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Fig. 5.4
Examples of naturally occurring sideromycins. The antibiotic moiety is highlighted in
blue
, the linker in
green
[
61
]
Fig. 5.5
Synthetic sideromycins inspired by the natural occurring Salmycins. The antibiotic
moiety is highlighted in
blue
, the linker in
green
[
48
,
51
,
61
]
and
Salmonella
spp. MccE492 enters the bacteria through the siderophore-uptake
system and disrupts the cytoplasmic membrane while interacting with other intra-
cellular proteins [
43
-
46
].
Salmycin B (
11
, Fig.
5.5
) represents another example of a naturally occurring
sideromycin. Isolated by Vértesy from
Streptomyces violaceous
DSM 8286, this
and other related salmycins (
10
-
13
) are potent growth inhibitors of Staphylococci
and Streptococci [
47
]. The assembly of the hydroxamate-based siderophore por-
tion, danoxamine (Dan), allowed the complete synthesis of desferrisalmycin B
[
48
,
49
]. The availability of synthetic fragments aided the correct stereochemical
assignment of the antibiotic moiety. Wencewicz explored the use of Dan to deliver
different antibiotics (
14
-
16
) in an attempt to mimic the nature-inspired activity of
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