Structurally Selective Assembly of a Specific Macrobicycle From a Dynamic Library of Pseudopeptidic Disulfides

Molecular recognition is essential in many chemical and biological processes. Studying the behavior of pseudopeptides using dynamic covalent chemistry allows the exploration of a wide range of structural components and molecular interactions with minimal synthetic effort. Herein, we describe how non...

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Detalles Bibliográficos
Autores: Lafuente, Maria, Alfonso, Ignacio, Solà Oller, Jordi
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2019
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/179334
Acceso en línea:http://hdl.handle.net/10261/179334
Access Level:acceso abierto
Palabra clave:Topology
Peptidomimetics
Self-assembly
Noncovalent interactions
Descripción
Sumario:Molecular recognition is essential in many chemical and biological processes. Studying the behavior of pseudopeptides using dynamic covalent chemistry allows the exploration of a wide range of structural components and molecular interactions with minimal synthetic effort. Herein, we describe how non‐covalent attractive forces in pseudopeptidic building blocks can successfully guide the product distribution in a dynamic library towards topologically more complex compounds that are in principle not expected. The interactions described herein are highly dependent on molecular architecture and media so effective recognition can be altered by just minimal structural or environmental changes. Thus, the chemical and constitutional information contained in the respective building blocks is decoded and expressed through dynamic covalent and non‐covalent bonds in the assembly of either a single macrostructure or an ensemble of components with larger structural diversity. The understanding of supramolecular forces responsible for the component assembly in minimalistic systems can help to comprehend more complex bio‐related processes such as protein folding or protein−protein interactions.