2-Hydroxyisobutyric acid explained

2-Hydroxyisobutyric acid is the organic compound with the formula . A white solid, it is classified as an hydroxycarboxylic acid. It has been considered as a naturally occurring precursor to polyesters.[1] It is closely related to lactic acid .

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.[2]

The amides formed from this carboxylic acid and the ε-amino group of lysine residues are a kind of post translational modification.[3] [4]

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.[5]

See also

Notes and References

  1. 10.1007/s11157-016-9415-9. Biosynthesis of Polyesters and Polyamide Building Blocks Using Microbial Fermentation and Biotransformation . 2016 . Bhatia . Shashi Kant . Bhatia . Ravi Kant . Yang . Yung-Hun . Reviews in Environmental Science and Bio/Technology . 15 . 4 . 639–663 . 88561532 .
  2. 10.1128/AEM.02622-16. Production of 2-Hydroxyisobutyric Acid from Methanol by Methylobacterium extorquens AM1 Expressing (R)-3-Hydroxybutyryl Coenzyme A-Isomerizing Enzymes . 2017 . Rohde . Maria-Teresa . Tischer . Sylvi . Harms . Hauke . Rohwerder . Thore . Applied and Environmental Microbiology . 83 . 3 . 27836853 . 5244315 . 2017ApEnM..83E2622R .
  3. 10.1038/nchembio.1497. Lysine 2-Hydroxyisobutyrylation is a Widely Distributed Active Histone Mark . 2014 . 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 . Nature Chemical Biology . 10 . 5 . 365–370 . 24681537 .
  4. 10.1021/pr100899x. Metabolic Signatures of Lung Cancer in Biofluids: NMR-Based Metabonomics of Urine . 2011 . 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. . Journal of Proteome Research . 10 . 1 . 221–230 . 21058631 .
  5. Justus Liebigs Annalen der Chemie. 136. 12. Untersuchungen über Säuren aus der Acrylsäure-Reihe; 1) Umwandlung der Säuren aus der Milchsäure-Reihe in die der Acrylsäure-Reihe. E. Frankland, B. F. Duppa. 1865. 10.1002/jlac.18651360102.

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