Rimocidin. I. Carbon Skeleton, Partial Structure, and Absolute Configuration at C-27<sup>1</sup>

Cope, Arthur C.; Burrows, Elizabeth P.; Derieg, M. E.; Moon, Sung; Wirth, W.

doi:10.1021/ja00951a036

Cited by 40 publications

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“…Rimocidin ( 1 ) is a 28‐membered polyene macrolide which was isolated from Streptomyces rimosus in 1951 8. Cope et al established the carbon skeleton in the mid‐1960s,9 and its flat structure was determined independently by the groups of Borowski and Rinehart in the 1970s 10. The stereochemistry of rimocidin was determined by Borowski and co‐workers group in 1995 through 2D NMR analysis 11.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Rimocidinolide Methyl Ester, the Aglycone of (+)‐Rimocidin

Packard

Vescovi

et al. 2004

Angew Chem Int Ed

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Section: Methodsmentioning

confidence: 99%

Synthesis of Rimocidinolide Methyl Ester, the Aglycone of (+)‐Rimocidin

Packard

Vescovi

et al. 2004

Angew Chem Int Ed

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“…The partial structure of rimocidin was elucidated by Cope and colleagues (47) and by Pandey and Rinehart (170), although absolute stereochemical assignments of the 28-membered aglycone rimocidinolide came later (209). Recently, rimocidin production by Streptomyces diastaticus var.…”

Section: Gene Disruptions In the Rimocidin Biosynthetic Gene Clustermentioning

confidence: 99%

Genetics ofStreptomyces rimosus, the Oxytetracycline Producer

Petković

Cullum

Hranueli

et al. 2006

Microbiol Mol Biol Rev

101

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SUMMARY From a genetic standpoint, Streptomyces rimosus is arguably the best-characterized industrial streptomycete as the producer of oxytetracycline and other tetracycline antibiotics. Although resistance to these antibiotics has reduced their clinical use in recent years, tetracyclines have an increasing role in the treatment of emerging infections and noninfective diseases. Procedures for in vivo and in vitro genetic manipulations in S. rimosus have been developed since the 1950s and applied to study the genetic instability of S. rimosus strains and for the molecular cloning and characterization of genes involved in oxytetracycline biosynthesis. Recent advances in the methodology of genome sequencing bring the realistic prospect of obtaining the genome sequence of S. rimosus in the near term.

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“…In membranes formed from lipid solutions containing equimolar amounts of cholesterol and phospholipid, this compound produced striking membrane instability (defined in Table V), but did not modify significantly either the total electrical membrane conductance or individual ionic conductances (3). Rimocidin is a tetraene antibiotic having a 28-membered lactone ring, 8 hydroxyl substituents, an amino substituent but no carboxyl group (22), while the tetraene antibiotic PA-166 contains both amino and carboxyl substituents (19). The effects of these two compounds on the permeability properties of these membranes are shown in Table V.…”

Section: Membrane Permeabilitymentioning

confidence: 99%

Molecular Aspects of Polyene- and Sterol-Dependent Pore Formation in Thin Lipid Membranes

Dennis

Stead

Andreoli

1970

The Journal of General Physiology

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Amphotericin B modifies the permeability properties of thin lipid membranes formed from solutions containing sheep red cell phospholipids and cholesterol. At 10 -6 M amphotericin B, the DC membrane resistance fell from 10 s to 102 ohm-cm', and the membranes became C1--, rather than Na+ -selective; the permeability coefficients for hydrophilic nonelectrolytes increased in inverse relationship to solute size, and the rate of water flow during osmosis increased 30-fold. These changes may be rationalized by assuming that the interaction of amphotericin B with membrane-bound sterol resulted in the formation of aqueous pores. N-acetylamphotericin B and the methyl ester of N-acetylamphotericin B, but not the smaller ring compounds, filipin, rimocidin, and PA-166, produced comparable permeability changes in identical membranes, and amphotericin B and its derivatives produced similar changes in the properties of membranes formed from phospholipid-free sterol solutions. However, amphotericin B did not affect ionic selectivity or water and nonelectrolyte permeability in membranes formed from solutions containing phospholipids and no added cholesterol, or when cholesterol was replaced by either cholesterol palmitate, dihydrotachysterol, epicholesterol, or A5-cholesten-3-one. Phospholipid-free sterol membranes exposed to amphotericin B or its derivatives were anion-selective, but the degree of C1-selectivity varied among the compounds, and with the aqueous pH. The data are discussed with regard to, first, the nature of the polyene-sterol interactions which result in pore formation, and second, the functional groups on amphotericin B responsible for membrane anion selectivity.

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Rimocidin. I. Carbon Skeleton, Partial Structure, and Absolute Configuration at C-27¹

Cited by 40 publications

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Synthesis of Rimocidinolide Methyl Ester, the Aglycone of (+)‐Rimocidin

Synthesis of Rimocidinolide Methyl Ester, the Aglycone of (+)‐Rimocidin

Genetics ofStreptomyces rimosus, the Oxytetracycline Producer

Molecular Aspects of Polyene- and Sterol-Dependent Pore Formation in Thin Lipid Membranes

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Rimocidin. I. Carbon Skeleton, Partial Structure, and Absolute Configuration at C-271

Cited by 40 publications

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Synthesis of Rimocidinolide Methyl Ester, the Aglycone of (+)‐Rimocidin

Synthesis of Rimocidinolide Methyl Ester, the Aglycone of (+)‐Rimocidin

Genetics ofStreptomyces rimosus, the Oxytetracycline Producer

Molecular Aspects of Polyene- and Sterol-Dependent Pore Formation in Thin Lipid Membranes

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Rimocidin. I. Carbon Skeleton, Partial Structure, and Absolute Configuration at C-27¹