Synthesis of an analogue of mycobactin

Carpenter, Jaswant; Moore, J. W.

doi:10.1039/j39690001610

Cited by 8 publications

(9 citation statements)

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“…It proved difficult to make compounds sufficiently close in structure to the mycobactins to give hope of antagonistic action. The closest structural analogue yet synthesized is a relative of mycobactin T lacking the characteristic iron-chelating groups (22); this compound did not affect the growth of M. tuberculosis. Some growth antagonism effects have been obtained with chromic mycobactin P and with mixtures of mycobactins, though these have no practical therapeutic value.…”

Section: Discovery and Early Historymentioning

confidence: 99%

Mycobactins: iron-chelating growth factors from mycobacteria.

Snow¹

1970

Bacteriological Reviews

216

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Section: Discovery and Early Historymentioning

confidence: 99%

Mycobactins: iron-chelating growth factors from mycobacteria.

Snow¹

1970

Bacteriological Reviews

216

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“…The first example was an analog of mycobactin T lacking the hydroxamic acid and phenolic functionalities needed for iron chelation. 60 The analog demonstrated no appreciable inhibition against M. tuberculosis H37Rv.…”

Section: Mycobactins and Mycobactin Analogs As Anti-mycobacterial Age...mentioning

confidence: 98%

“…Different preparations of cobactin, the second major fragment of mycobactin, are described in this section. Carpenter and Moore initiated studies with synthesis of 69, 60 Subsequently, Hu and Miller, utilized a modified route in which amine 71 was coupled with (R)-3-hydroxybutyric acid (73) in the presence of DCC, DMAP, DMAP•HCl to provide O-TBDPS (tert-butyldiphenylsilyl) protected cobactin T, 75, in 63% yield. 47 For the synthesis of mycobactin analogs with synthetic variation of the normal b-hydroxybutyrate component, 59 four different cobactin derivatives were targeted.…”

Section: Synthesis Of Cobactin 3 and Analogsmentioning

confidence: 99%

“…The route chosen by Carpenter and Moore for the synthesis of the non-chelating analog of mycobactin actually differs from the usual coupling between a mycobactic acid and a cobactin fragment. 60 Indeed, they realized the coupling of fragments 56 and 69 by an ester bond in the presence of the coupling agent carbonyl diimidazole (CDI), and then attached the lipophilic C 18 side-chain (Scheme 23). This route afforded desired mycobactin analog 84.…”

Section: Synthesis Of Mycobactin 1 and Analogsmentioning

confidence: 99%

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Iron chelators from mycobacteria (1954–1999) and potential therapeutic applications

Vergne¹,

Walz²,

Miller³

2000

Nat. Prod. Rep.

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“…The synthesis of an analog missing the iron binding groups was reported in 1969 (Carpenter and Moore 1969). No activity was reported.…”

Section: Limiting Microbial Iron Uptake: Towards the Development Of Nmentioning

confidence: 99%

Utilization of microbial iron assimilation processes for the development of new antibiotics and inspiration for the design of new anticancer agents

et al. 2009

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Pathogenic microbes rapidly develop resistance to antibiotics. To keep ahead in the “microbial war”, extensive interdisciplinary research is needed. A primary cause of drug resistance is the overuse of antibiotics that can result in alteration of microbial permeability, alteration of drug target binding sites, induction of enzymes that destroy antibiotics (ie., beta-lactamase) and even induction of efflux mechanisms. A combination of chemical syntheses, microbiological and biochemical studies demonstrate that the known critical dependence of iron assimilation by microbes for growth and virulence can be exploited for the development of new approaches to antibiotic therapy. Iron recognition and active transport relies on the biosyntheses and use of microbe-selective iron-chelating compounds called siderophores. Our studies, and those of others, demonstrate that siderophores and analogs can be used for iron transport-mediated drug delivery (“Trojan Horse” antibiotics) and induction of iron limitation/starvation (Development of new agents to block iron assimilation). Recent extensions of the use of siderophores for the development of novel potent and selective anticancer agents are also described.

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Synthesis of an analogue of mycobactin

Cited by 8 publications

References 0 publications

Mycobactins: iron-chelating growth factors from mycobacteria.

Mycobactins: iron-chelating growth factors from mycobacteria.

Iron chelators from mycobacteria (1954–1999) and potential therapeutic applications

Utilization of microbial iron assimilation processes for the development of new antibiotics and inspiration for the design of new anticancer agents

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