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Isocitric acid

From Wikipedia, the free encyclopedia

Isocitric acid
Names
IUPAC name
1-Hydroxypropane-1,2,3-tricarboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.005.713 Edit this at Wikidata
KEGG
MeSH Isocitrate
UNII
  • InChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13) checkY
    Key: ODBLHEXUDAPZAU-UHFFFAOYSA-N checkY
  • InChI=1/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13)
    Key: ODBLHEXUDAPZAU-UHFFFAOYAX
  • O=C(O)C(CC(=O)O)C(O)C(=O)O
Properties
C6H8O7
Molar mass 192.124
Melting point 105 °C (221 °F; 378 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Isocitric acid is a structural isomer of citric acid. Since citric acid and isocitric acid are structural isomers, they share similar physical and chemical properties. Due to these similar properties, it is difficult to separate the isomers.[1] Salts and esters of isocitric acid are known as isocitrates. The isocitrate anion is a substrate of the citric acid cycle. Isocitrate is formed from citrate with the help of the enzyme aconitase, and is acted upon by isocitrate dehydrogenase.

Isocitric acid is commonly used as a marker to detect the authenticity and quality of fruit products, most often citrus juices. In authentic orange juice, for example, the ratio of citric acid to D-isocitric acid is usually less than 130. An isocitric acid value higher than this may be indicative of fruit juice adulteration.[2]

Isocitric acid has largely been used as a biochemical agent due to limited amounts.[3] However, isocitric acid has been shown to have pharmaceutical and therapeutic effects. Isocitric acid has been shown to effectively treat iron deficient anemia.[1] Additionally, isocitric acid could be used to treat Parkinson's disease.[3] Yarrowia lipolytica can be used to produce isocitric acid and is inexpensive compared to other methods. Furthermore, other methods produce unequal amounts of citric acid to isocitric acid ratio, mostly producing citric acid. Use of Yarrowia lipolytica produces a better yield, making equal amounts of citric acid to isocitric acid.[3]

YouTube Encyclopedic

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  • Citric Acid Cycle Mnemonic (B: 2/5): Biochem Tutorial: Krebs cycle, substrates, citrate, isocitrate
  • 28. Kevin Ahern's Biochemistry - Citric Acid Cycle II
  • MECHANISM OF AEROBIC RESPIRATION_PART 02
  • Κύκλος Κιτρικού Οξέος (Krebs citric acid cycle) - DigiClass
  • Magic plant House leek

Transcription

Our previous tutorials discussed glycolysis and the transition from pyruvate to the citric acid cycle. The substrates of the citric krebs cycle can be remembered by this mnemonic: Access is the only key to suck a sucky few more orphan cities or Access “is C” only “key to” |suck A| “suck E” few more orphan cities. Access means “cis-Aconitate” “is C” means “IsoCitrate” “only” means “Oxalosuccinate” “key to” means “a-Ketoglutarate” “suck A” means “Succinyl-CoA” “sucky” means Succinate “Few” means “Fumarate” “More” means “malate” “Orphan” means “Oxaloacetate” “Cities” means “Citrate” This mnemonic can loop endlessley, just like the citric acid cycle Access is the only key to suck a “sucky” few more orphan city access is the only key to suck a sucky few more orphan cities. Our next biochemistry tutorial explains the enyzmes involved, and how you can guess their names from the nearby substrates. HelpHippo: Help your Hippocampus

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles. [§ 1]

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TCACycle_WP78Go to articleGo to articleGo to articleGo to articleGo to HMDBGo to articleGo to articleGo to articleGo to HMDBGo to HMDBGo to articleGo to WikiPathwaysGo to articleGo to articleGo to articleGo to WikiPathwaysGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to WikiPathwaysGo to articleGo to articleGo to articleGo to HMDBGo to articleGo to articleGo to articleGo to articleGo to articleGo to WikiPathwaysGo to articleGo to WikiPathwaysGo to HMDBGo to articleGo to WikiPathwaysGo to articleGo to HMDBGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to article
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TCACycle_WP78Go to articleGo to articleGo to articleGo to articleGo to HMDBGo to articleGo to articleGo to articleGo to HMDBGo to HMDBGo to articleGo to WikiPathwaysGo to articleGo to articleGo to articleGo to WikiPathwaysGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to WikiPathwaysGo to articleGo to articleGo to articleGo to HMDBGo to articleGo to articleGo to articleGo to articleGo to articleGo to WikiPathwaysGo to articleGo to WikiPathwaysGo to HMDBGo to articleGo to WikiPathwaysGo to articleGo to HMDBGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to articleGo to article
|alt=TCACycle_WP78 edit]]
TCACycle_WP78 edit
  1. ^ The interactive pathway map can be edited at WikiPathways: "TCACycle_WP78".

See also

References

  1. ^ a b Kamzolova, Svetlana V.; Morgunov, Igor G. (2019-12-01). "Microbial production of (2R,3S)-isocitric acid: state of the arts and prospects". Applied Microbiology and Biotechnology. 103 (23): 9321–9333. doi:10.1007/s00253-019-10207-4. ISSN 1432-0614. PMID 31748825.
  2. ^ Saavedra, L.; Garcia, A.; Barbas, C. (9 June 2000). "Development and validation of a capillary electrophoresis method for direct measurement of isocitric, citric, tartaric and malic acids as adulteration markers in orange juice". Journal of Chromatography A. 881 (1–2): 395–401. doi:10.1016/s0021-9673(00)00258-2. PMID 10905722.
  3. ^ a b c Yuzbasheva, Evgeniya Y.; Scarcia, Pasquale; Yuzbashev, Tigran V.; Messina, Eugenia; Kosikhina, Iuliia M.; Palmieri, Luigi; Shutov, Artem V.; Taratynova, Maria O.; Amaro, Rodrigo Ledesma; Palmieri, Ferdinando; Sineoky, Sergey P. (2021-05-01). "Engineering Yarrowia lipolytica for the selective and high-level production of isocitric acid through manipulation of mitochondrial dicarboxylate–tricarboxylate carriers". Metabolic Engineering. 65: 156–166. doi:10.1016/j.ymben.2020.11.001. ISSN 1096-7176. PMID 33161142. S2CID 226286865.
This page was last edited on 26 March 2024, at 18:43
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