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the process of removing a carboxyl group from a chemical compound (usually replacing it with hydrogen)

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/09/06 04:02:55」(JST)

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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]

Carboxylation in biochemistry

Carboxyglutamic acid

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.^[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

^ 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.
^ 1-ADAMANTANECARBOXYLIC ACID H. Koch and W. Haaf Organic Syntheses, Coll. Vol. 5, p.20 (1973); Vol. 44, p.1 (1964) Link.
^ 1-METHYLCYCLOHEXANECARBOXYLIC ACID W. Haaf Organic Syntheses, Coll. Vol. 5, p.739 (1973); Vol. 46, p.72 (1966).
^ OMIM - gamma-glutamyl carboxylase, contributed by McKusick VA, last updated October 2004 [1]
^ 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.
^ 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 433109. PMID 1060074.
^ Berg JM, Tymoczko JL, Stryer L. Biochemistry, 5th ed. New York: W. H. Freeman and Company, 2002.

UpToDate Contents

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1. ビタミンＫとγカルボキシグルタミン酸の合成および機能 vitamin k and the synthesis and function of gamma carboxyglutamic acid
2. ビタミンKの概要 overview of vitamin k
3. INRコントロールに対するワルファリンとモジュレーターの生物学 biology of warfarin and modulators of inr control
4. 第VIII因子および第IX因子の生物学と正常な機能 biology and normal function of factor viii and factor ix
5. プロトロンビン遺伝子突然変異：血栓症リスクおよび診断 prothrombin gene mutation thrombotic risk and diagnosis

English Journal

Brain energy metabolism measured by (13) C magnetic resonance spectroscopy in vivo upon infusion of [3-(13) C]lactate.

Duarte JM1, Girault FM1, Gruetter R1,2,3.
Journal of neuroscience research.J Neurosci Res.2015 Jul;93(7):1009-18. doi: 10.1002/jnr.23531. Epub 2014 Dec 17.
The brain uses lactate produced by glycolysis as an energy source. How lactate originated from the blood stream is used to fuel brain metabolism is not clear. The current study measures brain metabolic fluxes and estimates the amount of pyruvate that becomes labeled in glial and neuronal compartment
PMID 25522255

Quantifying vitamin K-dependent holoprotein compaction caused by differential γ-carboxylation using high-pressure size exclusion chromatography.

Vanderslice NC1, Messer AS2, Vadivel K3, Bajaj SP3, Phillips M4, Fatemi M1, Xu W1, Velander WH5.
Analytical biochemistry.Anal Biochem.2015 Jun 15;479:6-14. doi: 10.1016/j.ab.2015.03.019. Epub 2015 Mar 22.
This study uses high-pressure size exclusion chromatography (HPSEC) to quantify divalent metal ion (X(2+))-induced compaction found in vitamin K-dependent (VKD) proteins. Multiple X(2+) binding sites formed by the presence of up to 12 γ-carboxyglutamic acid (Gla) residues are present in plasma-deri
PMID 25804408

C/EBPβ (CEBPB) protein binding to the C/EBP|CRE DNA 8-mer TTGC|GTCA is inhibited by 5hmC and enhanced by 5mC, 5fC, and 5caC in the CG dinucleotide.

Khund Sayeed S1, Zhao J1, Sathyanarayana BK2, Golla JP1, Vinson C3.
Biochimica et biophysica acta.Biochim Biophys Acta.2015 Jun;1849(6):583-9. doi: 10.1016/j.bbagrm.2015.03.002. Epub 2015 Mar 13.
During mammalian development, some methylated cytosines (5mC) in CG dinucleotides are iteratively oxidized by TET dioxygenases to 5-hydroxymethylcytosine (5hmC), 5-formylcytosine (5fC), and 5-carboxylcytosine (5caC). The effect of these cytosine oxidative products on the sequence-specific DNA bindin
PMID 25779641

Japanese Journal

Photosynthesis and nitrogen allocation in needles in the sun and shade crowns of hybrid larch saplings: effect of nitrogen application

Mao Q. Z.,Watanabe M.,Imori M.,Kim Y. S.,Kita K.,Koike T.
Photosynthetica 50(3), 422-428, 2012-09
… The light-saturated net photosynthetic rate (P_[Nmax]) was not significantly affected by N application or crown position, although the contents of N, P, K, and chlorophyll (Chl), and the maximum rates of carboxylation and electron transport were lower in needles of the shade crown than of the sun crown. …
NAID 120004689040

Enzymological Evidence for the Function of a Plastid-Located Pyruvate Carboxylase in the Haptophyte alga Emiliania huxleyi : A Novel Pathway for the Production of C Compounds