Systematic Characterization of the Metabolism of Acetoin and Its Derivative Ligustrazine in <i>Bacillus subtilis</i> under Micro-Oxygen Conditions

Xu, Youqiang; Jiang, Yuefeng; Li, Xiuting; Sun, Baoguo; Chen, Teng; Yang, Ran; Xiong, Ke; Fan, Guangsen; Wang, Wenhua

doi:10.1021/acs.jafc.8b00113

Cited by 38 publications

(35 citation statements)

References 30 publications

(72 reference statements)

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“…The pyrazines might come from Strecker reaction, [17] and some strains like Bacillus were found capable to produce it. [21,22] Furan(one)s showed significant influence on the aroma of some similar fermented products, such as soy sauce and soybean paste. [4,5] They might result from lots of pathways including biosynthesis, [13] Maillard reaction, [23] and fatty acid oxidation.…”

Section: Html)mentioning

confidence: 99%

Flavor volatiles evolution of Chinese horse bean-chili-paste during ripening, accessed by GC×GC-TOF/MS and GC-MS-olfactometry

Tan

et al. 2020

International Journal of Food Properties

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The evolution of volatile compounds during the ripening of Chinese horse bean-chili-paste (CHCP) was investigated in this study. GC×GC-TOF/MS allowed an identification of 748 volatiles in three CHCP samples, respectively, ripened for 3 months (M3), 12 months (M12) and 24 months (M24), and it showed that a longer ripening resulted in a richer diversity of the volatiles. In addition, M3 contained more aldehydes and organic acids in content and M12 had more alcohols, ketones, and esters, while M24 was abundant in heterocyclics. A total of 69 among the 748 volatiles were discriminated as the key flavor compounds of CHCP by method of Fisher ratio together with odor activity value and flavor dilution, including 12 alcohols, 9 aldehydes, 4 ketones, 5 organic acids, 16 esters, 4 phenols, 6 sulfur-containing compounds, and 13 heterocyclics. Further, principal component analysis suggested that some key aldehydes contributed the flavor of M3, while some key alcohols, esters and heterocyclics existed in M12, and some key phenols and heterocyclics were in M24. Varying of the key flavor volatiles during CHCP ripening gave it different fragrance configurations. Results presented details for the volatile profiles of CHCP during the natural ripening period, beneficial to shorten fermentation time by functional microorganisms, and could enrich the desire flavors.

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Section: Html)mentioning

confidence: 99%

Flavor volatiles evolution of Chinese horse bean-chili-paste during ripening, accessed by GC×GC-TOF/MS and GC-MS-olfactometry

Tan

et al. 2020

International Journal of Food Properties

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“…It is worth noting that two molecules of acetoin (C 4 H 8 O 2 ) can be chemically converted to one molecule of 2,3,5,6-tetramethylpyrazine (TMP, C 8 H 12 N 2 , also called ligustrazine) in the presence of inorganic ammonium salts such as (NH 4 ) 2 SO 4 or diammonium phosphate [6,30]. As shown in Fig.…”

Section: Effect Of Enhancing the Acetoin Synthesis Pathway On Acetoinmentioning

confidence: 99%

“…At present, the commercial production of acetoin is mostly based on chemical methods with many disadvantages, such as high cost, high pollution, and low yield [5]. Moreover, the use of chemosynthetic, non-natural acetoin in food and cosmetics is restricted due to safety concerns [6,7].…”

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confidence: 99%

Engineering central pathways for industrial-level (3R)-acetoin biosynthesis in Corynebacterium glutamicum

Mao

Kou

et al. 2020

Preprint

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Background: Acetoin, especially the optically pure (3S)- or (3R)-enantiomer, is a high-value-added bio-based platform chemical and important potential pharmaceutical intermediate. Over the past decades, intense efforts have been devoted to the production of acetoin through green biotechniques. However, efficient and economical methods for the production of optically pure acetoin enantiomers are rarely reported. Previously, we systematically engineered the GRAS microorganism Corynebacterium glutamicum to efficiently produce (3R)-acetoin from glucose. Nevertheless, its yield and average productivity were still unsatisfactory for industrial bioprocesses.Results: In this study, cellular carbon fluxes in the acetoin producer CGR6 were further redirected toward acetoin synthesis using several metabolic engineering strategies, including blocking anaplerotic pathways, attenuating key genes of the TCA cycle and integrating additional copies of the alsSD operon into the genome. Among them, the combination of attenuation of citrate synthase and inactivation of phosphoenolpyruvate carboxylase showed a significant synergistic effect on acetoin production. Finally, the optimal engineered strain CGS11 produced a titer of 102.45 g/L acetoin with a yield of 0.419 g/g glucose at a rate of 1.86 g/L/h in a 5 L fermenter. The optical purity of the resulting (3R)-acetoin surpassed 95%.Conclusion: To the best of our knowledge, this is the highest titer of highly enantiomerically enriched (3R)-acetoin, together with a competitive product yield and productivity, achieved in a simple, green processes without expensive additives or substrates. This process therefore opens the possibility to achieve easy, efficient, economical and environmentally-friendly production of (3R)-acetoin via microbial fermentation in the near future.

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“…Acetoin (AC; 3‐hydroxy‐2‐butanone) and its derivatives have extensive applications in the food, cosmetics, agricultural and chemical industries . The chiral enantiomers l‐ (+)‐ and d‐ (−)‐AC in particular are important potential pharmaceutical intermediates .…”

Section: Introductionmentioning

confidence: 99%

In vitro biosynthesis of optically pure d‐(−)‐acetoin from meso‐2,3‐butanediol using 2,3‐butanediol dehydrogenase and NADH oxidase

Cui

Zhao

Mao

et al. 2019

J of Chemical Tech & Biotech

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BACKGROUND: Acetoin, especially the chiral L-(+)-or D-(−)-enantiomer, is a high-value industrial product that can be used as a pharmaceutical intermediate. However, the production of optically pure acetoin via conventional chemical synthesis is expensive. Classical microbial fermentations satisfy the criteria of green chemistry, but have numerous disadvantages, such as complicated process engineering, unsatisfactory titers or productivities, and difficult product separation due to the inevitable generation of by-products and overly complex media. By contrast, enzymatic biocatalysis in cell-free biosystems has numerous advantages in production of chemicals with high purity, whereas efficient enzymatic methods for the production of optically pure acetoin have rarely been reported. RESULTS: An efficient coupled two-enzyme system composed of 2,3-butanediol dehydrogenase and H 2 O-forming NADH oxidase was constructed to produce optically pure acetoin without introducing any substrate or by-product. A 2,3-butanediol dehydrogenase and three NADH oxidases were purified, characterized and assembled into different two-enzyme systems. The best system, composed of LL-NOX and CG-BDH, was then selected according to the acetoin titer. After optimization of the reaction conditions, 94.0% of meso-2,3-butanediol was converted to D-(−)-acetoin. Finally, 399.7 mmol L −1 D-(−)-acetoin with an enantiomeric excess of 91.2% was produced in 6 h without any detected by-products. CONCLUSIONS: To our best knowledge, this is the first report on the production of optically pure D-(−)-acetoin from meso-2,3-butanediol in vitro using NADH oxidase to regenerate NAD + , as well as the best substrate conversion and acetoin titer among enzymatic biosynthesis. This work therefore provides an economical and green alternative for the in vitro production of D-(−)-acetoin. Industry well characterized. 46 As shown in Fig. 2, BS-NOX, CA-NOX and LL-NOX were overexpressed in E. coli BL21 (DE3) and all the NOXs and CG-BDH were successfully produced. The molecular masses of CG-BDH and the three NOX proteins were approximately 29.5, J Chem Technol Biotechnol 2019; 94: 2547-2554

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Systematic Characterization of the Metabolism of Acetoin and Its Derivative Ligustrazine in Bacillus subtilis under Micro-Oxygen Conditions

Cited by 38 publications

References 30 publications

Flavor volatiles evolution of Chinese horse bean-chili-paste during ripening, accessed by GC×GC-TOF/MS and GC-MS-olfactometry

Flavor volatiles evolution of Chinese horse bean-chili-paste during ripening, accessed by GC×GC-TOF/MS and GC-MS-olfactometry

Engineering central pathways for industrial-level (3R)-acetoin biosynthesis in Corynebacterium glutamicum

In vitro biosynthesis of optically pure d‐(−)‐acetoin from meso‐2,3‐butanediol using 2,3‐butanediol dehydrogenase and NADH oxidase

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