgeranyl diphosphate with an copalyl diphosphate (CPP) synthase to form a (9S, 10S)-copalyl diphosphate wherein the CPP synthase comprises an amino acid sequence having at least 90%, 95%, 98%, 99% and 100% sequence identity to a polypeptide selected from the group consisting of SEQ ID NO: 1 and SEQ ID NO:2; and contacting the CPP with a sclareol synthase enzyme to form (+)-manool.

Provided herein is an isolated polypeptide from'Beverleyensis' orcomprising a (+)-cedrol or a (&#x2212;)-thujopsene synthase. Further provided herein is an isolated nucleic acid molecule from'Beverleyensis' orencoding a (+)-cedrol or (&#x2212;)-thujopsene synthase. Further provided herein are methods of producing (+)-cedrol or (&#x2212;)-thujopsene.

Production of fragrant compounds

The present invention provides a method of producing &#x3b2;-santalene, said method comprising contacting at least one polypeptide with farnesyl pyrophosphate (FPP). In particular, said method may be carried out in vitro or in vivo to produce &#x3b2;-santalene, a very useful compound in the fields of perfumery and flavoring. The present invention also provides the amino acid sequence of a polypeptide useful in the method of the invention. A nucleic acid encoding the polypeptide of the invention and an expression vector containing said nucleic acid are also part of the present invention. A non-human host organism or a cell transformed to be used in the method of producing &#x3b2;-santalene is also an object of the present invention.

Method for producing beta-santalene

The present invention provides the nucleic acid and the amino acid sequences of a cytochrome P450 capable of oxidizing terpene molecules. It also provides a method of oxidizing terpene molecules comprising contacting the cytochrome P450 of the invention with the terpene molecule intended to be oxidized. In particular, said method may be carried out in vitro or in vivo to produce oxidized terpene molecules, which may be used in different technical fields such as for example perfumery and flavoring. The present invention also provides an expression vector containing the nucleic acid. A non-human host organism or a cell transformed with the nucleic acid is also an object of the invention.

Cytochrome P450 and use thereof for the enzymatic oxidation of terpenes

The present invention provides a method of producing &#x3b1;-santalene by contacting at least one polypeptide with farnesyl phyrophosphate (fpp). In particular, the method may be carried out in vitro or in vivo to produce &#x3b1;-santalene, a very useful compound in the fields of perfumery and flavoring. The present invention also provides the amino acid sequence of a polypeptide useful in the method of the invention. A nucleic acid encoding the polypeptide of the invention and an expression vector containing the nucleic acid represent part of the present invention. A non-human host organism and a cell transformed to be used in the method of producing &#x3b1; santalene are also part of the present invention.

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Geneva, Switzerland

Michel Schalk