Β-pirazol-1-il alanina Índice Biosíntesis Síntesis Actividad biológica Referencias Menú de navegaciónNúmero CAS

Aminoácidos


cucurbitáceasácido 2,4-diaminobutíricopirazolidinapirazolserinaadición de Michael














 

L-β-Pirazol-1-ilalanina

L-β-Pyrazol-1-ylalanine.png
Nombre IUPAC

Ácido 2-amino-3-(1-pirazolil)propanoico
General
Fórmula molecular
C6H9N3O2
Identificadores
Número CAS
2734-48-7[1]​
Propiedades físicas
Masa molar
155.156 g/mol
Punto de descomposición
243 ℃ (516 K)
Valores en el SI y en condiciones estándar
(25 ℃ y 1 atm), salvo que se indique lo contrario.
[editar datos en Wikidata]

La L-β-Pirazol-1-ilalanina es una aminoácido no proteínico aislado de las semillas de la sandía (Citrullus vulgaris) y otras plantas cucurbitáceas. [α]20D = -73 (c, 3.4 en agua).[2]​




Índice





  • 1 Biosíntesis


  • 2 Síntesis


  • 3 Actividad biológica


  • 4 Referencias




Biosíntesis


La L-β-Pirazol-1-ilalanina es biosintetizada a partir del 1,3-diaminopropano (producto de descarboxilación del ácido 2,4-diaminobutírico). Esta amina forma el anillo de pirazolidina por heterociclización oxidativa de los extremos de nitrógeno. Seguido de esto, el compuesto sufre de oxidación para formar el anillo de pirazol, el cual se conjuga con una molécula de acetilserina[3]​


BIOSINTESIS DE B-PIRAZOL-1-IL-ALANINA.png


Síntesis


Ferreira y colaboradores establecieron una síntesis de β-Pirazol-1-ilalanina por adición de Michael del pirazol sobre el 2-[bis(ter-butoxicarbonil)amino]prop-2-enoato de metilo.[4]​


Síntesis de β-Pirazol-1-ilalanina.png


Actividad biológica


La β-(pirazol-1-il)-alanina presenta actividad hipoglicémica[5]​



Referencias



  1. ↑ Número CAS


  2. ↑ Dunnill, P.M. et al., Phytochemistry, 1965, 4, 933


  3. ↑ Frisch, D.M. et al., Phytochemistry, 1967, 6, 921


  4. ↑ Ferreira PMT, Maia HLS, Monteiro LS, Tetrahedron Lett., 1998;39:9575.


  5. ↑ Dunnill PM, Fowde L, Phytochemistry, 1965;4:935







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