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Synthesis and characterization of cyclic peptides that are ß-helical in trifluoroethanol.
Fears, Kenan P; Photiadis, Sara J; Kulp, John L; Clark, Thomas D.
Afiliação
  • Fears KP; Division of Chemistry, Naval Research Laboratory, Washington, DC, 20375-5342, USA.
J Pept Sci ; 20(5): 366-74, 2014 May.
Article em En | MEDLINE | ID: mdl-24648029
We show that three designed cyclic d,l-peptides are ß-helical in TFE-a solvent in which the archetypal ß-helical peptide, gA, is unstructured. This result represents an advance in the field of ß-helical peptide foldamers and a step toward achieving ß-helical structure under a broad range of solvent conditions. We synthesized two of the three peptides examined using an improved variant of our original CBC strategy. Here, we began with a commercially available PEG-PS composite resin prefunctionalized with the alkanesulfonamide 'SCL' linker and preloaded with glycine. Our new conditions avoided C-terminal epimerization during the CBC step and simplified purification. In addition, we present results to define the scope and limitations of our CBC strategy. These methods and observations will prove useful in designing additional cyclic ß-helical peptides for applications ranging from transmembrane ion channels to ligands for macromolecular targets. Published 2014. This article is a U.S. Government work and is in the public domain in the USA.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Peptídeos Cíclicos / Trifluoretanol Idioma: En Revista: J Pept Sci Assunto da revista: BIOQUIMICA Ano de publicação: 2014 Tipo de documento: Article País de afiliação: Estados Unidos

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Peptídeos Cíclicos / Trifluoretanol Idioma: En Revista: J Pept Sci Assunto da revista: BIOQUIMICA Ano de publicação: 2014 Tipo de documento: Article País de afiliação: Estados Unidos