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CARBOXYLATION

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

Contents
Carboxylation in organic chemistry
Carboxylation in biochemistry
References

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]

Carboxylation in biochemistry


Carboxylation in biochemistry is a posttranslational modification of glutamate residues 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.[4]
The carboxylase requires vitamin K as a cofactor and performs the reaction in a processive manner.[5] γ-carboxyglutamate binds calcium, which is essential for its activity.[6] 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.[7]

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. OMIM - gamma-glutamyl carboxylase, contributed by McKusick VA, last updated October 2004 [1]
5. Processive post-translational modification. Vitamin K-dependent carboxylation of a peptide substrate, Morris DP, Stevens RD, Wright DJ, Stafford DW, , , J. Biol. Chem., 1995
6. Direct identification of the calcium-binding amino acid, gamma-carboxyglutamate, in mineralized tissue, Hauschka PV, Lian JB, Gallop PM, , , Proc. Natl. Acad. Sci. U.S.A., 1975
7. Berg JM, Tymoczko JL, Stryer L. ''Biochemistry'', 5th ed. New York: W. H. Freeman and Company, 2002.


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