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Scalable synthesis and coupling of quaternary α-arylated amino acids: α-aryl substituents are tolerated in α-helical peptides.
Leonard, Daniel J; Zieleniewski, Francis; Wellhöfer, Isabelle; Baker, Emily G; Ward, John W; Woolfson, Derek N; Clayden, Jonathan.
Afiliación
  • Leonard DJ; School of Chemistry, University of Bristol Cantock's Close Bristol BS8 1TS UK D.N.Woolfson@bristol.ac.uk j.clayden@bristol.ac.uk.
  • Zieleniewski F; School of Chemistry, University of Bristol Cantock's Close Bristol BS8 1TS UK D.N.Woolfson@bristol.ac.uk j.clayden@bristol.ac.uk.
  • Wellhöfer I; School of Chemistry, University of Bristol Cantock's Close Bristol BS8 1TS UK D.N.Woolfson@bristol.ac.uk j.clayden@bristol.ac.uk.
  • Baker EG; School of Chemistry, University of Bristol Cantock's Close Bristol BS8 1TS UK D.N.Woolfson@bristol.ac.uk j.clayden@bristol.ac.uk.
  • Ward JW; School of Biochemistry, University of Bristol, Medical Sciences Building, University Walk Bristol BS8 1TS UK.
  • Woolfson DN; Bristol BioDesign Institute, University of Bristol, Life Sciences Building Tyndall Avenue Bristol BS8 1TQ UK.
  • Clayden J; School of Chemistry, University of Bristol Cantock's Close Bristol BS8 1TS UK D.N.Woolfson@bristol.ac.uk j.clayden@bristol.ac.uk.
Chem Sci ; 12(27): 9386-9390, 2021 Jul 14.
Article en En | MEDLINE | ID: mdl-34349911
Quaternary amino acids are important tools for the modification and stabilisation of peptide secondary structures. Here we describe a practical and scalable synthesis applicable to quaternary alpha-arylated amino acids (Q4As), and the development of solid-phase synthesis conditions for their incorporation into peptides. Monomeric and dimeric α-helical peptides are synthesised with varying degrees of Q4A substitution and their structures examined using biophysical methods. Both enantiomers of the Q4As are tolerated in folded monomeric and oligomeric α-helical peptides, with the (R)-enantiomer slightly more so than the (S).
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Sci Año: 2021 Tipo del documento: Article Pais de publicación: Reino Unido
Texto completo
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XML
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Sci Año: 2021 Tipo del documento: Article Pais de publicación: Reino Unido