Synthesis and biological evaluation of truncated derivatives of abyssomicin C as antibacterial agents

Monjas, Leticia; Fodran, Peter; Kollback, Johanna; Cassani, Carlo; Olsson, Thomas; Genheden, Maja; Larsson, D. G. Joakim; Wallentin, Carl‐Johan

doi:10.3762/bjoc.15.147

Cited by 3 publications

(2 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The structures in Figure 2 exemplify distinctive marine-derived antibacterials. The abyssomicin family of macrolactones (more than thirty spirotetronate structures, exemplified here by abyssomicin C) is encountered as secondary metabolites of marine Streptomyces [ 49 , 50 , 51 , 52 , 53 , 54 ]. The abyssomicins have attracted extensive synthetic (notably, evaluation of the property of many members of this family, including abyssomicin C, to show room-temperature atropisomers) and biosynthetic studies.…”

Section: Do Marine Organisms Biosynthesize Exceptional Inhibitors Of ...mentioning

confidence: 99%

β-Lactams from the Ocean

Fisher

Mobashery

2023

Marine Drugs

View full text Add to dashboard Cite

The title of this essay is as much a question as it is a statement. The discovery of the β-lactam antibiotics—including penicillins, cephalosporins, and carbapenems—as largely (if not exclusively) secondary metabolites of terrestrial fungi and bacteria, transformed modern medicine. The antibiotic β-lactams inactivate essential enzymes of bacterial cell-wall biosynthesis. Moreover, the ability of the β-lactams to function as enzyme inhibitors is of such great medical value, that inhibitors of the enzymes which degrade hydrolytically the β-lactams, the β-lactamases, have equal value. Given this privileged status for the β-lactam ring, it is therefore a disappointment that the exemplification of this ring in marine secondary metabolites is sparse. It may be that biologically active marine β-lactams are there, and simply have yet to be encountered. In this report, we posit a second explanation: that the value of the β-lactam to secure an ecological advantage in the marine environment might be compromised by its close structural similarity to the β-lactones of quorum sensing. The steric and reactivity similarities between the β-lactams and the β-lactones represent an outside-of-the-box opportunity for correlating new structures and new enzyme targets for the discovery of compelling biological activities.

show abstract

Section: Do Marine Organisms Biosynthesize Exceptional Inhibitors Of ...mentioning

confidence: 99%

β-Lactams from the Ocean

Fisher

Mobashery

2023

Marine Drugs

View full text Add to dashboard Cite

show abstract

“…Monjas et al. synthesized truncated derivatives of abyssomycin C and studied their structure-activity relationship towards ADC synthase and these derivatives were found to have lower antibacterial activity compared to abyssomycin C [56] .…”

Section: Antibacterial Agents Derived From the Mother Naturementioning

confidence: 99%