Lipopeptide antibiotics

Baltz, R.H., Miao, V. and Wrigley, S.K. (2005) Natural products to drugs daptomycin and related lipopeptide antibiotics. Natural Product Reports, 22, 717. 

Miao, V., Brost, R., Chappie, J. et al. (2006) The lipopeptide antibiotic A54145 biosynthetic gene cluster from Streptomyces fradiae. Journal of Industrial Microbiology Biotechnology, 33, 129. 

Muller, C., Nolden, S., Gebhardt, P. et al. (2007) Sequencing and analysis of the biosynthetic gene cluster of the lipopeptide antibiotic friulimicin in Aclinoplanesfriuliensis. Antimicrobial Agents and Chemotherapy, 51, 1028. 

Coeffet-Le Gal, M.F., Thurston, L., Rich, P. et al. (2006) Complementation of daptomycin dpt A and dptD deletion mutations in trans and production of hybrid lipopeptide antibiotics. Microbiology (Reading, England), 152,2993. 

Miao, V., Coeffet-Le Gal, M.-F., Nguyen, K. et al. (2006) Genetic engineering in Streptomyces roseosporus to produce hybrid lipopeptide antibiotics. Chemistry Biology, 13, 269. 

Grunewald, J., Sieber, S.A., Mahlert, C. et al. (2004) Synthesis and derivatization of daptomycin a chemoenzy-matic route to acidic lipopeptide antibiotics. Journal of the American Chemical Society, 126, 17025. 

One of the most characteristic features of FRET is its sensitive dependency on the fluorophore distance. This is advantageously used to evaluate structures and conformational changes of peptides, glycopeptides, and proteins among other molecules [164-166], The conformational change of the lipopeptide antibiotic daptomycin from an inactive linear form to a biological active cyclic form... 

Echinocandins B-D -lipopeptide antibiotics and other peptides including aculeacin A, mulundocandin, and pneumocandins... 

Aretz W, Meiwes J, Seibert Q Vobis Ci Wink J. (2000) Frinlimicins novel lipopeptide antibiotics with peptidoglycan synthesis inhibiting activity from Actinoplanes Friuliensis sp nov. J Antibiot 53 807-815. 

A novel cyclic lipopeptide antibiotic was isolated from cultures of Strep-tomyces roseosporus grown in the presence of decanioc acid. Daptomycin interacts with the bacterial cell membrane and interferes with membrane potential.Unlike polymyxin B, daptomycin can target majority of clinically relevant Gram-positive pathogens. 

H Takeshima, J Inokoshi, Y Takada, H Tanaka, S Omura. A deacylation enzyme for aculeacin A, a neutral lipopeptide antibiotic, from Actinoplanes utahensis purification and characterization. J Biochem 105 606-610, 1989. 

Daptomycin is a novel lipopeptide antibiotic, an inhibitor of lipoteichoic acid synthesis, with potent bactericidal activity against most clinically important Gram-positive bacteria, including resistant strains (1,2). 

Recent studies on the mechanism of biosynthesis of cyclic lipopeptide antibiotics have proved that these are systematically synthesized by the multifunctional proteins, non-ribosomal peptide synthetase (NRPS). 

Cyclic lipopeptide antibiotics can be classified structurally into several groups. The enormous structural diversity in this group of antibiotics leads... 

Cyclic lipopeptide antibiotics contain various kinds of amino acids including unusual amino acids. Many kinds of cyclic lipopeptides were discovered from microorganisms and they often exhibit a wide variety of biological activities such as antimicrobial, antifungal, antitumor, and enzyme inhibitory activities. It is also of considerable interest that the structural similarities do not always reflect any similarity of biological activities in the cyclic lipopeptides. 

The structural and biological diversity of the cyclic lipopeptide antibiotics is extremely attractive to chemical, pharmacological and medical sciences. Future rational drug design, chemical modification and discovery of novel cyclic lipopeptides from natural sources will give rise to useful biological tools for research and development in the medicinal sciences. 

Mizumoto, S., Hirai, M., and Shoda, M. (2006). Production of lipopeptide antibiotic iturin A using soybean curd residue cultivated with Bacillus subtilis in solid-state fermentation. Appl. Microbiol. Biotechnol. 72, 869-875. 

This group of lipopeptide antibiotics produced by Streptomyces fradiae spawned a wide number of analogs produced by feeding various fatty acids (Fig. 7). In addition, the ratios of the various natural metabolites could be controlled by addition of valine or isoleucine (18). 

Boeck, L. D. and Betzel, R. W. (1990) A54145, a new lipopeptide antibiotic complex factor control through precursor directed biosynthesis. J. Antibiot. 43,607-615. 

Daptomycin was originally isolated from the soil saprotroph Streptomyces roseos-porus by scientists at Eli Lilly and Company in the 1980s. It is a novel lipopeptide antibiotic used in the treatment of certain infections caused by Gram-positive organisms. The proposed mechanism of action involves insertion of the lipophilic daptomycin tail into the bacterial cell membrane, causing rapid membrane depolarization and a potassium ion efflux. This leads to the arrest of DNA, RNA, and protein synthesis, resulting in bacterial cell death (see footnote 1). 

Tricyclic spiroketal glycosides from cultures of Pa-pularia sphaerosperma. The P, have antibiotic activities. Similar to the lipopeptide antibiotic echinocandin B, they inhibit the biosynthesis of /S- glucans in yeasts. 

A lipopeptide antibiotic complex from cultures of Bacillus cereus. As phospholipase A2, C, and D inhibitors the P. have antiallergic and bronchodilatory activities. They are yellow solids and have been characterized as the potassium salts, see formula and table. UL J. Antibiot. (Tokyo) 39, 737, 745, 755, 860 (1986). -[HS 294190]... 

C52Hg5N 022 M 1216.304 Cyclic lipopeptide antibiotic. Prod, by P.seudomonas cepacia. Antifungal agent. Powder. Mp 210-214°. [x l + 20.8 (H2O). r-Deoxy Cepacidin A-,... 

Lipopeptide antibiotic. Prod, by Myxococcus virescens. [(xf -33 (c, 0.1 in MeOH). 

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