Production of optically pure (–)-borneol by Pseudomonas monteilii TCU-CK1 and characterization of borneol dehydrogenase involved

Khine, Aye Aye; Yang, Ming-Yeh; Hu, Anren; Lin, Guang-Huey; Toh, Yee-Huan; Chen, Hao‐Ping

doi:10.1016/j.enzmictec.2020.109586

Cited by 13 publications

(7 citation statements)

References 20 publications

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“…In contrast to all other described BDH enzymes so far (Polichuk et al 2010;Sarker et al 2012;Tian et al 2015;Tsang et al 2016;Drienovská et al 2020;Khine et al 2020), BDH from Pseudomonas sp. ATC17453 is able to catalyze the reduction of camphor to borneol with a maximal conversion rate at 30°C and a pH optimum at 4.5 (Fig.…”

Section: Reduction Of Camphormentioning

confidence: 66%

“…The activity of BDH from Pseudomonas sp. ATCC17453 is much higher than the known BDH from plant (Croteau et al 1978;Dehal and Croteau 1987;Polichuk et al 2010;Tian et al 2015;Fu et al 2016;Drienovská et al 2020) (Khine et al 2020). Interestingly, this enzyme is also the first BDH enzyme, which prefers (+)-borneol as substrate.…”

Section: Discussionmentioning

confidence: 88%

“…ATCC17453 shows no enantioselectivity, it is the first BDH enzyme capable of catalyzing the reverse reaction from camphor to borneol. None of the other studies regarding borneol dehydrogenase has analyzed the reverse reaction (Croteau et al 1978;Dehal and Croteau 1987;Polichuk et al 2010;Tian et al 2015;Fu et al 2016;Drienovská et al 2020;Khine et al 2020) nor could detect any reductive activity of the enzyme so far (Sarker et al 2012). A tropinone reductaselike short-chain reductase was reported, able to convert pure (+)-camphor and (−)-borneol with a k cat of 0.06 and 0.09, respectively (Reinhardt et al 2014).…”

Section: Discussionmentioning

confidence: 99%

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Engineering of a borneol dehydrogenase from P. putida for the enzymatic resolution of camphor

Hofer

Diener

Begander

et al. 2021

Appl Microbiol Biotechnol

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Several thousand different terpenoid structures are known so far, and many of them are interesting for applications as pharmaceuticals, flavors, fragrances, biofuels, insecticides, or fine chemical intermediates. One prominent example is camphor, which has been utilized since ancient times in medical applications. Especially (−)-camphor is gaining more and more interest for pharmaceutical applications. Hence, a commercial reliable source is needed. The natural sources for (−)-camphor are limited, and the oxidation of precious (−)-borneol would be too costly. Hence, synthesis of (−)-camphor from renewable alpha-pinene would be an inexpensive alternative. As the currently used route for the conversion of alpha-pinene to camphor produces a mixture of both enantiomers, preferably catalytic methods for the separation of this racemate are demanded to yield enantiopure camphor. Enzymatic kinetic resolution is a sustainable way to solve this challenge but requires suitable enzymes. In this study, the first borneol dehydrogenase from Pseudomonas sp. ATCC 17453, capable of catalyzing the stereoselective reduction of camphor, was examined. By using a targeted enzyme engineering approach, enantioselective enzyme variants were created with E-values > 100. The best variant was used for the enzymatic kinetic resolution of camphor racemate, yielding 79% of (−)-camphor with an ee of > 99%. Key points • Characterization of a novel borneol dehydrogenase (BDH) from P. putida. • Development of enantioselective BDH variants for the reduction of camphor. • Enzymatic kinetic resolution of camphor with borneol dehydrogenase. Graphical abstract

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Section: Reduction Of Camphormentioning

confidence: 66%

Section: Discussionmentioning

confidence: 88%

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Engineering of a borneol dehydrogenase from P. putida for the enzymatic resolution of camphor

Hofer

Diener

Begander

et al. 2021

Appl Microbiol Biotechnol

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“…BA is synthesized by acetylation of borneol, which has three optical isomers, including levorotatory, dextrorotatory, and racemate (Drienovská et al, 2020;Chánique et al, 2021). In contrast, chemically synthesized borneol contains four different stereoisomers, (+)-borneol, (−)-borneol, (+)isoborneol, and (−)-isoborneol (Khine et al, 2020). However, the AAT responsible for the synthesis of BA and other monoterpene acetates in W. villosa has not yet been characterized; furthermore, the gene encoding borneol acetyltransferase (BAT) catalyzing different types of borneol to synthesize BA has not yet been reported to date.…”

Section: Introductionmentioning

confidence: 99%

Genome-Wide Identification of BAHD Superfamily and Functional Characterization of Bornyl Acetyltransferases Involved in the Bornyl Acetate Biosynthesis in Wurfbainia villosa

et al. 2022

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Bornyl acetate (BA) is known as a natural aromatic monoterpene ester with a wide range of pharmacological and biological activities. Borneol acetyltransferase (BAT), catalyzing borneol and acetyl-CoA to synthesize BA, is alcohol acetyltransferase, which belongs to the BAHD super acyltransferase family, however, BAT, responsible for the biosynthesis of BA, has not yet been characterized. The seeds of Wurfbainia villosa (homotypic synonym: Amomum villosum) are rich in BA. Here we identified 64 members of the BAHD gene family from the genome of W. villosa using both PF02458 (transferase) and PF07247 (AATase) as Hidden Markov Model (HMM) to screen the BAHD genes. A total of sixty-four WvBAHDs are distributed on 14 chromosomes and nine unanchored contigs, clustering into six clades; three WvBAHDs with PF07247 have formed a separated and novel clade: clade VI. Twelve candidate genes belonging to clade I-a, I-b, and VI were selected to clone and characterize in vitro, among which eight genes have been identified to encode BATs acetylating at least one type of borneol to synthesize BA. All eight WvBATs can utilize (−)-borneol as substrates, but only five WvBATs can catalyze (+)-borneol, which is the endogenous borneol substrate in the seeds of W. villosa; WvBAT3 and WvBAT4 present the better catalytic efficiency on (+)-borneol than the others. The temporal and spatial expression patterns of WvBATs indicate that WvBAT3 and WvBAT4 are seed-specific expression genes, and their expression levels are correlated with the accumulation of BA, suggesting WvBAT3 and WvBAT4 might be the two key BATs for BA synthesis in the seeds of W. villosa. This is the first report on BAT responsible for the last biosynthetic step of BA, which will contribute to further studies on BA biosynthesis and metabolism engineering of BA in other plants or heterologous hosts.

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“…[8][9][10] Borneol, a bicyclic chiral monoterpene, is found in the essential oils of medicinal plants and is commonly used in traditional Chinese medicine for analgesia and anesthesia. [11][12] Borneol derivatives have been intensively studied in the field of medicinal, food and material chemistry. [13][14] Although research on borneol has led to a significantly enhanced understanding of its properties during the past few decades, the rational design of borneol derivatives to efficiently enhance their properties is still a challenge.…”

Section: Introductionmentioning

confidence: 99%

Low Symmetric meso-Borneol and meso-Carbazole Substituted H3Corroles: Synthesis, Characterization and Their Anticancer Behaviors

Rongping¹,

Zhouqun²,

Lin³

et al. 2021

MHC

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Two A 2 B type free base corroles with meso-borneol substituents at the B position have been synthesized and characterized. A detailed analysis of the optical and redox properties was carried out, and a comparison was made with theoretical calculations to identify the key trends in the structure-property relationships. The meso-borneol substituent couples strongly with the porphyrin core leading to significant CD signals in the B band region. Enhanced anti-cancer properties are observed in vitro relative to the introduction of (-)-borneol units.

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Production of optically pure (–)-borneol by Pseudomonas monteilii TCU-CK1 and characterization of borneol dehydrogenase involved

Cited by 13 publications

References 20 publications

Engineering of a borneol dehydrogenase from P. putida for the enzymatic resolution of camphor

Engineering of a borneol dehydrogenase from P. putida for the enzymatic resolution of camphor

Genome-Wide Identification of BAHD Superfamily and Functional Characterization of Bornyl Acetyltransferases Involved in the Bornyl Acetate Biosynthesis in Wurfbainia villosa

Low Symmetric meso-Borneol and meso-Carbazole Substituted H3Corroles: Synthesis, Characterization and Their Anticancer Behaviors

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