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Karboksilacija

Karboksilacija u hemiji je hemijska reakcija u kojoj se uvodi karboksilna grupa u supstrat. Suprotna reakcija je dekarboksilacija.

Karboksilacija u organskog hemiji

[уреди | уреди извор]

In organskoj hemiji postoji mnoštvo različitih protokola za karboksilaciju. Jedan opšti pristup je reakcija nukleofila sa suvim ledom (čvrstim ugljen-dioksidom)[1] ili mravljom kiselinom[2][3]

Karboksilacija u biohemiji

[уреди | уреди извор]
Karboksiglutaminska kiselina

Karboksilacija u biohemiji je posttranslaciona modifikacija glutamatnih ostataka, do γ-karboksiglutamata, u proteinima. Ona se javlja primarno u proteinima koji učestvuju u kaskadi zgrušavanja krvi, specifično faktorima II, VII, IX, i X, proteinu C, proteinu S, kao i u nekim proteinima kostiju. Ova modifikacija je neophodna da bi ti proteini funkcionisali. Do karboksilacije dolazi u jetri, a vrši je γ-glutamil karboksilaza.[4]

Za rad karboksilaze neophodan je vitamin K kao kofaktor.[5] γ-karboksiglutamat vezuje kalcijum, koji je esencijalan za njegovi dejstvo.[6] Na primer, u protrombinu, vezivanje kalcijuma omogućava proteinu da se veže za ćelijsku membranu u trombocitima, što ga dovodi u blizinu proteina koji odvajaju protrombin, čime se aktivira trombin nakon povrede.[7]

  1. ^ Regio- i 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. ^ 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. PMID 8530480. doi:10.1074/jbc.270.51.30491. 
  6. ^ 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. PMC 433109Слободан приступ. PMID 1060074. doi:10.1073/pnas.72.10.3925. 
  7. ^ Berg JM, Tymoczko JL, Stryer L. Biochemistry, 5th ed. New York: W. H. Freeman and Company, 2002.
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Karboksilacija
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