Synthesis of Tartaric Acid

Church, James M.; Blumberg, Ruth

doi:10.1021/ie50500a030

Cited by 18 publications

(10 citation statements)

References 16 publications

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“…The 3-methyltartrates;? were synthesized by sodium tungstatecatalyzed dihydroxylation of draconic acid and mesaconic acid (Church & Blumberg, 1951).…”

mentioning

confidence: 99%

Substrate determinants of the course of tartrate dehydrogenase-catalyzed reactions

Serfózó

Tipton²

1995

Biochemistry

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The substrate specificity of tartrate dehydrogenase has been probed using a series of alternative substrates to identify the molecular interactions which determine whether a particular substrate undergoes enzyme-catalyzed decarboxylation or not. A series of 3-substituted malate analogs, in which F, Cl, Br, I, SH, or NH2 substituents were placed at the 3R- or 3S-position, was prepared, and the product resulting from the action of tartrate dehydrogenase on each compound was identified. All of the halomalates and both diastereomers of aminomalate underwent oxidative decarboxylation; both diastereomers of 3-thiomalate underwent net nonoxidative decarboxylation. The results were interpreted in terms of a model in which decarboxylation is conformationally controlled. The data are not consistent with a model which suggests that substrates assume the conformation that is necessary to avoid steric crowding between the enzyme and the substituent at the 3-position of the substrate. These data are consistent with a model in which the course of the reaction with (+)-tartrate and meso-tartrate is dictated by the coordination of the substrate hydroxyls to the active site Mn2+. However, the observed reactivities of the 3-methyltartrate diastereomers are not consistent with this model, either: (2R,3R)-3-methyltartrate undergoes oxidative decarboxylation, and (2R,3S)-3-methyltartrate undergoes simple oxidation. These results suggest that for these compounds the conformation is dictated by the positioning of the hydrophobic substituent in a specific binding pocket.(ABSTRACT TRUNCATED AT 250 WORDS)

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“…The 3-methyltartrates;? were synthesized by sodium tungstatecatalyzed dihydroxylation of draconic acid and mesaconic acid (Church & Blumberg, 1951).…”

mentioning

confidence: 99%

Substrate determinants of the course of tartrate dehydrogenase-catalyzed reactions

Serfózó

Tipton²

1995

Biochemistry

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“…A titer of 2.1 g/L tartaric acid from 20 g/L of sorbitol was obtained with this organism (Chandrashekar et al, 1999 ). However, for commercial applications, large amounts of tartaric acid are obtained today as a by-product from wine industry or by chemical conversion of maleic acid or fumaric acid (Church and Blumberg, 1951 ; Zhang et al, 2011a ).…”

Section: Metabolic Engineering For the Microbial Production Of Food Amentioning

confidence: 99%

Engineered Microorganisms for the Production of Food Additives Approved by the European Union—A Systematic Analysis

Kallscheuer

2018

Front. Microbiol.

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In the 1950s, the idea of a single harmonized list of food additives for the European Union arose. Already in 1962, the E-classification system, a robust food safety system intended to protect consumers from possible food-related risks, was introduced. Initially, it was restricted to colorants, but at later stages also preservatives, antioxidants, emulsifiers, stabilizers, thickeners, gelling agents, sweeteners, and flavorings were included. Currently, the list of substances authorized by the European Food Safety Authority (EFSA) (referred to as “E numbers”) comprises 316 natural or artificial substances including small organic molecules, metals, salts, but also more complex compounds such as plant extracts and polymers. Low overall concentrations of such compounds in natural producers due to inherent regulation mechanisms or production processes based on non-regenerative carbon sources led to an increasing interest in establishing more reliable and sustainable production platforms. In this context, microorganisms have received significant attention as alternative sources providing access to these compounds. Scientific advancements in the fields of molecular biology and genetic engineering opened the door toward using engineered microorganisms for overproduction of metabolites of their carbon metabolism such as carboxylic acids and amino acids. In addition, entire pathways, e.g., of plant origin, were functionally introduced into microorganisms, which holds the promise to get access to an even broader range of accessible products. The aim of this review article is to give a systematic overview on current efforts during construction and application of microbial cell factories for the production of food additives listed in the EU “E numbers” catalog. The review is focused on metabolic engineering strategies of industrially relevant production hosts also discussing current bottlenecks in the underlying metabolic pathways and how they can be addressed in the future.

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“…Esta síntese é realizada a partir do ácido maleico, que é uma substância derivada do petróleo. Ela consiste na hidroxilação do ácido maleico com peróxido de hidrogênio, na presença do ácido tungstíco (H 2 WO 4 ) como catalisador, (Church, 1951). O composto intermediário formado, ácido cis-epóxi succínico, é hidrolisado para a formação do ácido tartárico.A solução formada é concentrada e o produto é cristalizado em baixa temperatura, obtendo-se ácido L(+)-tartárico de alta pureza.…”

Section: 2síntese Químicaunclassified

L-Tartaric Acid: Production Technology, Economic Growth and Quality Control

Leirose¹,

Grenier-Loustalot²,

Oliveira³

2018

PTQ

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Natural substances are the basis of many types of industries and represent a growing market. The study of these products and the development of analytical methods should accompany this growth to ensure quality and provenance to consumers. An example to be discussed is the L(+)-Tartaric acid, an organic compound of molecular formula C4H6O6. This organic acid is widely applied in wine, food and pharmaceutical industry. It is obtained naturally through the fermentation of fruits, especially grape and tamarind. Synthetically, there are two ways of obtaining L(+)-tartaric acid on industrial scale. It can be synthesized by the reaction of maleic anhydride with hydrogen peroxide, which is derived from petroleum by-products. And by biotechnological synthesis, in which cis-epoxy succinic acid, also derived from petroleum, is converted into L(+)-tartaric acid by hydrolase enzyme. The market for tartaric acid is growing and is considered promising. Currently, there is a lack of legislation and specific rules that allow classification of tartaric acid according to its origin. This legal vacuum precludes quality assurance for the consumer. This lack of safety is a matter of great concern as applications of tartaric acid come directly to final consumer.

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Synthesis of Tartaric Acid

Cited by 18 publications

References 16 publications

Substrate determinants of the course of tartrate dehydrogenase-catalyzed reactions

Substrate determinants of the course of tartrate dehydrogenase-catalyzed reactions

Engineered Microorganisms for the Production of Food Additives Approved by the European Union—A Systematic Analysis

L-Tartaric Acid: Production Technology, Economic Growth and Quality Control

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