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Wikipedia

Citramalic acid

Citramalic acid is the organic compound with the formula HO2CCH2C(CH3)(OH)CO2H. A chiral compound, it is related structurally to malic acid.

Citramalic acid
Names
Other names
(R)-2-hydroxy-2-methylbutanedioic acid, 2-methylmalic acid, D-(−)-2-methylmalic acid, (R)-2-hydroxy-2-methylsuccinic acid
Identifiers
  • 6236-10-8 R-enantiomer
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:15586
ChemSpider
  • 388822
ECHA InfoCard 100.154.104
EC Number
  • ±: 209-901-5
KEGG
  • C02612
  • 439766
UNII
  • 788CNO6T4D
  • DTXSID80331440
  • InChI=1S/C5H8O5/c1-5(10,4(8)9)2-3(6)7/h10H,2H2,1H3,(H,6,7)(H,8,9)/t5-/m1/s1
    Key: XFTRTWQBIOMVPK-RXMQYKEDSA-N
  • C[C@@](CC(=O)O)(C(=O)O)O
Properties
C5H8O5
Molar mass 148.114 g·mol−1
Appearance white solid
Hazards
GHS labelling:
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Synthesis and reactions edit

Citramalic acid is the hydrated derivative of mesaconic acid, The hydration is catalyzed by mesaconyl-C4-CoA hydratase:

HO2CCH=C(CH3)CO2H + H2O → HO2CCH2C(CH3)(OH)CO2H

The same conversion can be achieved in vitro.[1]

The enzyme (S)-citramalyl-CoA lyase converts citramalyl-CoA to acetyl-CoA and pyruvate.[2]

References edit

  1. ^ Eck, Richard; Simon, Helmut (1994). "Preparation of Both Enantiomers of Malic and Ctramalic Acid and Other Hydroxysuccinic Acid Derivatives by Stereospecific Hydrations of cis or trans 2-Butene-1,4-dioic Acids with Resting Cells of Clostridium formicoaceticum". Tetrahedron. 50 (48): 13641–13654. doi:10.1016/S0040-4020(01)85678-7.
  2. ^ Berg, Ivan A. (2011). "Ecological Aspects of the Distribution of Different Autotrophic CO2 Fixation Pathways". Applied and Environmental Microbiology. 77 (6): 1925–1936. Bibcode:2011ApEnM..77.1925B. doi:10.1128/AEM.02473-10. PMC 3067309. PMID 21216907.

citramalic, acid, organic, compound, with, formula, ho2cch2c, co2h, chiral, compound, related, structurally, malic, acid, namesother, names, hydroxy, methylbutanedioic, acid, methylmalic, acid, methylmalic, acid, hydroxy, methylsuccinic, acididentifierscas, nu. Citramalic acid is the organic compound with the formula HO2CCH2C CH3 OH CO2H A chiral compound it is related structurally to malic acid Citramalic acid NamesOther names R 2 hydroxy 2 methylbutanedioic acid 2 methylmalic acid D 2 methylmalic acid R 2 hydroxy 2 methylsuccinic acidIdentifiersCAS Number 6236 10 8 R enantiomer3D model JSmol Interactive imageChEBI CHEBI 15586ChemSpider 388822ECHA InfoCard 100 154 104EC Number 209 901 5KEGG C02612PubChem CID 439766UNII 788CNO6T4DCompTox Dashboard EPA DTXSID80331440InChI InChI 1S C5H8O5 c1 5 10 4 8 9 2 3 6 7 h10H 2H2 1H3 H 6 7 H 8 9 t5 m1 s1Key XFTRTWQBIOMVPK RXMQYKEDSA NSMILES C C CC O O C O O OPropertiesChemical formula C 5H 8O 5Molar mass 148 114 g mol 1Appearance white solidHazardsGHS labelling PictogramsSignal word WarningHazard statements H315 H319 H335Precautionary statements P261 P264 P271 P280 P302 P352 P304 P340 P305 P351 P338 P312 P321 P332 P313 P337 P313 P362 P403 P233 P405 P501Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesSynthesis and reactions editCitramalic acid is the hydrated derivative of mesaconic acid The hydration is catalyzed by mesaconyl C4 CoA hydratase HO2CCH C CH3 CO2H H2O HO2CCH2C CH3 OH CO2HThe same conversion can be achieved in vitro 1 The enzyme S citramalyl CoA lyase converts citramalyl CoA to acetyl CoA and pyruvate 2 References edit Eck Richard Simon Helmut 1994 Preparation of Both Enantiomers of Malic and Ctramalic Acid and Other Hydroxysuccinic Acid Derivatives by Stereospecific Hydrations of cis or trans 2 Butene 1 4 dioic Acids with Resting Cells of Clostridium formicoaceticum Tetrahedron 50 48 13641 13654 doi 10 1016 S0040 4020 01 85678 7 Berg Ivan A 2011 Ecological Aspects of the Distribution of Different Autotrophic CO2 Fixation Pathways Applied and Environmental Microbiology 77 6 1925 1936 Bibcode 2011ApEnM 77 1925B doi 10 1128 AEM 02473 10 PMC 3067309 PMID 21216907 Retrieved from https en wikipedia org w index php title Citramalic acid amp oldid 1056091798, wikipedia, wiki, book, books, library,

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