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1 - Simple forms of dicarboxylic acids

T1 - Synthesis of the α,ω-dicarboxylic acid precursor of biotin by the canonical fatty acid biosynthetic pathway

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184.1005 Acetic acid.Subpart A--Foods

Mutants of E. coli defective in both phosphoenolpyruvate carboxykinase and phosphoenolpyruvate synthetase are unable to use C4-dicarboxylic acids such as succinate and malate as carbon and energy sources for growth. Revertants that have restored function for either one of these enzymes can grow in a malate-mineral medium, but at a reduced rate compared with the growth of wild-type cells. E. coli appears to use two pathways for synthesis of phosphoenolpyruvate from C4-dicarboxylic acids. One of these involves decarboxylation of oxalacetate catalyzed by phosphoenolpyruvate carboxykinase. The second pathway makes use of the combined action of malic enzyme and phosphoenolpyruvate synthetase.

T1 - Two routes for synthesis of phosphoenolpyruvate from C4-dicarboxylic acids in Escherichia coli



Suberic acid, nonanedioic acid (and its mono-unsaturated derivative:2-nonenedioic acid), decanoic acid (and its mono-unsaturated derivative:2-decenedioic acid) are present in honey () and are of special interest becausethey have long been recognized as part of the pheromone system of the honeybee (). They are producedin the mandibular glands of the queen and the worker honeybees, they regulatetheir activities in the hive.

It was shown that all these dicarboxylic acids are formed during the dryingprocess of and that thedetermination of these decomposition products may be of value in determining theage of old samples.

The higher weight dicarboxylic acids (n=10 to 21) are found in different plant lipids, particularly in what was named erroneously (triglycerides containing C20, 21, 22 and 23 dicarboxylic acids besides normal fatty acids) from the sumach tree (Rhus sp.). Among them, Thapsic acid (n=14) was isolated from the dried roots of the Mediterranean "deadly carrot", Thapsia garganica (Umbelliferae), but others, as Brassylic acid (n=11), were prepared chemically from different sources.
Brassylic acid can be produced chemically from erucic acid by ozonolysis but also by microorganisms () from . This diacid is produced on a small commercial scale in Japan for the manufacture of fragrances.
A review on the applications and the industrial biotechnology of these moleculeshas been released by Kroha K ().

A large survey of the dicarboxylic acids present in Mediterranean nuts revealed unusual components (). A total of 26 minor acids (from 2 in pecan to 8% in peanut) were determined : 8 species derived from butanedioic acid, likely in relation with photosynthesis, and 18 species with a chain from 5 to 22 carbon atoms.

Higher weight acids (>C20) are found in present at vegetal surfaces (outer bark, root epidermis). C16 to C26

Phosphoglycerides rich in isovaleric acid and long-chain iso-acids.

Decarboxylation of cubane-1,4-dicarboxylic acid was carried out viathermal degradation of the di-

N2 - Biotin synthesis requires the C7 α,ω-dicarboxylic acid, pimelic acid. Although pimelic acid was known to be primarily synthesized by a head to tail incorporation of acetate units, the synthetic mechanism was unknown. It has recently been demonstrated that in most bacteria the biotin pimelate moiety is synthesized by a modified fatty acid synthetic pathway in which the biotin synthetic intermediates are O-methyl esters disguised to resemble the canonical intermediates of the fatty acid synthetic pathway. Upon completion of the pimelate moiety, the methyl ester is cleaved. A very restricted set of bacteria have a different pathway in which the pimelate moiety is formed by cleavage of fatty acid synthetic intermediates by BioI, a member of the cytochrome P450 family.

AB - Mutants of E. coli defective in both phosphoenolpyruvate carboxykinase and phosphoenolpyruvate synthetase are unable to use C4-dicarboxylic acids such as succinate and malate as carbon and energy sources for growth. Revertants that have restored function for either one of these enzymes can grow in a malate-mineral medium, but at a reduced rate compared with the growth of wild-type cells. E. coli appears to use two pathways for synthesis of phosphoenolpyruvate from C4-dicarboxylic acids. One of these involves decarboxylation of oxalacetate catalyzed by phosphoenolpyruvate carboxykinase. The second pathway makes use of the combined action of malic enzyme and phosphoenolpyruvate synthetase.

Experiment with isovaleric acid-1-C14.

These new TTCs thus offer access to the direct synthesis of AB diblock dicarboxylic acid telechelic (co)polymers.

This volatile compound may be transiently releasedinto the air and is also a floral scent component.
4HNE, which is said to have a high cellular toxicity (, Am JClin Nutr 1993, 57, 779S), may be formed from 13-hydroperoxy-linoleic acid (13-HPODE)after several steps (reduction, H abstraction, isomerization, oxidation, cleavage) asoutlined below:

Thus, peroxidation of (n-6) fatty acids (linoleic andarachidonic acids) produces well defined compounds, 2,4-decadienal and 3-nonenal from9-hydroperoxy linoleate, hexanal and pentanal from 13-hydroperoxy linoleate, and2-heptenal from 10-hydroperoxy linoleate.
Other volatile decomposition compounds are frequently found: 2-hexenal, 2-octenal, 2,4-nonadienal,4,5-dihydroxydecenal and especially 4-hydroxy-2,3-trans-nonenal (4HNE).

T1 - Synthesis of the α,ω-dicarboxylic acid precursor of biotin by the canonical fatty acid biosynthetic pathway
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  • Dicarboxylic acids are also used in the ..

    Dicarboxylic acid - Wikipedia

  • coA which is further used in saturated fatty acid synthesis

    DICARBOXYLIC ACIDS - Lipid

  • complex forms with a dicarboxylic acid and an alkyl side ..

    Simple forms of dicarboxylic acids

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Carboxylic acid synthesis by oxidation - Organic chemistry

Biotin synthesis requires the C7 α,ω-dicarboxylic acid, pimelic acid. Although pimelic acid was known to be primarily synthesized by a head to tail incorporation of acetate units, the synthetic mechanism was unknown. It has recently been demonstrated that in most bacteria the biotin pimelate moiety is synthesized by a modified fatty acid synthetic pathway in which the biotin synthetic intermediates are O-methyl esters disguised to resemble the canonical intermediates of the fatty acid synthetic pathway. Upon completion of the pimelate moiety, the methyl ester is cleaved. A very restricted set of bacteria have a different pathway in which the pimelate moiety is formed by cleavage of fatty acid synthetic intermediates by BioI, a member of the cytochrome P450 family.

Amino Acids and Synthesis | Carboxylic Acid | Amino Acid

Biotin synthesis requires the C7 α,ω-dicarboxylic acid, pimelic acid. Although pimelic acid was known to be primarily synthesized by a head to tail incorporation of acetate units, the synthetic mechanism was unknown. It has recently been demonstrated that in most bacteria the biotin pimelate moiety is synthesized by a modified fatty acid synthetic pathway in which the biotin synthetic intermediates are O-methyl esters disguised to resemble the canonical intermediates of the fatty acid synthetic pathway. Upon completion of the pimelate moiety, the methyl ester is cleaved. A very restricted set of bacteria have a different pathway in which the pimelate moiety is formed by cleavage of fatty acid synthetic intermediates by BioI, a member of the cytochrome P450 family.

07/01/2018 · Amino Acids and Synthesis - Download ..

T1 - Synthesis and metabotropic receptor activity of the novel rigidified glutamate analogues (+)- and (-)-trans-azetidine-2,4-dicarboxylic acid and their N-methyl derivatives

2,5-Furandicarboxylic acid - Wikipedia

This may explain the absence of 2,5-furandicarboxylic acid in urine of breastfed children, and the absence of these acids in the urine of rat, pig, cow, ox, rabbit, and monkey.

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