Leucina

 
Leucina
Estructura químicaModelo tridimensional
Nombre IUPAC
Ácido 2-amino-4-metilpentanoico
General
Símbolo químico Leu, L
Fórmula estructural Imagen de la estructura
Fórmula molecular C6H13NO2
Identificadores
Número CAS 61-90-5[1]​
ChEBI 57427 15603, 57427
ChEMBL CHEMBL291962
ChemSpider 5880
DrugBank DB00149
PubChem 6106
UNII GMW67QNF9C
KEGG C00123 D00030, C00123
CC(C)C[C@H](N)C(O)=O
InChI=InChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t5-/m0/s1
Key: ROHFNLRQFUQHCH-YFKPBYRVSA-N
Propiedades físicas
Densidad 1165 kg/m³; 1,165 g/cm³
Masa molar 13 117 g/mol
Punto de fusión 566 K (293 °C)
Propiedades químicas
Acidez 2,32; 9,58 pKa
Familia Aminoácido
Esencial Sí
Codón UUA, UUG, CUU, CUC, CUA, CUG
Punto isoeléctrico (pH) 5,98
Valores en el SI y en condiciones estándar
(25 ℃ y 1 atm), salvo que se indique lo contrario.
[editar datos en Wikidata]

La leucina (abreviada Leu o L)[2]​ es uno de los veinte aminoácidos que utilizan las células para sintetizar proteínas. Está codificada en el ARN mensajero como UUA, UUG, CUU, CUC, CUA o CUG. Su cadena lateral es no polar, un grupo isobutilo (2-metilpropilo). Es uno de los aminoácidos esenciales. Como un suplemento en la dieta, se ha descubierto que la leucina reduce la degradación del tejido muscular incrementando la síntesis de proteínas musculares en ratas viejas.[3]​ La leucina se usa en el hígado, tejido adiposo, y tejido muscular. En tejido adiposo y muscular, se usa para la formación de esteroles, y solo el uso en estos dos tejidos es cerca de siete veces mayor que el uso en el hígado.[4]​

Propiedades

  • Fórmula: C6H13NO2
  • Denominación de la IUPAC: Leucine
  • Masa molar: 131,17 g/mol

Historia

En 1819, el farmacéutico y químico francés Joseph Louis Proust , logró aislar dos sustancias a base de harina de trigo, que denominó como «ácido caséico» y «óxido caseoso».[5]​ Un año más tarde, Henri Braconnot aisló una nueva sustancia, aparentemente por hidrólisis ácida de la fibra muscular y de la lana y la llamó por el color blanco de los cristales «Leuicin».[6]​ Eduard Mulder reconoció en 1839 la identidad de los dos cuerpos y discutió su posible composición.[7]​ Pero hasta 1891 no lograron el químico alemán Ernst Schulze y su doctorando Arthur Likiernik la constitución de la L-leucina adecuadamente.[8]​

Véase también

Enlaces externos

Referencias

  1. ↑ Número CAS
  2. ↑ IUPAC-IUBMB Joint Commission on Biochemical Nomenclature. "Nomenclature and Symbolism for Amino Acids and Peptides". Recommendations on Organic & Biochemical Nomenclature, Symbols & Terminology etc. Retrieved 2007-05-17.
  3. ↑ L. Combaret, et al. Human Nutrition Research Centre of Clermont-Ferrand. A leucine-supplemented diet restores the defective postprandial inhibition of proteasome-dependent proteolysis in aged rat skeletal muscle]". Journal of Physiology Volume 569, issue 2, p. 489-499. Retrieved 2008-03-25.
  4. ↑ J. Rosenthal, et al. Department of Medicine, University of Toronto, Toronto, Canada. "Metabolic fate of leucine: A significant sterol precursor in adipose tissue and muscle Archivado el 21 de noviembre de 2008 en Wayback Machine.". American Journal of Physiology Vol. 226, No. 2, p. 411-418. Retrieved 2008-03-25.
  5. ↑ L. J. Proust, Sur le Principe qui assaisonne les Fromages., Ann Chim Phys, Band 10, S. 29ff (1819)
  6. ↑ H: Braconnot, Memoire sur un Principe particulier aux graines de la famillie des légumineuses, et analyse des pois et des haricots., Ann Chim Phys, Band 34, S. 68ff (1820)
  7. ↑ S. Hansen: Die Entdeckung der proteinogenen Aminosäuren von 1805 in Paris bis 1935 in Illinois. Archivado el 15 de junio de 2016 en Wayback Machine. Berlin 2015.
  8. ↑ E. Schulze, A. Likernik, Über die Constitution des Leucins, Ber Deutschen Chem Ges, Band 24, S. 669ff (1891)

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