An iterative in silico and modular synthetic approach to aqueous soluble tercyclic α-helix mimetics.
Org Biomol Chem
; 12(25): 4432-44, 2014 Jul 07.
Article
em En
| MEDLINE
| ID: mdl-24847981
ABSTRACT
Tercyclic scaffolds, designed to have improved synthetic accessibility and aqueous solubility, were evaluated as structural α-helix mimetics by using an iterative in silico approach. The synthesis of these tercyclic scaffolds was accomplished using a modular synthetic approach by employing functionalised methoxyphenyl units which were readily manipulated to allow the introduction of various nitrogen-based heterocycles. The ability of these scaffolds to mimic the key i, i + 3 and i + 7 residues of a polyalanine α-helix was ratified by in silico studies, X-ray crystallographic and NOESY analysis, and their aqueous solubility was measured by a kinetic turbidimetric method.
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MEDLINE
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Peptídeos
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Simulação por Computador
Idioma:
En
Revista:
Org Biomol Chem
Assunto da revista:
BIOQUIMICA
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QUIMICA
Ano de publicação:
2014
Tipo de documento:
Article
País de afiliação:
Austrália