Total synthesis of geodiamolide A, a novel cyclodepsipeptide of marine origin

White, James D.; Amedio, John C.

doi:10.1021/jo00265a003

Cited by 95 publications

(47 citation statements)

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“…It is implied that DMAP.TFA in the former example raises the effective concentration of protons thus catalysing macrolactonization. These conditions were also able to catalyse the macrolactonization to form geodiamolide A and B at point (b) in (23) [161,162].…”

Section: Cyclodepsipeptidesmentioning

confidence: 98%

The cyclization of peptides and depsipeptides

Davies

2003

Journal of Peptide Science

417

241

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Constricting the peptide backbone into a more defined conformational form through cyclization is an activity evolved in nature and in synthetic work, the latter straddling only the most recent decades. The resulting conformational constraints increase the probability of an optimum response with bio-receptors. The purpose of this review is to highlight developments that have proved to be reasonably efficient in the macrocyclization of linear precursors into cyclic peptides and depsipeptides.

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Section: Cyclodepsipeptidesmentioning

confidence: 98%

The cyclization of peptides and depsipeptides

Davies

2003

Journal of Peptide Science

417

241

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“…Geodiamolides A and B were examined for antimicrobial activity and were found to be inactive against both Gram-positive and Gram-negative bacteria but active against the yeast Candida albicans [29]. Further evaluation of the compounds at the time of these publications was hindered by lack of pure material, but this need may be partially met by the reported total syntheses of geodiamolides A and B [34,35]. Neosiphoniamolide A did not exhibit anticancer activity, but it did show IC 50 values of < 5 ppm for the inhibition of the growth of the fungi Piricularia oryzae and Helminthosporium gramineum and lower activities against other fungi.…”

Section: Onchidinsmentioning

confidence: 99%

Recent Developments in Depsipeptide Research

Ballard¹,

Yu²,

Wang³

2002

CMC

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This review focuses on the major developments in depsipeptide research since 1995. Depsipeptides are bio-oligomers composed of hydroxy and amino acids linked by amide and ester bonds. Many depsipeptides show very promising biological activities, including anticancer, antibacterial, antiviral, antifungal, anti-inflammatory, and anti-clotting or anti-antherogenic properties. In this report depsipeptides exhibiting these properties are discussed. Their isolation, structural determination, and notable structural features are discussed, but their biological properties and therapeutic potentials are emphasized. Depsipeptides have shown the greatest therapeutic potential as anticancer agents. Four depsipeptides have entered clinical trials for cancer treatment. Among the antiviral compounds discovered, the callipeltins and the quinoxapeptins are particularly promising due to their inhibitory activities against HIV. These compounds have the potential to be developed as anti-AIDS drugs or to serve as lead compounds for the discovery of structurally related anti-AIDS compounds. Antifungal compounds, such as the jaspamides, may lead to therapies against many of the opportunistic infections that accompany AIDS. Anti-inflammatory compounds such as SCH217048 act as neurokinin antagonists and may lead to anti-inflammatory treatments. Some depsipeptides such as micropeptins and A90720A have been found to be effective plasmin inhibitors, which have implications as treatments for cardiovascular diseases. Compounds such as SCH58149 help control the levels of HDL and LDL.

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“…To circumvent this lack of reactivity, the use of malonates or sulfur-containing dianions 204 has proven to be efficient (Scheme 44). By contrast, lithium enolates derived from tertiary amides do react with oxiranes 193,213,214 .…”

Section: Lithium Enolates and Related Compoundsmentioning

confidence: 99%