A Short, Highly Efficient Synthesis of Coenzyme Q10

Lipshutz, Bruce H.; Mollard, Paul; Pfeiffer, Steven S.; Chrisman, Will

doi:10.1021/ja021015v

Cited by 109 publications

(49 citation statements)

References 10 publications

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“…The 10% of grown seed was transferred to 50 ml of different production media in 500 ml conical flask. The production medium PM-A contained 25 g of sucrose, 10 g of (NH 4 2. The production flasks were incubated at 30˚C with shaking at 220 rpm for 120 h. The best production medium was dosed intermittently with different concentrations of parahydroxy benzoic acid (pHBA) (5,10,20,25,40 and 50 mg/L) at 24 h [28] and with different concentration of sucrose (5%, 10%, 20%, 30% and 50%) at 48 h, 72 h solely [17].…”

Section: Optimization Of Shake Flask Fermentationmentioning

confidence: 99%

“…Recently it has received great attention for its application as therapeutic agent as well as in related fields such as a potential antioxidant [2]. CoQ 10 can be produced by chemical synthesis [3], semi-chemical synthesis [4], extraction from animal tissues [5] and microbial fermentation [6] including bacteria (e.g. Agrobacterium, Paracoccus, Cryptococcusi, Rhodobacter, Tricosporon), molds (e.g.…”

Section: Introductionmentioning

confidence: 99%

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Influence of Substrate Feeding and Process Parameters on Production of Coenzyme Q10 Using Paracoccus denitrificans ATCC 19367 Mutant Strain P-87

Tokdar¹,

Ranadive²,

Kshirsagar³

et al. 2014

ABB

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Coenzyme Q 10 (CoQ 10 ), an important antioxidant molecule playing a major role in electron transport chain, has been commercially produced by fermentation process for the use in oral nutraceutical formulations. Constructing the high-yielding CoQ 10 producing strains is a pre-requisite for cost-effective production. A superior mutant strain P-87 generated from Paracoccus denitrificans ATCC 19367, which showed 1.25-fold improvement in specific CoQ 10 content higher than the wild type strain at shake flask level, was selected to carry out the studies on CoQ 10 yield improvement through fermenter process optimization. In the course of study, initially the cane-molasses-based medium and fed-batch fermentation strategy using pHBA in combination with sucrose were standardized in shake flask using wild type strain. This strategy was subsequently translated at 2 L laboratory fermenter while optimizing the fermentation process parameters using improved mutant strain P-87. Under optimized fermentation condition, mutant strain P-87 produced 49.85 mg/L of CoQ10 having specific content of 1.63 mg/g of DCW, which was 1.36 folds higher than the specific CoQ 10 content of wild-type strain under similar optimized condition. The temperature and DO were found to be critical parameters for CoQ 10 production by mutant strain P-87. The optimum temperature was found to be 32˚C and the optimum DO concentration to be maintained throughout the fermentation cycle was found to be 30% of air saturation. Overall, a new cost-effective process has been established for the production of CoQ 10 using the cheaper substrate "cane molasses" and higher CoQ 10 producing mutant strain P-87. *Corresponding author. P. Tokdar et al.967

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Section: Optimization Of Shake Flask Fermentationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Influence of Substrate Feeding and Process Parameters on Production of Coenzyme Q10 Using Paracoccus denitrificans ATCC 19367 Mutant Strain P-87

Tokdar¹,

Ranadive²,

Kshirsagar³

et al. 2014

ABB

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“…CoQ10 can be produced by chemical [10], semi-chemical [11], and biological synthesis. Biological synthesis is the preferred route of its industrial production.…”

Section: Introductionmentioning

confidence: 99%

Combined Effect of Agitation/Aeration and Fed‐Batch Strategy on Ubiquin‐ one‐10 Production by Pseudomonas diminuta

Bule¹

2010

Chem Eng & Technol

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The effects of aeration rate and agitation speed on ubiquinone‐10 (CoQ10) submerged fermentation in a stirred‐tank reactor using Pseudomonas diminuta NCIM 2865 were investigated. CoQ10 production, biomass formation, glycerol utilization, and volumetric mass transfer coefficient (kLa) were affected by both aeration and agitation. An agitation speed of 400 rpm and aeration rate of 0.5 vvm supported the maximum production (38.56 mg L–1) of CoQ10 during batch fermentation. The fermentation run supporting maximum production had an kLa of 27.07 h–1 with the highest specific productivity and CoQ10 yield of 0.064 mg g–1h–1 and 0.96 mg g–1 glycerol, respectively. Fermentation kinetics performed under optimum aeration and agitation showed the growth‐associated constant (a = 5.067 mg g–1) to be higher than the nongrowth‐associated constant (β = 0.0242 mg g–1h–1). These results were successfully utilized for the development of fed‐batch fermentation, which increased the CoQ10 production from 38.56 mg L–1 to 42.85 mg L–1.

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“…Dietary intake of CoQ 10 is about 2-5 mg day −1 , which is inadequate for the body under pathophysiological conditions [2] . A number of methods have been developed for the synthesis of CoQ 10 [9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26] since the first industrial approach by Hideki Fukawa at Nisshin in 1974 [27] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Coenzyme Q10

Ravada¹,

Emani²,

Garaga³

et al. 2009

American J. of Infectious Diseases

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Problem statement: CoQ 10 is a key compound in ATP synthesis having wide number of health application especially for treating humans suffering from pathophysiological condition. The CoQ 10 presently available in the market is solely derived from fermentation process. A commercially viable synthetic process is yet to be realized. Approach: The researchers described a new synthetic route for the preparation of CoQ 10 (1). This new process utilized inexpensive isoprenol as a precursor for the synthesis of an early intermediate with a single isoprene unit. Another key step was the selective oxidation of trans methyl of isoprene unit as a prelude to the expansion of the side chain to decaprenyl group using solanesol. Results: Prenylation of 2, 3-dimethoxy-5-methylhydroquinone using isoprenol in presence of a Lewis acid, followed by selective oxidation of trans methyl group of isoprenyl side chain and subsequent allylic bromination yielded a bromide precursor (7). The ptoluenesulfination of the bromide followed by coupling with solanesyl bromide and de-ptoluenesulfination yielded dimethyl derivative of the CoQ 10 -quinol. Finally CAN oxidation of dimethyl quinol followed by purification yielded CoQ 10 in 13% overall yield. Conclusion: The present process achieved CoQ 10 starting from a relatively inexpensive precursor. Further improvement in the coupling reaction between 8 and solanesyl bromide may lead to a better and viable synthetic process.

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A Short, Highly Efficient Synthesis of Coenzyme Q₁₀

Abstract: The most efficient synthesis reported to date of ubiquinone (CoQ10) is described. A sequence consisting of six operations is involved which leads to crystalline material in an overall yield of >64%.

Cited by 109 publications

References 10 publications

Influence of Substrate Feeding and Process Parameters on Production of Coenzyme Q<sub>10</sub> Using <i>Paracoccus denitrificans</i> ATCC 19367 Mutant Strain P-87

Influence of Substrate Feeding and Process Parameters on Production of Coenzyme Q<sub>10</sub> Using <i>Paracoccus denitrificans</i> ATCC 19367 Mutant Strain P-87

Combined Effect of Agitation/Aeration and Fed‐Batch Strategy on Ubiquin‐ one‐10 Production by Pseudomonas diminuta

Synthesis of Coenzyme Q10

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A Short, Highly Efficient Synthesis of Coenzyme Q10

Abstract: The most efficient synthesis reported to date of ubiquinone (CoQ10) is described. A sequence consisting of six operations is involved which leads to crystalline material in an overall yield of >64%.

Cited by 109 publications

References 10 publications

Influence of Substrate Feeding and Process Parameters on Production of Coenzyme Q&lt;sub&gt;10&lt;/sub&gt; Using &lt;i&gt;Paracoccus denitrificans&lt;/i&gt; ATCC 19367 Mutant Strain P-87

Influence of Substrate Feeding and Process Parameters on Production of Coenzyme Q&lt;sub&gt;10&lt;/sub&gt; Using &lt;i&gt;Paracoccus denitrificans&lt;/i&gt; ATCC 19367 Mutant Strain P-87

Combined Effect of Agitation/Aeration and Fed‐Batch Strategy on Ubiquin‐ one‐10 Production by Pseudomonas diminuta

Synthesis of Coenzyme Q10

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A Short, Highly Efficient Synthesis of Coenzyme Q₁₀

Influence of Substrate Feeding and Process Parameters on Production of Coenzyme Q<sub>10</sub> Using <i>Paracoccus denitrificans</i> ATCC 19367 Mutant Strain P-87

Influence of Substrate Feeding and Process Parameters on Production of Coenzyme Q<sub>10</sub> Using <i>Paracoccus denitrificans</i> ATCC 19367 Mutant Strain P-87