An enzymatic approach to the synthesis of optically pure (3R)- and (3S)-enantiomers of green tea flavor compound 3-hydroxy-3-methylnonane-2,4-dione

Bortolini, Olga; Giovannini, Pier Paolo; Maietti, Silvia; Massi, Alessandro; Pedrini, Paola; Sacchetti, Gianni; Venturi, Valentina

doi:10.1016/j.molcatb.2012.08.015

Cited by 8 publications

(6 citation statements)

References 36 publications

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“…The optically active products 97, some of which are known flavoring agents [111], always showed R configurations and ee values ranging from 67 to 91% [112]. This homocoupling of α-diketones has also been reported using continuous-flow conditions in a packed-bed reactor, in which the purified enzyme purified had been immobilized onto mesoporous silica [113].…”

Section: Biocatalytic Synthesis Of 13-diketonessupporting

confidence: 61%

Recent Developments in the Synthesis of β-Diketones

Gonzalo

Alcántara

2021

Pharmaceuticals

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Apart from being one of the most important intermediates in chemical synthesis, broadly used in the formation of C–C bonds among other processes, the β-dicarbonyl structure is present in a huge number of biologically and pharmaceutically active compounds. In fact, mainly derived from the well-known antioxidant capability associated with the corresponding enol tautomer, β-diketones are valuable compounds in the treatment of many pathological disorders, such as cardiovascular and liver diseases, hypertension, obesity, diabetes, neurological disorders, inflammation, skin diseases, fibrosis, or arthritis; therefore, the synthesis of these structures is an area of overwhelming interest for organic chemists. This paper is devoted to the advances achieved in the last ten years for the preparation of 1,3-diketones, using different chemical (Claisen, hydration of alkynones, decarboxylative coupling) or catalytic (biocatalysis, organocatalytic, metal-based catalysis) methodologies: Additionally, the preparation of branched β-dicarbonyl compounds by means of α-functionalization of non-substituted 1,3-diketones are also discussed.

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Section: Biocatalytic Synthesis Of 13-diketonessupporting

confidence: 61%

Recent Developments in the Synthesis of β-Diketones

Gonzalo

Alcántara

2021

Pharmaceuticals

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“…Coupling a ThDP-dependent acetylacetoin synthase (AAS) from Bacillus licheniformis to the NADH-dependent acetylacetoin reductase (AAR) from the same organism allowed to access syn -α-alkyl-α,β-dihydroxyketones with high enantioselectivities (>95% ee; Scheme ) and good isolated yields (60–70%). , It is important to note that symmetrical diketones obtained from homocoupling were not reduced by the ( S )-stereospecific reductase (AAR) and could be separated from the final products by flash chromatography. The reaction sequence was also employed for the synthesis of the chiral green tea flavor compound 3-hydroxy-3-methylnonane-2,4-dione …”

Section: In Vitro Cascades Requiring For Each Step a Biocatalystmentioning

confidence: 99%

Artificial Biocatalytic Linear Cascades for Preparation of Organic Molecules

et al. 2017

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The review compiles artificial cascades involving enzymes with a focus on the last 10 years. A cascade is defined as the combination of at least two reaction steps in a single reaction vessel without isolation of the intermediates, whereby at least one step is catalyzed by an enzyme. Additionally, cascades performed in vivo and in vitro are discussed separately, whereby in vivo cascades are defined here as cascades relying on cofactor recycling by the metabolism or on a metabolite from the living organism. The review introduces a systematic classification of the cascades according to the number of enzymes in the linear sequence and differentiates between cascades involving exclusively enzymes and combinations of enzymes with non-natural catalysts or chemical steps. Since the number of examples involving two enzymes is predominant, the two enzyme cascades are further subdivided according to the number, order, and type of redox steps. Furthermore, this classification differentiates between cascades where all reaction steps are performed simultaneously, sequentially, or in flow.

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“…As a consequence, it was possible to deduce the ( R ) configuration of the α‐quaternary stereocenter (Scheme ). Thanks to the combined use of AAS and AAR from Bacillus licheniformis , both the enantiomers of 3‐hydroxy‐3‐methylnonane‐2,4‐dione, one of the main components of the volatile fraction responsible for the peculiar flavor of green tea infuses, have been synthesized (Scheme ) …”

Section: Acyloin‐type Reactionsmentioning

confidence: 99%

Building Up Quaternary Stereocenters Through Biocatalyzed Direct Insertion of Carbon Nucleophiles on Ketones

Gaggero

2019

Eur J Org Chem

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Quaternary stereocenters are privileged structural motifs, widely distributed in natural products and in pharmaceutically active compounds. Asymmetric methods for the efficient construction of these prominent frameworks are rapidly increasing. Biocatalysis represents an alternative to the existing methods of using hazardous metals and chemicals. Enzymes discussed in this mini-review involve thiamine-bisphosphate (ThDP)-dependent lyases, aldolases and hydroxynitrile lyases.[a] 7616 of CO 2 is transferred to the si face of an aldehyde acceptor to give an (R)-hydroxy ketone (Scheme 2). Scheme 2. Catalytic cycle of ThDP-dependent acyloin reaction.

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An enzymatic approach to the synthesis of optically pure (3R)- and (3S)-enantiomers of green tea flavor compound 3-hydroxy-3-methylnonane-2,4-dione

Cited by 8 publications

References 36 publications

Recent Developments in the Synthesis of β-Diketones

Recent Developments in the Synthesis of β-Diketones

Artificial Biocatalytic Linear Cascades for Preparation of Organic Molecules

Building Up Quaternary Stereocenters Through Biocatalyzed Direct Insertion of Carbon Nucleophiles on Ketones

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