Glyoxylic acid

Last updated
Glyoxylic acid
Glyoxylic acid.png
Glyoxylic acid 3D spacefill.png
Names
Preferred IUPAC name
Oxoacetic acid [1]
Systematic IUPAC name
Oxoethanoic acid
Other names
Glyoxylic acid [1]
2-Oxoacetic acid
Formylformic acid
Identifiers
3D model (JSmol)
741891
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.005.508 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 206-058-5
25752
KEGG
PubChem CID
UNII
  • InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5) Yes check.svgY
    Key: HHLFWLYXYJOTON-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)
    Key: HHLFWLYXYJOTON-UHFFFAOYAU
  • C(=O)C(=O)O
Properties
C2H2O3
Molar mass 74.035 g·mol−1
Density 1.384 g/mL
Melting point 80 °C (176 °F; 353 K) [2]
Boiling point 111 °C (232 °F; 384 K)
Acidity (pKa)3.18, [3] 3.32 [4]
Related compounds
Other anions
glyoxylate
formic acid
acetic acid
glycolic acid
oxalic acid
propionic acid
pyruvic acid
Related compounds
 acetaldehyde
glyoxal
glycolaldehyde
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Glyoxylic acid or oxoacetic acid is an organic compound. Together with acetic acid, glycolic acid, and oxalic acid, glyoxylic acid is one of the C2 carboxylic acids. It is a colourless solid that occurs naturally and is useful industrially.

Contents

Structure and nomenclature

The structure of glyoxylic acid is shown as having an aldehyde functional group. The aldehyde is only a minor component of the form most prevalent in some situations. Instead, glyoxalic acid often exists as a hydrate or a cyclic dimer. For example, in the presence of water, the carbonyl rapidly converts to a geminal diol (described as the "monohydrate"). The equilibrium constant (K) is 300 for the formation of dihydroxyacetic acid at room temperature: [5] Dihydroxyacetic acid has been characterized by X-ray crystallography. [6]

Glyoxylic acid hydration.png

In aqueous solution, this monohydrate exists in equilibrium with a hemiacylal dimer form: [7]

Glyoxylic acid hydrate dimerization.png

In isolation, the aldehyde structure has as a major conformer a cyclic hydrogen-bonded structure with the aldehyde carbonyl in close proximity to the carboxyl hydrogen: [8]

Glyoxylic acid H-bonded.png

The Henry's law constant of glyoxylic acid is KH = 1.09 × 104 × exp[(40.0 × 103/R) × (1/T − 1/298)]. [9]

Preparations

The conjugate base of glyoxylic acid is known as glyoxylate and is the form that the compound exists in solution at neutral pH. Glyoxylate is the byproduct of the amidation process in biosynthesis of several amidated peptides.

For the historical record, glyoxylic acid was prepared from oxalic acid electrosynthetically: [10] [11] in organic synthesis, lead dioxide cathodes were applied for preparing glyoxylic acid from oxalic acid in a sulfuric acid electrolyte. [12]

GlyoxalicAcidElectrosyn.png

Hot nitric acid can oxidize glyoxal to glyoxylic; however this reaction is highly exothermic and prone to thermal runaway. In addition, oxalic acid is the main side product.

Also, ozonolysis of maleic acid is effective. [7]

Biological role

Glyoxylate is an intermediate of the glyoxylate cycle, which enables organisms, such as bacteria, [13] fungi, and plants [14] to convert fatty acids into carbohydrates. The glyoxylate cycle is also important for induction of plant defense mechanisms in response to fungi. [15] The glyoxylate cycle is initiated through the activity of isocitrate lyase, which converts isocitrate into glyoxylate and succinate. Research is being done to co-opt the pathway for a variety of uses such as the biosynthesis of succinate. [16]

In humans

Glyoxylate is produced via two pathways: through the oxidation of glycolate in peroxisomes or through the catabolism of hydroxyproline in mitochondria. [17] In the peroxisomes, glyoxylate is converted into glycine by AGT1 or into oxalate by glycolate oxidase. In the mitochondria, glyoxylate is converted into glycine by AGT2 or into glycolate by glyoxylate reductase. A small amount of glyoxylate is converted into oxalate by cytoplasmic lactate dehydrogenase. [18]

Oxalate and glyoxylate metabolism in hepatocytes. AGT1 and 2, alanine:glyoxylate aminotransferase 1 and 2; GO, glycolate oxidase; GR, glyoxylate reductase; HKGA, 4-hydroxy-2-ketoglutarate lyase; LDH, lactate dehydrogenase Glyoxylate metabolism in hepatocytes.jpg
Oxalate and glyoxylate metabolism in hepatocytes. AGT1 and 2, alanine:glyoxylate aminotransferase 1 and 2; GO, glycolate oxidase; GR, glyoxylate reductase; HKGA, 4-hydroxy-2-ketoglutarate lyase; LDH, lactate dehydrogenase

In plants

In addition to being an intermediate in the glyoxylate cycle, glyoxylate is also an important intermediate in the photorespiration pathway. Photorespiration is a result of the side reaction of RuBisCO with O2 instead of CO2. While at first considered a waste of energy and resources, photorespiration has been shown to be an important method of regenerating carbon and CO2, removing toxic phosphoglycolate, and initiating defense mechanisms. [19] [20] In photorespiration, glyoxylate is converted from glycolate through the activity of glycolate oxidase in the peroxisome. It is then converted into glycine through parallel actions by SGAT and GGAT, which is then transported into the mitochondria. [21] [20] It has also been reported that the pyruvate dehydrogenase complex may play a role in glycolate and glyoxylate metabolism. [22]

Basic overview of photorespiration in Arabidopsis. GGAT, glyoxylate:glutamate aminotransferase; GLYK, glycerate kinase; GO, glycolate oxidase; HPR, hydroxypyruvate reductase; PGLP, phosphoglycolate phosphatase; Rubisco, RuBP carboxylase/oxygenase; SGAT, serine:glyoxylate aminotransferase; SHM, serine hydroxymethyltransferase Photorespiration in arabidopsis.jpg
Basic overview of photorespiration in Arabidopsis. GGAT, glyoxylate:glutamate aminotransferase; GLYK, glycerate kinase; GO, glycolate oxidase; HPR, hydroxypyruvate reductase; PGLP, phosphoglycolate phosphatase; Rubisco, RuBP carboxylase/oxygenase; SGAT, serine:glyoxylate aminotransferase; SHM, serine hydroxymethyltransferase

Disease relevance

Diabetes

Glyoxylate is thought to be a potential early marker for Type II diabetes. [23] One of the key conditions of diabetes pathology is the production of advanced glycation end-products (AGEs) caused by the hyperglycemia. [24] AGEs can lead to further complications of diabetes, such as tissue damage and cardiovascular disease. [25] They are generally formed from reactive aldehydes, such as those present on reducing sugars and alpha-oxoaldehydes. In a study, glyoxylate levels were found to be significantly increased in patients who were later diagnosed with Type II diabetes. [23] The elevated levels were found sometimes up to three years before the diagnosis, demonstrating the potential role for glyoxylate to be an early predictive marker.

Nephrolithiasis

Glyoxylate is involved in the development of hyperoxaluria, a key cause of nephrolithiasis (commonly known as kidney stones). Glyoxylate is both a substrate and inductor of sulfate anion transporter-1 (sat-1), a gene responsible for oxalate transportation, allowing it to increase sat-1 mRNA expression and as a result oxalate efflux from the cell. The increased oxalate release allows the buildup of calcium oxalate in the urine, and thus the eventual formation of kidney stones. [18]

The disruption of glyoxylate metabolism provides an additional mechanism of hyperoxaluria development. Loss of function mutations in the HOGA1 gene leads to a loss of the 4-hydroxy-2-oxoglutarate aldolase, an enzyme in the hydroxyproline to glyoxylate pathway. The glyoxylate resulting from this pathway is normally stored away to prevent oxidation to oxalate in the cytosol. The disrupted pathway, however, causes a buildup of 4-hydroxy-2-oxoglutarate which can also be transported to the cytosol and converted into glyoxylate through a different aldolase. These glyoxylate molecules can be oxidized into oxalate increasing its concentration and causing hyperoxaluria. [17]

Reactions and uses

Glyoxylic acid is about ten times stronger an acid than acetic acid, with an acid dissociation constant of 4.7 × 10−4 (pKa = 3.32):

OCHCO2H ⇌OCHCO−
2 + H+

With concentrated base, glyoxylic acid disproportionates via a Cannizzaro reaction, forming hydroxyacetic acid and oxalic acid:[ citation needed ]

2 OCHCO2H + H2O → HOCH2CO2H + HO2CCO2H

Glyoxylic acid gives heterocycles upon condensation with urea and 1,2-diaminobenzene.

Phenol derivatives

In general, glyoxylic acid undergoes an electrophilic aromatic substitution reaction with phenols, a versatile step in the synthesis of several other compounds.

The immediate product with phenol itself is 4-hydroxymandelic acid. This species reacts with ammonia to give hydroxyphenylglycine, a precursor to the drug amoxicillin. Reduction of the 4-hydroxymandelic acid gives 4-hydroxyphenylacetic acid, a precursor to the drug atenolol.

The sequence of reactions, in which glyoxylic acid reacts with guaiacol the phenolic component followed by oxidation and decarboxylation, provides a route to vanillin as a net formylation process. [7] [26] [27]

Hopkins Cole reaction

Glyoxylic acid is a component of the Hopkins–Cole reaction, used to check for the presence of tryptophan in proteins. [28]

Environmental chemistry

Glyoxylic acid is one of several ketone- and aldehyde-containing carboxylic acids that together are abundant in secondary organic aerosols. In the presence of water and sunlight, glyoxylic acid can undergo photochemical oxidation. Several different reaction pathways can ensue, leading to various other carboxylic acid and aldehyde products. [29]

Safety

The compound is not very toxic with an LD50 for rats of 2500 mg/kg.

But a recent experiment shows that it is toxic. See https://karger.com/cnd/article/12/2/112/827730/Acute-Kidney-Injury-following-Exposure-to.

See also

Related Research Articles

<span class="mw-page-title-main">Citric acid cycle</span> Interconnected biochemical reactions releasing energy

The citric acid cycle—also known as the Krebs cycle, Szent-Györgyi-Krebs cycle or the TCA cycle (tricarboxylic acid cycle)—is a series of biochemical reactions to release the energy stored in nutrients through the oxidation of acetyl-CoA derived from carbohydrates, fats, and proteins. The chemical energy released is available under the form of ATP. The Krebs cycle is used by organisms that respire (as opposed to organisms that ferment) to generate energy, either by anaerobic respiration or aerobic respiration. In addition, the cycle provides precursors of certain amino acids, as well as the reducing agent NADH, that are used in numerous other reactions. Its central importance to many biochemical pathways suggests that it was one of the earliest components of metabolism. Even though it is branded as a 'cycle', it is not necessary for metabolites to follow only one specific route; at least three alternative segments of the citric acid cycle have been recognized.

<span class="mw-page-title-main">Metabolism</span> Set of chemical reactions in organisms

Metabolism is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cellular processes; the conversion of food to building blocks of proteins, lipids, nucleic acids, and some carbohydrates; and the elimination of metabolic wastes. These enzyme-catalyzed reactions allow organisms to grow and reproduce, maintain their structures, and respond to their environments. The word metabolism can also refer to the sum of all chemical reactions that occur in living organisms, including digestion and the transportation of substances into and between different cells, in which case the above described set of reactions within the cells is called intermediary metabolism.

<span class="mw-page-title-main">Peroxisome</span> Type of organelle

A peroxisome (IPA:[pɛɜˈɹɒksɪˌsoʊm]) is a membrane-bound organelle, a type of microbody, found in the cytoplasm of virtually all eukaryotic cells. Peroxisomes are oxidative organelles. Frequently, molecular oxygen serves as a co-substrate, from which hydrogen peroxide (H2O2) is then formed. Peroxisomes owe their name to hydrogen peroxide generating and scavenging activities. They perform key roles in lipid metabolism and the reduction of reactive oxygen species.

<span class="mw-page-title-main">Succinic acid</span> Dicarboxylic acid

Succinic acid is a dicarboxylic acid with the chemical formula (CH2)2(CO2H)2. In living organisms, succinic acid takes the form of an anion, succinate, which has multiple biological roles as a metabolic intermediate being converted into fumarate by the enzyme succinate dehydrogenase in complex 2 of the electron transport chain which is involved in making ATP, and as a signaling molecule reflecting the cellular metabolic state.

<span class="mw-page-title-main">Photorespiration</span> Process in plant metabolism

Photorespiration (also known as the oxidative photosynthetic carbon cycle or C2 cycle) refers to a process in plant metabolism where the enzyme RuBisCO oxygenates RuBP, wasting some of the energy produced by photosynthesis. The desired reaction is the addition of carbon dioxide to RuBP (carboxylation), a key step in the Calvin–Benson cycle, but approximately 25% of reactions by RuBisCO instead add oxygen to RuBP (oxygenation), creating a product that cannot be used within the Calvin–Benson cycle. This process lowers the efficiency of photosynthesis, potentially lowering photosynthetic output by 25% in C3 plants. Photorespiration involves a complex network of enzyme reactions that exchange metabolites between chloroplasts, leaf peroxisomes and mitochondria.

<span class="mw-page-title-main">Oxalic acid</span> Simplest dicarboxylic acid

Oxalic acid is an organic acid with the systematic name ethanedioic acid and chemical formula HO−C(=O)−C(=O)−OH, also written as (COOH)2 or (CO2H)2 or H2C2O4. It is the simplest dicarboxylic acid. It is a white crystalline solid that forms a colorless solution in water. Its name comes from the fact that early investigators isolated oxalic acid from flowering plants of the genus Oxalis, commonly known as wood-sorrels. It occurs naturally in many foods. Excessive ingestion of oxalic acid or prolonged skin contact can be dangerous.

C<sub>3</sub> carbon fixation Series of interconnected biochemical reactions

C3 carbon fixation is the most common of three metabolic pathways for carbon fixation in photosynthesis, the other two being C4 and CAM. This process converts carbon dioxide and ribulose bisphosphate (RuBP, a 5-carbon sugar) into two molecules of 3-phosphoglycerate through the following reaction:

<span class="mw-page-title-main">Oxaloacetic acid</span> Organic compound

Oxaloacetic acid (also known as oxalacetic acid or OAA) is a crystalline organic compound with the chemical formula HO2CC(O)CH2CO2H. Oxaloacetic acid, in the form of its conjugate base oxaloacetate, is a metabolic intermediate in many processes that occur in animals. It takes part in gluconeogenesis, the urea cycle, the glyoxylate cycle, amino acid synthesis, fatty acid synthesis and the citric acid cycle.

Toxication, toxification or toxicity exaltation is the conversion of a chemical compound into a more toxic form in living organisms or in substrates such as soil or water. The conversion can be caused by enzymatic metabolism in the organisms, as well as by abiotic chemical reactions. While the parent drug are usually less active, both the parent drug and its metabolite can be chemically active and cause toxicity, leading to mutagenesis, teratogenesis, and carcinogenesis. Different classes of enzymes, such as P450-monooxygenases, epoxide hydrolase, or acetyltransferases can catalyze the process in the cell, mostly in the liver.

<span class="mw-page-title-main">Glycolic acid</span> Chemical compound

Glycolic acid is a colorless, odorless and hygroscopic crystalline solid, highly soluble in water. It is used in various skin-care products. Glycolic acid is widespread in nature. A glycolate is a salt or ester of glycolic acid.

<span class="mw-page-title-main">Glyoxylate cycle</span> Series of interconnected biochemical reactions

The glyoxylate cycle, a variation of the tricarboxylic acid cycle, is an anabolic pathway occurring in plants, bacteria, protists, and fungi. The glyoxylate cycle centers on the conversion of acetyl-CoA to succinate for the synthesis of carbohydrates. In microorganisms, the glyoxylate cycle allows cells to use two carbons, such as acetate, to satisfy cellular carbon requirements when simple sugars such as glucose or fructose are not available. The cycle is generally assumed to be absent in animals, with the exception of nematodes at the early stages of embryogenesis. In recent years, however, the detection of malate synthase (MS) and isocitrate lyase (ICL), key enzymes involved in the glyoxylate cycle, in some animal tissue has raised questions regarding the evolutionary relationship of enzymes in bacteria and animals and suggests that animals encode alternative enzymes of the cycle that differ in function from known MS and ICL in non-metazoan species.

<span class="mw-page-title-main">Glycerate dehydrogenase</span>

In enzymology, a glycerate dehydrogenase (EC 1.1.1.29) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Glyoxylate reductase</span> Enzyme

Glyoxylate reductase, first isolated from spinach leaves, is an enzyme that catalyzes the reduction of glyoxylate to glycolate, using the cofactor NADH or NADPH.

<span class="mw-page-title-main">Oxalate oxidase</span>

In enzymology, an oxalate oxidase (EC 1.2.3.4) is an oxalate degrading enzyme that catalyzes the chemical reaction:

<span class="mw-page-title-main">Isocitrate lyase</span>

Isocitrate lyase, or ICL, is an enzyme in the glyoxylate cycle that catalyzes the cleavage of isocitrate to succinate and glyoxylate. Together with malate synthase, it bypasses the two decarboxylation steps of the tricarboxylic acid cycle and is used by bacteria, fungi, and plants.

<span class="mw-page-title-main">Malate synthase</span> Class of enzymes

In enzymology, a malate synthase (EC 2.3.3.9) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Druse (botany)</span>

A druse is a group of crystals of calcium oxalate, silicates, or carbonates present in plants, and are thought to be a defense against herbivory due to their toxicity. Calcium oxalate (Ca(COO)2, CaOx) crystals are found in algae, angiosperms and gymnosperms in a total of more than 215 families. These plants accumulate oxalate in the range of 3–80% (w/w) of their dry weight through a biomineralization process in a variety of shapes. Araceae have numerous druses, multi-crystal druses and needle-shaped raphide crystals of CaOx present in the tissue. Druses are also found in leaves and bud scales of Prunus, Rosa, Allium, Vitis, Morus and Phaseolus.

Glyoxylate and dicarboxylate metabolism describes a variety of reactions involving glyoxylate or dicarboxylates. Glyoxylate is the conjugate base of glyoxylic acid, and within a buffered environment of known pH such as the cell cytoplasm these terms can be used almost interchangeably, as the gain or loss of a hydrogen ion is all that distinguishes them, and this can occur in the aqueous environment at any time. Likewise dicarboxylates are the conjugate bases of dicarboxylic acids, a general class of organic compounds containing two carboxylic acid groups, such as oxalic acid or succinic acid.

<span class="mw-page-title-main">Hydroxyacid oxidase (glycolate oxidase) 1</span> Protein-coding gene in the species Homo sapiens

Hydroxyacid oxidase 1 is a protein that in humans is encoded by the HAO1 gene.

<span class="mw-page-title-main">2-Phosphoglycolate</span> Chemical compound

2-Phosphoglycolate (chemical formula C2H2O6P3-; also known as phosphoglycolate, 2-PG, or PG) is a natural metabolic product of the oxygenase reaction mediated by the enzyme ribulose 1,5-bisphosphate carboxylase (RuBisCo).

References

  1. 1 2 "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 748. doi:10.1039/9781849733069-FP001. ISBN   978-0-85404-182-4.
  2. ↑ Merck Index, 11th Edition, 4394
  3. ↑ Dissociation Constants Of Organic Acids and Bases (600 compounds), http://zirchrom.com/organic.htm.
  4. ↑ pKa Data Compiled by R. Williams, "Archived copy" (PDF). Archived from the original (PDF) on 2010-06-02. Retrieved 2010-06-02.{{cite web}}: CS1 maint: archived copy as title (link).
  5. ↑ Sørensen, P. E.; Bruhn, K.; Lindeløv, F. (1974). "Kinetics and equilibria for the reversible hydration of the aldehyde group in glyoxylic acid". Acta Chem. Scand. 28: 162–168. doi: 10.3891/acta.chem.scand.28a-0162 .
  6. ↑ Czapik, Agnieszka; Gdaniec, Maria (2007). "Quinoxaline–dihydroxyacetic acid (1/1)". Acta Crystallographica Section E: Structure Reports Online. 63 (7): o3081. doi:10.1107/S1600536807025792.
  7. 1 2 3 Georges Mattioda and Yani Christidis “Glyoxylic Acid” Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi : 10.1002/14356007.a12_495
  8. ↑ Redington, Richard L.; Liang, Chin-Kang Jim (1984). "Vibrational spectra of glyoxylic acid monomers". Journal of Molecular Spectroscopy. 104 (1): 25–39. Bibcode:1984JMoSp.104...25R. doi:10.1016/0022-2852(84)90242-X.
  9. ↑ Ip, H. S. Simon; Huang, X. H. Hilda; Yu, Jian Zhen (2009). "Effective Henry's law constants of glyoxal, glyoxylic acid, and glycolic acid" (PDF). Geophysical Research Letters. 36 (1): L01802. Bibcode:2009GeoRL..36.1802I. doi:10.1029/2008GL036212. S2CID   129747490.
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  13. ↑ Holms WH (1987). "Control of flux through the citric acid cycle and the glyoxylate bypass in Escherichia coli". Biochem Soc Symp. 54: 17–31. PMID   3332993.
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  15. ↑ Dubey, Mukesh K.; Broberg, Anders; Sooriyaarachchi, Sanjeewani; Ubhayasekera, Wimal; Jensen, Dan Funck; Karlsson, Magnus (September 2013). "The glyoxylate cycle is involved in pleotropic phenotypes, antagonism and induction of plant defence responses in the fungal biocontrol agent Trichoderma atroviride". Fungal Genetics and Biology. 58–59: 33–41. doi:10.1016/j.fgb.2013.06.008. ISSN   1087-1845. PMID   23850601.
  16. ↑ Zhu, Li-Wen; Li, Xiao-Hong; Zhang, Lei; Li, Hong-Mei; Liu, Jian-Hua; Yuan, Zhan-Peng; Chen, Tao; Tang, Ya-Jie (November 2013). "Activation of glyoxylate pathway without the activation of its related gene in succinate-producing engineered Escherichia coli". Metabolic Engineering. 20: 9–19. doi:10.1016/j.ymben.2013.07.004. ISSN   1096-7176. PMID   23876414.
  17. 1 2 Belostotsky, Ruth; Pitt, James Jonathon; Frishberg, Yaacov (2012-12-01). "Primary hyperoxaluria type III—a model for studying perturbations in glyoxylate metabolism". Journal of Molecular Medicine. 90 (12): 1497–1504. doi:10.1007/s00109-012-0930-z. hdl: 11343/220107 . ISSN   0946-2716. PMID   22729392. S2CID   11549218.
  18. 1 2 Schnedler, Nina; Burckhardt, Gerhard; Burckhardt, Birgitta C. (March 2011). "Glyoxylate is a substrate of the sulfate-oxalate exchanger, sat-1, and increases its expression in HepG2 cells". Journal of Hepatology. 54 (3): 513–520. doi:10.1016/j.jhep.2010.07.036. ISSN   0168-8278. PMID   21093948.
  19. ↑ "photorespiration". Archived from the original on 2006-12-11. Retrieved 2017-03-09.
  20. 1 2 Peterhansel, Christoph; Horst, Ina; Niessen, Markus; Blume, Christian; Kebeish, Rashad; Kürkcüoglu, Sophia; Kreuzaler, Fritz (2010-03-23). "Photorespiration". The Arabidopsis Book. 8: e0130. doi:10.1199/tab.0130. ISSN   1543-8120. PMC   3244903 . PMID   22303256.
  21. ↑ Zhang, Zhisheng; Mao, Xingxue; Ou, Juanying; Ye, Nenghui; Zhang, Jianhua; Peng, Xinxiang (January 2015). "Distinct photorespiratory reactions are preferentially catalyzed by glutamate:glyoxylate and serine:glyoxylate aminotransferases in rice". Journal of Photochemistry and Photobiology B: Biology. 142: 110–117. doi:10.1016/j.jphotobiol.2014.11.009. ISSN   1011-1344. PMID   25528301.
  22. ↑ Blume, Christian; Behrens, Christof; Eubel, Holger; Braun, Hans-Peter; Peterhansel, Christoph (November 2013). "A possible role for the chloroplast pyruvate dehydrogenase complex in plant glycolate and glyoxylate metabolism". Phytochemistry. 95: 168–176. Bibcode:2013PChem..95..168B. doi:10.1016/j.phytochem.2013.07.009. ISSN   0031-9422. PMID   23916564.
  23. 1 2 Nikiforova, Victoria J.; Giesbertz, Pieter; Wiemer, Jan; Bethan, Bianca; Looser, Ralf; Liebenberg, Volker; Ruiz Noppinger, Patricia; Daniel, Hannelore; Rein, Dietrich (2014). "Glyoxylate, a New Marker Metabolite of Type 2 Diabetes". Journal of Diabetes Research. 2014: 685204. doi: 10.1155/2014/685204 . ISSN   2314-6745. PMC   4265698 . PMID   25525609.
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  25. ↑ Piarulli, Francesco; Sartore, Giovanni; Lapolla, Annunziata (April 2013). "Glyco-oxidation and cardiovascular complications in type 2 diabetes: a clinical update". Acta Diabetologica. 50 (2): 101–110. doi:10.1007/s00592-012-0412-3. ISSN   0940-5429. PMC   3634985 . PMID   22763581.
  26. ↑ Fatiadi, Alexander; Schaffer, Robert (1974). "An Improved Procedure for Synthesis of DL-4-Hydroxy-3-methoxymandelic Acid (DL-"Vanillyl"-mandelic Acid, VMA)". Journal of Research of the National Bureau of Standards Section A. 78A (3): 411–412. doi: 10.6028/jres.078A.024 . PMC   6742820 . PMID   32189791.
  27. ↑ Kamlet, Jonas; Mathieson, Olin (1953). Manufacture of vanillin and its homologues U.S. Patent 2,640,083 (PDF). U.S. Patent Office.
  28. ↑ R.A. Joshi (2006). Question Bank of Biochemistry. New Age International. p. 64. ISBN   978-81-224-1736-4.
  29. ↑ Eugene, Alexis J.; Xia, Sha-Sha; Guzman, Marcelo I. (2016). "Aqueous Photochemistry of Glyoxylic Acid". J. Phys. Chem. A. 120 (21): 3817–3826. Bibcode:2016JPCA..120.3817E. doi: 10.1021/acs.jpca.6b00225 . PMID   27192089.
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