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Carboxyglutamic acid information


Carboxyglutamic acid
Names
Systematic IUPAC name
3-Aminopropane-1,1,3-tricarboxylic acid
Other names
γ-Carboxyglutamate
Identifiers
CAS Number
  • 53861-57-7 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 37241
ECHA InfoCard 100.054.607 Edit this at Wikidata
PubChem CID
  • 40772
UNII
  • 16FQV4RZKL checkY
InChI
  • InChI=1/C6H9NO6/c7-3(6(12)13)1-2(4(8)9)5(10)11/h2-3H,1,7H2,(H,8,9)(H,10,11)(H,12,13)
    Key: UHBYWPGGCSDKFX-UHFFFAOYAH
SMILES
  • O=C(O)C(C(=O)O)CC(N)C(=O)O
Properties
Chemical formula
C6H9NO6
Molar mass 191.14 g/mol
Density 1.649 g/mL
Boiling point 418 °C (784 °F; 691 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Carboxyglutamic acid (or the conjugate base, carboxyglutamate), is an uncommon amino acid introduced into proteins by a post-translational carboxylation of glutamic acid residues. This modification is found, for example, in clotting factors and other proteins of the coagulation cascade. This modification introduces an affinity for calcium ions. In the blood coagulation cascade, vitamin K is required to introduce γ-carboxylation of clotting factors II, VII, IX, X and protein Z.[1]

  1. ^ J Stenflo, and J W Suttie (1977). "Vitamin K–dependent formation of γ-carboxyglutamic acid". Annual Review of Biochemistry. 46: 157–172. doi:10.1146/annurev.bi.46.070177.001105. PMID 332061.

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Carboxyglutamic acid

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Carboxyglutamic acid (or the conjugate base, carboxyglutamate), is an uncommon amino acid introduced into proteins by a post-translational carboxylation...

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Osteocalcin

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Osteocalcin, also known as bone gamma-carboxyglutamic acid-containing protein (BGLAP), is a small (49-amino-acid) noncollagenous protein hormone found...

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Gla domain

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Vitamin K-dependent carboxylation/gamma-carboxyglutamic (GLA) domain is a protein domain that contains post-translational modifications of many glutamate...

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Thrombin

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K-dependent reaction that converts 10-12 glutamic acids in the N terminus of the molecule to gamma-carboxyglutamic acid (Gla). In the presence of calcium, the Gla...

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Vitamin K antagonist

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(July 1980). "Mechanism Of Action Of Vitamin K: Synthesis Of Y-Carboxyglutamic Acid". Critical Reviews in Biochemistry. 8 (2): 191–223. doi:10.3109/10409238009105469...

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Carboxylation

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Carboxylation is a chemical reaction in which a carboxylic acid is produced by treating a substrate with carbon dioxide. The opposite reaction is decarboxylation...

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Vitamin K

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Furie BC (March 1999). "Vitamin K–dependent biosynthesis of gamma-carboxyglutamic acid". Blood. 93 (6): 1798–808. doi:10.1182/blood.V93.6.1798.406k22_1798_1808...

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Blood plasma

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anticoagulants like EDTA and citrate salts work by binding calcium (see carboxyglutamic acid), but they may also bind other ions. Even if such ions are not the...

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Factor IX

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Baleja JD (Sep 1995). "Structure of the calcium ion-bound gamma-carboxyglutamic acid-rich domain of factor IX". Biochemistry. 34 (38): 12126–37. doi:10...

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C6H9NO6

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(molar mass: 191.14 g/mol) may refer to: Carboxyglutamic acid Isosorbide mononitrate Nitrilotriacetic acid This set index page lists chemical structure...

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Protein C

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Esmon CT (May 1983). "Proteolytic formation and properties of gamma-carboxyglutamic acid-domainless protein C". The Journal of Biological Chemistry. 258 (9):...

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Prothrombinase

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heavy chain (306 residues). The light chain contains an N-terminal γ-carboxyglutamic acid domain (Gla domain) and two epidermal growth factor-like domains...

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1978 in science

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"Timed appearance of a calcium-binding protein containing gamma-carboxyglutamic acid in developing chick bone". Developmental Biology. 65 (2): 426–34...

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Contryphan

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gamma-carboxyglutamic acid, NH2 = C-terminal amidation and the remainder of the letters refer to the standard one letter abbreviations for amino acids. The...

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GAS6

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43% amino acid identity. It was originally found as a gene upregulated by growth arrested fibroblasts. Gas6 is a gamma-carboxyglutamic acid (Gla) domain-containing...

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Vitamin K reaction

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especially in the bone by carboxylating an amino acid glutamic acid (Glu) to gamma carboxyglutamic acid (Gla). There are controversial results in many studies...

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Johan Stenflo

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RD, Hill RL (May 2009). "The Finding That Prothrombin Contains γ-Carboxyglutamic Acid: the Work of Johan Stenflo". Journal of Biological Chemistry. 284...

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Conantokin

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Pedersen LG, Furie BC, Furie B (December 1997). "Role of gamma-carboxyglutamic acid in the calcium-induced structural transition of conantokin G, a conotoxin...

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Chlorophacinone

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Furie, Barbara C. (1999). "Vitamin K-Dependent Biosynthesis of γ-Carboxyglutamic Acid". Blood. 93 (6): 1798–1808. doi:10.1182/blood.v93.6.1798.406k22_1798_1808...

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