Biocatalytic Process for (−)‐Ambrox Production Using Squalene Hopene Cyclase

Eichhorn, Eric; Locher, Esther; Guillemer, Sabrina; Wahler, Denis; Fourage, Laurent; Schilling, Boris

doi:10.1002/adsc.201800132

Cited by 54 publications

(106 citation statements)

References 38 publications

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“…Another innovative approach to Ambrofix (296)involves a" sesquiterpene-plus-C 1 "a pproach utilizing squalenehopene-cyclase (SHC). [265,266] Ther equired substrate (E,E)homofarnesol (EEH, 303)i ss ynthesized by selective cyclopropanation of (E)-b-farnesene (301)t o302, [267] followed by (E)-selective cyclopropyl-carbinyl rearrangement of the resulting vinyl cyclopropane. [268] (E)-b-Farnesene (301)i si n turn manufactured from sugar by engineered yeast fermentation.…”

Section: Ambery Notesmentioning

confidence: 99%

What's Hot, What's Not: The Trends of the Past 20 Years in the Chemistry of Odorants

et al. 2020

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This review is the sequel to the 2000 report on the recent advances in the chemistry of odorants and it summarizes the developments in fragrance chemistry over the past 20 years. Following the olfactory spectrum set out in that report, trendsetting so‐called captive odorants (patent‐protected ingredients unavailable to the market) are presented according to the main odor families: “fruity”, “marine”, “green”, “floral”, “spicy”, “woody”, “amber”, and “musky”. The design of odorants, their chemical synthesis, and their use in modern perfumery are illustrated with prominent examples. Featured are new fruity odorants that provide signature in the top note, as well as precursor technology. In the green domain, focus is on leafy notes and green pear. New benzodioxepines and benzodioxoles have modernized the marine family and required a revision of the existing olfactophore models. The replacement of Lilial and Lyral kept the industry busy in the floral domain with a plethora of new “muguets”. There was continued activity in the domain of rose odorants, especially in the area of rose ketones. Biotechnology became significant, for example, with Clearwood and Ambrofix, and the principal odorants of vetiver oil in the woody family have been found. Fourth and fifth families of musk odorants were also discovered and populated. Thus, new avenues for further explorations into fragrance chemistry have been opened.

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Section: Ambery Notesmentioning

confidence: 99%

What's Hot, What's Not: The Trends of the Past 20 Years in the Chemistry of Odorants

et al. 2020

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“…This result indicated that to further improve the scale of the catalytic conversion system was feasible and expecting for producing more hopene with high purity. SHC can also be used to produce other terpenoids, such as epoxydammarane (Ideno et al, 2018) and ambrox (Eichhorn et al, 2018;List and Sun, 2018). These valuable terpenoids can also be produced at a scale-up level by using the soluble OUC-SaSHC found in this study.…”

Section: Shc Has the Potential For Large-scale Production Of Hopenementioning

confidence: 93%

A Novel Soluble Squalene-Hopene Cyclase and Its Application in Efficient Synthesis of Hopene

Liu

Zhang

Sun

et al. 2020

Front. Bioeng. Biotechnol.

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Hopene is an important precursor for synthesizing bioactive hopanoids with great commercial value. However, the chemical methods for synthesizing hopene are not efficient to date. Hopene is commonly obtained by extracting from plants or bacteria like other terpenoids, but the complicated extraction process is inefficient and unfriendly to the environment. Hopene can be biological synthesized by squalene-hopene cyclase (SHC) from squalene. However, hopene production by SHC remained at a low level until now. In this work, we found a novel SHC named OUC-SaSHC from Streptomyces albolongus ATCC 27414. An easy procedure for expression and purification of OUC-SaSHC was established. The conditions for OUC-SaSHC to convert squalene into hopene are optimized as in 100 mM sodium phosphate buffer (pH 7.0) containing 0.5% Tween 80, 20 mM squalene and 0.14 mg/mL OUC-SaSHC at 30 • C. In the scale-up reaction with the final volume of 100 mL, the yield of squalene could be up to 99% at 36 h, and 8.07 mg/mL hopene was produced. Our work showed a great potential of OUC-SaSHC as biocatalyst on scale-up production of hopene, hence improves the SHC-catalyzing enzyme synthesis of hopene from laboratory level to application level.

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“…Im Zentrum dieser neuen Herstellungsmethode steht eine Squalen-Hopen-Cyclase katalysierte Polyencyclisierung. [265,266] Das bençtigte Substrat (E,E)-Homofarnesol (EEH, 303)wird durch selektive Cyclopropanierung von (E)b-Farnesen (301)zu302 [267] hergestellt, gefolgt von einer (E)selektiven Cyclopropyl-Carbinyl-Umlagerung. [268] (E)-b-Farnesen (301)wird durch einen Hefe-Fermentationsprozess aus Zucker hergestellt.…”

Section: Aufsätzeunclassified

Heiße Luft oder cooler Duft? Die Trends der letzten 20 Jahre in der Riechstoffchemie

et al. 2020

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Dieser Aufsatz ist die Fortsetzung unseres Berichtes über die neuesten Trends der Riechstoffchemie aus dem Jahr 2000 und fasst die Entwicklungen der letzten 20 Jahren zusammen. Dem selben Duftspektrum folgend, werden besonders richtungsweisende Captives (patentgeschützte Riechstoffe, die nicht frei verkäuflich sind) vorgestellt, und die Einteilung in die Geruchsfamilien “fruchtig”, “grün”, “marin”, “blumig”, “würzig”, “holzig”, “Ambra” und “Moschus” wird auch in dieser Übersicht beibehalten. Das Design von Riechstoffen, ihre chemische Synthese und ihre Verwendung in der modernen Parfümerie werden anhand von prominenten Beispielen illustriert. Unter anderem werden neue fruchtige Riechstoffe vorgestellt, die vor allem der Kopfnote von Parfüms eine besondere Signatur verleihen, aber auch durch Anwendung von Präkursor‐Technologien in der Basisnote einen olfaktorischen Beitrag leisten können. Bei den Grünnoten liegt der Schwerpunkt auf grünen Blättern und Birnen. Neue Benzodioxepine und Benzodioxole haben die marine Familie modernisiert und machten eine Überarbeitung der Olfaktophor‐Modelle notwendig. Bedeutende regulatorische Einschränkungen des Gebrauchs von Lilial und Lyral bereicherten die Parfümindustrie im floralen Bereich mit einer großen Fülle von neuen Maiglöckchen‐Riechstoffen. Darüber hinaus wurde intensiv nach neuen Rosen‐Riechstoffen geforscht, wobei ein besonderes Augenmerk auf Rosenketonen lag. Die Biotechnologie gewann signifikant an Bedeutung, wie mit Clearwood und Ambrofix belegt wird. In der holzigen Duftfamilie wurde das riechende Prinzip des Vetiveröls aufgeklärt. Eine vierte und sogar fünfte Verbindungsklasse von Moschus‐Riechstoffen wurde entdeckt, von denen einige Derivate besondere wirtschaftliche Bedeutung erlangten. All diese Aktivitäten eröffneten neue, zukunftsweisende Perspektiven und Forschungsrichtungen in der Chemie der Riechstoffe.

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Biocatalytic Process for (−)‐Ambrox Production Using Squalene Hopene Cyclase

Cited by 54 publications

References 38 publications

What's Hot, What's Not: The Trends of the Past 20 Years in the Chemistry of Odorants

What's Hot, What's Not: The Trends of the Past 20 Years in the Chemistry of Odorants

A Novel Soluble Squalene-Hopene Cyclase and Its Application in Efficient Synthesis of Hopene

Heiße Luft oder cooler Duft? Die Trends der letzten 20 Jahre in der Riechstoffchemie

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