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Amino acids are the monomers that comprise proteins. Each amino acid has the same fundamental structure, which consists of a central carbon atom, or the alpha (α) carbon, bonded to an amino group (NH2), a carboxyl group (COOH), and to a hydrogen atom. Every amino acid also has another atom or group of atoms bonded to the central atom known as the R group. There are 20 common amino acids present in proteins, each with a different R group. Variation in the amino acid sequence is responsible for...
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Las cadenas polipeptídicas que contienen D-gamma-hidroxivalina.

Katarzyna Pisarewicz1, David Mora, Fred C Pflueger

  • 1Department of Chemistry & Biochemistry and Center of Excellence in Biomedical & Marine Biotechnology, Florida Atlantic University, 777 Glades Road, Boca Raton, Florida 33431, USA.

Journal of the American Chemical Society
|April 28, 2005
PubMed
Resumen
Este resumen es generado por máquina.

Los investigadores descubrieron ácidos d-amino inusuales, d-Val y d-gamma-hidroxivalina (d-Hyv), en péptidos de veneno de caracol cono. Estos hallazgos desafían la típica l-homociralidad de la vida y sugieren nuevas vías enzimáticas.

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Área de la Ciencia:

  • La bioquímica es la bioquímica.
  • Química del péptido Química del péptido
  • Investigación del veneno Investigación del veneno.

Sus antecedentes:

  • La vida exhibe una distinta l-homociralidad, con las proteínas que utilizan principalmente los ácidos l-amino.
  • El veneno del caracol cono contiene diversos péptidos (conopéptidos) con diversas actividades biológicas.

Objetivo del estudio:

  • Investigar la presencia y las características estructurales de aminoácidos inusuales en conopeptidos recién aislados.
  • Aclarar los nuevos motivos estructurales y los posibles mecanismos enzimáticos involucrados en su síntesis.

Principales métodos:

  • Aislamiento y purificación de cuatro conopéptidos: gld-V/gld-V' y mus-V/mus-V'.
  • Determinación de secuencias completas de aminoácidos utilizando técnicas nano/pico-NMR y MS/MS.
  • Análisis de nuevos motivos estructurales y sus interacciones estabilizadoras.

Principales resultados:

  • Descubrimiento de d-Val y d-gamma-hidroxivalina (d-Hyv) dentro de las cadenas de polipéptidos expresados ribosomalmente.
  • Identificación de un nuevo motivo Ser-d-Hyv-Trp en los gamma-hidroxiconofanos, estabilizado por interacciones específicas.
  • Caracterización de los conofanos atípicos y los gamma-hidroxiconofanos que carecen de restricciones típicas y exhiben una alta hidroxilación.

Conclusiones:

  • La presencia de ácidos d-amino en los conopéptidos desafía los principios fundamentales de la homoquiralidad biológica.
  • Los nuevos motivos estructurales y un posible mecanismo de hiperhidroxilación en el veneno del caracol cono mejoran la orientación neuronal.
  • Los hallazgos sugieren la existencia de una enzima d-esteroespecífica involucrada en la oxidación d-Val.