Optimization of Biocatalyst Specific Activity for Glycolic Acid Production

Ben‐Bassat, Arie; Walls, Alison M.; Plummer, Matthew A.; Sigmund, Amy E.; Spillan, William L.; DiCosimo, Robert

doi:10.1002/adsc.200800228

Cited by 16 publications

(10 citation statements)

References 17 publications

(11 reference statements)

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“…Reacting formaldehyde with carbon monoxide in the presence of an acid catalyst, such as HF, also produces glycolic acid. It can be made using glycolonitrile in an enzymatic process [12,144]. Due to the extremely hazardous nature of reactants involved in these routes, other ways to produce glycolic acid have been investigated.…”

Section: Glycolic Acidmentioning

confidence: 99%

Catalytic Conversion of Lignocellulosic Biomass to Value-Added Organic Acids in Aqueous Media

Lin

Liu

et al. 2014

Green Chemistry and Sustainable Technology

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The transition from today's fossil-based economy to a sustainable economy based on renewable biomass is driven by the concern of climate change and anticipation of dwindling fossil resources. Although biofuels are the central theme of the transition, biomass resources cannot completely replace petroleum. It is projected that biofuels can only supply up to 30 % of today's transportation fuel market even if all available domestic biomass resources are used for the production of liquid fuels. Therefore, transformation of biomass into high-value-added chemicals is advantageous to secure optimal use of the abundant, but limited, biomass resources from the economical and ecological perspective. Industry is increasingly considering bio-based chemical production as an attractive area for investment. The potential for chemical and polymer production from biomass is substantial. The US Department of Energy recently issued a report which listed 12 chemical building blocks considered as potential building blocks for the future. Organic acids (e.g., succinic, lactic, levulinic acid, etc.) are among the widely spread ''platform-molecules,'' which may be further converted into possibly derivable high-value-added chemicals. The transition from a fossil chemical industry to a renewable chemical industry will likewise depend on our ability to focus research and development efforts on the most promising alternatives. In this chapter, we review the emerging technologies on catalytic conversion of biomass to value-added organic acids in aqueous media.

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Section: Glycolic Acidmentioning

confidence: 99%

Catalytic Conversion of Lignocellulosic Biomass to Value-Added Organic Acids in Aqueous Media

Lin

Liu

et al. 2014

Green Chemistry and Sustainable Technology

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“…Entrapment seemed to be a better choice for immobilization [1,4,12,17], and immobilization of Alcaligenes faecalis ECU0401 cells in calcium alginate beads was used for further racemic mandelonitrile hydrolysis. To investigate the effect of recycling on the degree of mandelonitrile conversion, biotransformation reaction was carried out both with free cells and alginate-entrapped cells in batch mode.…”

Section: Efficient Biocatalyst Recyclingmentioning

confidence: 99%

“…Production of (R)-(-)-mandelic acid can be achieved by physicochemical methods [13] as well as by different enzymatic routes. There is a considerable industrial interest in enzymatic conversion of various nitriles owing to the desirability of conducting such conversions under mild conditions that would not alter other labile reactive groups [4,6,7,22,23,27]. Biocatalytic hydrolysis of nitriles has been shown to proceed through two distinct pathways: in the presence of a nitrilase (EC 3.5.5.1) [2,19,36,39], nitriles undergo direct bioconversion to the corresponding carboxylic acids and ammonia; whereas a nitrile hydratase (EC 4.2.1.84) [3,29] catalyzes the hydration of nitriles followed by the biotransformation into the corresponding acids with the aid of an amidase (EC 3.5.14) [34,38].…”

Section: Introductionmentioning

confidence: 99%

Biocatalytic synthesis of (R)-(−)-mandelic acid from racemic mandelonitrile by cetyltrimethylammonium bromide-permeabilized cells of Alcaligenes faecalis ECU0401

Zhang

et al. 2010

J Ind Microbiol Biotechnol

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The nitrilase from Alcaligenes faecalis ECU0401 belongs to the category of arylacetonitrilase, which could hydrolyze 2-chloromandelonitrile, 3,4-dimethoxyphenylacetonitrile, mandelonitrile, and phenylacetonitrile into the corresponding arylacetic acids. To overcome the permeability barrier and prepare whole cell biocatalysts with high activities, permeabilization of Alcaligenes faecalis ECU0401 in relation to nitrilase activity was optimized by using cetyltrimethylammonium bromide (CTAB) as permeabilizing agent. The nitrilase activity from Alcaligenes faecalis ECU0401 increased 4.5-fold when the cells were permeabilized with 0.3% (w/v) CTAB for 20 min at 25 degrees C and pH 6.5. Consequently, almost all the mandelonitrile was consumed and converted to (R)-(-)-mandelic acid with greater than 99.9% enantiomeric excess (e.e.) by the CTAB-permeabilized cells. The permeability barrier has been significantly reduced in the hydrolysis of mandelonitrile by using CTAB-permeabilized cells and a dynamic resolution was successfully achieved, giving a 100% theoretical yield of (R)-(-)-mandelic acid. Efficient biocatalyst recycling was achieved as a result of cell immobilization in calcium alginate, with a product-to-biocatalyst ratio of 3.82 g (R)-(-)-mandelic acid g(-1) dry cell weight (dcw) cell after 20 cycles of repeated use.

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“…Many of the nitrilases from microorganisms have been applied successfully in industry. For example, the nitrilase from Alcaligenes faecalis ATCC8750 [12] is an effective catalyst for the stereoselective hydrolysis of mandelonitrile to (R)-(−)-mandelic acid and the nitrilase from Acidovorax facilis 72W [13] can convert glycolonitrile to glycolic acid with high efficiency.…”

Section: Introductionmentioning

confidence: 99%

A New Nitrilase-Producing Strain Named Rhodobacter sphaeroides LHS-305: Biocatalytic Characterization and Substrate Specificity

Yang

Wang

Wei

2011

Appl Biochem Biotechnol

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The characteristics of the new nitrilase-producing strain Rhodobacter sphaeroides LHS-305 were investigated. By investigating several parameters influencing nitrilase production, the specific cell activity was ultimately increased from 24.5 to 75.0 μmol g(-1) min(-1), and hereinto, the choice of inducer proved the most important factor. The aromatic nitriles (such as 3-cyanopyridine and benzonitrile) were found to be the most favorable substrates of the nitrilase by analyzing the substrate spectrum. It was speculated that the unsaturated carbon atom attached to the cyano group was crucial for this type of nitrilase. The value of apparent K (m), substrate inhibition constant, and product inhibition constant of the nitrilase against 3-cyanopyridine were 4.5 × 10(-2), 29.2, and 8.6 × 10(-3) mol L(-1), respectively. When applied in nicotinic acid preparation, the nitrilase is able to hydrolyze 200 mmol L(-1) 3-cyanopyridine with 93% conversion rate in 13 h by 6.1 g L(-1) cells (dry cell weight).

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Optimization of Biocatalyst Specific Activity for Glycolic Acid Production

Cited by 16 publications

References 17 publications

Catalytic Conversion of Lignocellulosic Biomass to Value-Added Organic Acids in Aqueous Media

Catalytic Conversion of Lignocellulosic Biomass to Value-Added Organic Acids in Aqueous Media

Biocatalytic synthesis of (R)-(−)-mandelic acid from racemic mandelonitrile by cetyltrimethylammonium bromide-permeabilized cells of Alcaligenes faecalis ECU0401

A New Nitrilase-Producing Strain Named Rhodobacter sphaeroides LHS-305: Biocatalytic Characterization and Substrate Specificity

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