Pradimicin and Benanomicin Antibiotics: From Antifungal Polyketide Natural Products to Antiviral Agents with a Unique Carbohydrate- Binding Mode of Action

Pp: 31-109 (79)

* (Excluding Mailing and Handling)

Abstract

The family of benanomicin-pradimicin antibiotics (BPAs) is reviewed exhaustively with respect to its structural, functional, mechanistic and synthetic aspects. BPAs can be considered a unique class of compounds from the structural point of view due to the presence of a 5,6-dihydro-benzo[α]naphthacenequinone (DHBNQ) scaffold attached to a glycan moiety. The mechanism of action is ‘lectin-like’ and related to the selective recognition and binding to specific mannoside residues located at the surface of the membrane of fungal and viral pathogens. BPAs are prototype structures of non-peptidic small-size carbohydrate-binding agents (CBAs).

Keywords: 5, 6-dihydro-benzo[α]naphthacenequinone (DHBNQ), Antibiotics, Antifungal, Antiviral, Aromatic Polyketides, Atropisomerism, Benanomicin, Benanomicin-Pradimicin Antibiotics (BPAs), Biosynthesis, Carbohydrate- Binding Agents (CBAs), Natural products, Pradimicin, Total Synthesis.