Abyssomicin C – ein polycyclisches Antibiotikum aus einem marinen Verrucosispora‐Stamm als Inhibitor für die p‐Aminobenzoesäure/Tetrahydrofolat‐Biosynthese

Abstract

Aus der Tiefe: Der Biosyntheseweg von p‐Aminobenzoesäure bietet mehrere Angriffspunkte zur Bekämpfung pathogener Mikroorganismen. Abyssomicin C (siehe Formel) ist ein neues Antibiotikum, das die Biosyntheseschritte zwischen Chorisminsäure und p‐Aminobenzoesäure hemmt. Die antibiotische Aktivität beruht möglicherweise auf einer irreversiblen Enzyminaktivierung, die durch eine Michael‐Addition vermittelt wird.

Analysis of the Tetronomycin Gene Cluster: Insights into the Biosynthesis of a Polyether Tetronate Antibiotic

“…The ring is created by annealing a glyceryl-thioester unit, which is derived from 1,3-bisphosphoglycerate, onto a full-length linear poly-A C H T U N G T R E N N U N G ketide, [19] as previously suggested for spirotetronate biosynthesis. [2,5] In principle, a very similar reaction sequence could also account for the production of the tetronate ring of tetronasin (4). In this case, additional enzyme-catalysed steps that lead to the loss of the side-chain carbon atom from the tetronate moiety would be required.…”

Abyssomicins from the South China Sea Deep‐Sea Sediment Verrucosispora sp.: Natural Thioether Michael Addition Adducts as Antitubercular Prodrugs

“…(MS100128). Bioassay-directed fractionation of a large scale (21 L) culture of MS100128 yielded three new members of the rare class of abyssomicin polyketides, abyssomicins J ( 1 ), K ( 2 ), and L ( 3 ), and the four known2 abyssomicins B ( 4 ), C ( 5 ), D ( 6 ), and H ( 10 ) (Figure 1). All structures were assigned by detailed spectroscopic analysis, with the known abyssomicins 4 – 6 and 10 documented in the Supporting Information, and the new abyssomicins 1 – 3 discussed below.…”

Biomimetic Synthesis of Non‐Aromatic Polycyclic Polyketides

“…Abyssomicin C (54) is an antibiotic isolated in 2004 from the marine actinomycete Verrucosispora AB 18-032 [53]. Sorensen and coworkers suggested in 2005 that the biosynthesis of 54 involves an IMDA reaction [54].…”