Beilstein J. Org. Chem.2017,13, 2408–2415, doi:10.3762/bjoc.13.238
teicoplanin-related antibacterial A47934 [11], the engineered trisubstituted sulfoteicoplanin aglycone G [12], the echinocandin-like FR901379 [13]; and the sulfated carbapenem MM4550 [14]. A specific amidinohydrolase has been found encoded in the respective biosynthetic gene clusters for the marginolactone
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Scheme 1:
The structures of clethramycin, mediomycins and related linear polyenes.
Beilstein J. Org. Chem.2016,12, 2164–2172, doi:10.3762/bjoc.12.206
on a bacterial artificial chromosome and transplanted into the heterologous host strain Streptomyces lividans, which does not possess the genes for marginolactone production. When furnished with 4-guanidinobutyramide, a specific precursor of the azalomycin starter unit, the recombinant S. lividans
; marginolactone; natural products; polyketide synthase; Introduction
Bacterial modular Type I polyketide synthases (PKSs) are multienzymes that govern the biosynthesis of diverse complex polyketide natural products, including clinically useful antibiotics, immunosuppressants, and antitumor compounds. They follow
predicted to be different (vide infra). We report here that resequencing of the ebelactone modular PKS reveals, surprisingly, that it is fully colinear with no need to invoke iteration. In contrast, the marginolactone PKSs do appear to employ iteration of a single module within the assembly-line.
Results
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Graphical Abstract
Figure 1:
The structures of marginolactones azalomycin and kanchanamycin, and of the β-lactones ebelactone A ...