Biosynthesis of the Marine Cyanobacterial Metabolite Barbamide. 1. Origin of the Trichloromethyl Group

Sitachitta, Namthip; Rossi, James V.; Roberts, M. W.; Gerwick, William H.; Fletcher, Matthew D.; Willis, Christine L.

doi:10.1021/ja9811389

Cited by 89 publications

(64 citation statements)

References 6 publications

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“…The origin of the trichloromethyl group in barbamide (70) (Fig. (14)) was shown to be of leucine origin [116]. Further recent examples of cyanobacterial trichloromethyl-containing modified peptides are pseudodysidenin (97) and dysidenamide (98) [113] (Fig.…”

Section: Biosynthetic Signatures In Cyanobac-terial Secondary Metabolmentioning

confidence: 97%

The Cyanobacterial Origin of Potent Anticancer Agents Originally Isolated from Sea Hares

Luesch¹,

Harrigan²,

Goetz³

et al. 2002

CMC

133

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It is increasingly evident that the true biological origin of many metabolites originally isolated from certain marine macroorganisms is cyanobacterial. For example, several dolastatins, potent cytotoxic compounds originally derived from the sea hare Dolabella auricularia, have now been isolated from marine cyanobacteria of the genera Lyngbya and Symploca. This review discusses the isolation of dolastatins and close structural analogues from cyanobacteria. Biosynthetic signatures of metabolites isolated from sea hares, but which are most probably cyanobacterial in origin, are also presented. Finally, some more complex ecology involving movement of cyanobacterial metabolites through the marine food web is presented.

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Section: Biosynthetic Signatures In Cyanobac-terial Secondary Metabolmentioning

confidence: 97%

The Cyanobacterial Origin of Potent Anticancer Agents Originally Isolated from Sea Hares

Luesch¹,

Harrigan²,

Goetz³

et al. 2002

CMC

133

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“…Barbamide is strongly molluscicidal to the intermediate snail host involved in schistosomiasis, Biomphaleria glabrata. The halogen atoms comprising the unique trichloromethyl group are located at a position without an adjacent activating functionality, and this suggested a novel route for their biochemical incorporation (85,86). These barbamide halogenases and related enzymes have since been characterized as a new class of ''radical halogenases'' capable of direct halogenation of unreactive carbon atoms in natural products, such as methyl groups (87)(88)(89).…”

Section: Nanospray Fourier Transform (Ft)-ion Cyclotron Resonance Ms mentioning

confidence: 99%

Biosynthetic origin of natural products isolated from marine microorganism–invertebrate assemblages

Simmons

Coates

Clark

et al. 2008

Proc. Natl. Acad. Sci. U.S.A.

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197

181

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In all probability, natural selection began as ancient marine microorganisms were required to compete for limited resources. These pressures resulted in the evolution of diverse genetically encoded small molecules with a variety of ecological and metabolic roles. Remarkably, many of these same biologically active molecules have potential utility in modern medicine and biomedical research. The most promising of these natural products often derive from organisms richly populated by associated microorganisms (e.g., marine sponges and ascidians), and often there is great uncertainty about which organism in these assemblages is making these intriguing metabolites. To use the molecular machinery responsible for the biosynthesis of potential drug-lead natural products, new tools must be applied to delineate their genetic and enzymatic origins. The aim of this perspective is to highlight both traditional and emerging techniques for the localization of metabolic pathways within complex marine environments. Examples are given from the literature as well as recent proof-of-concept experiments from the authors' laboratories.

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“…These results point to a radical mechanism for the formation of the trichloromethyl group of barbamide. [7,8] Molecular genetic investigations on the biosyntheses of the antibiotics 7-chlorotetracycline and pyrrolnitrin have shown that haloperoxidases are not involved in the formation of these halometabolites. [9±11] During the elucidation of the pyrrolnitrin biosynthesis, the existence of halogenating enzymes, which require NADH for the catalysis of halogenation reactions, was detected.…”

mentioning

confidence: 99%

Purification and Partial Characterization of Tryptophan 7-Halogenase (PrnA) fromPseudomonas fluorescens

Keller

Wage

Hohaus

et al. 2000

Angew. Chem. Int. Ed.

180

165

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Biosynthesis of the Marine Cyanobacterial Metabolite Barbamide. 1. Origin of the Trichloromethyl Group

Cited by 89 publications

References 6 publications

The Cyanobacterial Origin of Potent Anticancer Agents Originally Isolated from Sea Hares

The Cyanobacterial Origin of Potent Anticancer Agents Originally Isolated from Sea Hares

Biosynthetic origin of natural products isolated from marine microorganism–invertebrate assemblages

Purification and Partial Characterization of Tryptophan 7-Halogenase (PrnA) fromPseudomonas fluorescens

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