Carboxylation

Carboxylation in chemistry is a chemical reaction in which a carboxylic acid group is introduced in a substrate. The opposite reaction is decarboxylation.

Carboxylation in organic chemistry

In organic chemistry many different protocols exist for carboxylation. One general approach is by reaction of nucleophiles with dry ice (solid carbon dioxide)[1] or formic acid[2][3] An example is the Kolbe–Schmitt reaction. Carboxylation catalysts are N-Heterocyclic carbenes [4] and catalysts based on silver.[5]

Carboxylation in biochemistry

Carboxyglutamic acid
Further information: Carboxy-lyases

Carboxylation in biochemistry is a posttranslational modification of glutamate residues, to γ-carboxyglutamate, in proteins. It occurs primarily in proteins involved in the blood clotting cascade, specifically factors II, VII, IX, and X, protein C, and protein S, and also in some bone proteins. This modification is required for these proteins to function. Carboxylation occurs in the liver and is performed by γ-glutamyl carboxylase.[6]

The carboxylase requires vitamin K as a cofactor and performs the reaction in a processive manner.[7] γ-carboxyglutamate binds calcium, which is essential for its activity.[8] For example, in prothrombin, calcium binding allows the protein to associate with the plasma membrane in platelets, bringing it into close proximity with the proteins that cleave prothrombin to active thrombin after injury.[9]

References

  1. ↑ REGIO- AND STEREOSELECTIVE CARBOXYLATION OF ALLYLIC BARIUM REAGENTS: (E)-4,8-DIMETHYL-3,7-NONADIENOIC ACID Akira Yanagisawa, Katsutaka Yasue, and Hisashi Yamamoto1 Organic Syntheses, Coll. Vol. 9, p.317 (1998); Vol. 74, p.178 (1997) link.
  2. ↑ 1-ADAMANTANECARBOXYLIC ACID H. Koch and W. Haaf Organic Syntheses, Coll. Vol. 5, p.20 (1973); Vol. 44, p.1 (1964) Link.
  3. ↑ 1-METHYLCYCLOHEXANECARBOXYLIC ACID W. Haaf Organic Syntheses, Coll. Vol. 5, p.739 (1973); Vol. 46, p.72 (1966).
  4. ↑ N-Heterocyclic carbene (NHC)–copper-catalysed transformations of carbon dioxide Liang Zhang and Zhaomin Hou Chem. Sci., 2013,4, 3395-3403 doi:10.1039/C3SC51070K
  5. ↑ Silver-catalyzed carboxylation K. Sekine and T. Yamada Chem. Soc. Rev., 2016, doi:10.1039/C5CS00895F
  6. ↑ OMIM - gamma-glutamyl carboxylase, contributed by McKusick VA, last updated October 2004
  7. ↑ Morris DP, Stevens RD, Wright DJ, Stafford DW (1995). "Processive post-translational modification. Vitamin K-dependent carboxylation of a peptide substrate". J. Biol. Chem. 270 (51): 30491–8. doi:10.1074/jbc.270.51.30491. PMID 8530480.
  8. ↑ Hauschka PV, Lian JB, Gallop PM (1975). "Direct identification of the calcium-binding amino acid, gamma-carboxyglutamate, in mineralized tissue". Proc. Natl. Acad. Sci. U.S.A. 72 (10): 3925–9. doi:10.1073/pnas.72.10.3925. PMC 433109Freely accessible. PMID 1060074.
  9. ↑ Berg JM, Tymoczko JL, Stryer L. Biochemistry, 5th ed. New York: W. H. Freeman and Company, 2002.
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