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Synthetic strategies to access staphylococcus auto-inducing peptides as quorum sensing modulators.
Gordon, Christopher P.
Afiliação
  • Gordon CP; School of Science and Health, Western Sydney University, Locked Bag 1797, Penrith South DC, NSW 2751, Australia. c.gordon@westernsydney.edu.au.
Org Biomol Chem ; 18(3): 379-390, 2020 01 22.
Article em En | MEDLINE | ID: mdl-31844862
ABSTRACT
The accessory gene regulator (agr) quorum-sensing system is arguably the most important regulator of staphylococcus virulence and has been the focus of tremendous interest in the development of effective therapies for pathogenic bacterial infections. With regards to chemotherapeutic based strategies, the significant proportion of currently reported agr-system modulating molecules are mimics of the native ArgC substrate, which is a thioester-based macrocyclic peptide know as the auto-inducing peptide. Over the past two decades, more than two-hundred synthetic analogues have been reported. This review traces the development of the synthetic strategies employed to synthesise these analogues with a particular focus on macrocyclisation. At present these synthetic approaches can be clustered into five broad categories (1) solution-phase cyclisation, (2) immobilised carbodiimide assisted cyclisation, (3) concomitant on-resin cleavage and macrocyclisation, (4) Boc-compatible chemoselective thioesterification, and (5) Fmoc-compatible chemoselective thioesterification. The advantages and limitation provided by each of the approaches are compared and contrasted with a view towards potential reaction scale-up.
Assuntos

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Peptídeos Cíclicos / Staphylococcus / Percepção de Quorum / Peptidomiméticos / Antibacterianos Idioma: En Ano de publicação: 2020 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Peptídeos Cíclicos / Staphylococcus / Percepção de Quorum / Peptidomiméticos / Antibacterianos Idioma: En Ano de publicação: 2020 Tipo de documento: Article