Α-hydroxyisobutyric_acid

2-Hydroxyisobutyric acid

2-Hydroxyisobutyric acid

Chemical compound

2-Hydroxyisobutyric acid is the organic compound with the formula (CH3)2C(OH)CO2H. A white solid, it is classified as an hydroxycarboxylic acid. It has been considered as a naturally occurring precursor to polyesters.[3] It is closely related to lactic acid (CH3CH(OH)CO2H).[4]

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Occurrences

The enzyme 2-hydroxyisobutyryl coenzyme A (CoA) mutase isomerizes 3-hydroxybutyryl coenzyme A into 2-hydroxyisobutyryl coenzyme A. Hydrolysis of the latter gives 2-hydroxyisobutyric acid.[5]

The amides formed from this carboxylic acid and the ε-amino group of lysine residues are a kind of post translational modification.[6][7]

Ethyl methacrylate (an industrially important monomer and ester of methacrylic acid) was first obtained by treating the ethyl ester of 2-hydroxyisobutyric acid with phosphorus pentachloride in an apparent dehydration reaction.[8]

See also

References

  1. [1]
    W.P.J.Gaykema; J.A.Kanters; G.Roelofsen (1978), Cryst. Struct. Commun., 47: 463
  2. [2]
    "2-Hydroxyisobutyric acid". pubchem.ncbi.nlm.nih.gov.
  3. [3]
    Bhatia, Shashi Kant; Bhatia, Ravi Kant; Yang, Yung-Hun (2016). "Biosynthesis of Polyesters and Polyamide Building Blocks Using Microbial Fermentation and Biotransformation". Reviews in Environmental Science and Bio/Technology. 15 (4): 639–663. doi:10.1007/s11157-016-9415-9. S2CID 88561532.
  4. [4]
    Miltenberger, Karlheinz (2000). "Hydroxycarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_507. ISBN 978-3527306732.
  5. [5]
    Rohde, Maria-Teresa; Tischer, Sylvi; Harms, Hauke; Rohwerder, Thore (2017). "Production of 2-Hydroxyisobutyric Acid from Methanol by Methylobacterium extorquens AM1 Expressing ( R )-3-Hydroxybutyryl Coenzyme A-Isomerizing Enzymes". Applied and Environmental Microbiology. 83 (3). Bibcode:2017ApEnM..83E2622R. doi:10.1128/AEM.02622-16. PMC 5244315. PMID 27836853.
  6. [6]
    Dai, Lunzhi; Peng, Chao; Montellier, Emilie; Lu, Zhike; Chen, Yue; Ishii, Haruhiko; Debernardi, Alexandra; Buchou, Thierry; Rousseaux, Sophie; Jin, Fulai; Sabari, Benjamin R.; Deng, Zhiyou; Allis, C David; Ren, Bing; Khochbin, Saadi; Zhao, Yingming (2014). "Lysine 2-Hydroxyisobutyrylation is a Widely Distributed Active Histone Mark". Nature Chemical Biology. 10 (5): 365–370. doi:10.1038/nchembio.1497. PMID 24681537.
  7. [7]
    Carrola, Joana; Rocha, CláUdia M.; Barros, António S.; Gil, Ana M.; Goodfellow, Brian J.; Carreira, Isabel M.; Bernardo, João; Gomes, Ana; Sousa, Vitor; Carvalho, Lina; Duarte, Iola F. (2011). "Metabolic Signatures of Lung Cancer in Biofluids: NMR-Based Metabonomics of Urine". Journal of Proteome Research. 10 (1): 221–230. doi:10.1021/pr100899x. PMID 21058631.
  8. [8]
    E. Frankland, B. F. Duppa (1865). "Untersuchungen über Säuren aus der Acrylsäure-Reihe; 1) Umwandlung der Säuren aus der Milchsäure-Reihe in die der Acrylsäure-Reihe". Justus Liebigs Annalen der Chemie. 136: 12. doi:10.1002/jlac.18651360102.
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