Nocardia antibiotic

Kanglemycin. Kanglemycia (74) (Fig. 8) is isolated from the fermentation broth filtrate of Nocardia mediterranei var kanglensis (1747-64) and its stmcture determiaed by x-ray crystallographic studies. The antibiotic is active against gram-positive bacteria (28). 

Allenes are compounds with adjacent carbon-carbon double bonds. Many allenes are chiral, even though they don t contain chirality centers. Mycomycin, for example, a naturally occurring antibiotic isolated from the bacterium Nocardia acidophilus, is chiral and has = -130. Explain why mycomycin is chiral. Making a molecular model should be helpful. 

Amphoteric glycopeptid antibiotic from Nocardia orientalis (NRRL 2450, 2451, 2452). 

Liu WC, Fisher SM, Wells JS Jr, Ricca CS, Principe PA, Trejo WH, Bonner DP, Gougoutos JZ, Toeplitz BK, Sykes RB (1981) Siderochelin, a New Ferrous-ion Chelating Agent Produced by Nocardia. J Antibiot 34 791... 

Murakami Y, Kato S, Nakajima M, Matsuoka M, Kawai H, Shin-Ya K, Seto H (1996) Formobactin, a Novel Free Radical Scavenging and Neuron Cell Protecting Substance from Nocardia sp. J Antibiotics 49 839... 

Nemoto A, Hoshino Y, Yazawa K, Ando A, Mikami Y, KomaM H, Tanaka Y, Grafe U (2002) Asterobactin, a New Siderophore Group Antibiotic from Nocardia asteroides. J Antibiotics 55 593... 

Mukai A, Komaki H, Takagi M, Shin-ya K (2009) Novel Siderophore, JBIR-16, Isolated from Nocardia tenerifemis 101015. J Antibiot 62 601... 

Rifamycin SV (133, Fig. 23) is a naturally occurring macrocycle isolated from Nocardia mediterranei by Senti, Greco and Ballotta in 1959. It shows a high in vitro antibiotic activity through inhibition of DNA-dependent RNA polymerase, but bioavailability is low due to its poor water solubility. The semisynthetic derivative rifampicin (135) displays markedly higher water solubility and in vivo activity. We chose 3-formylrifamycin (134) as model macrocycle for the possibility of binding it to solid phase by hydrazone bond formation in a manner similar to rifampicin (Fig. 24). 

Vancomycin Vancomycin (32.7.2) was isolated in 1956 from the products of the functional activity of actinomycetes Streptomyces orientalis (cnrrently Nocardia orientalis). Based on its chemical structure and contents, vancomycin is classified as a glycopeptide antibiotic. Its molecular mass is significantly more than practically any other used antibiotics [325-330]. 

Rifampicin is a semisynthetic derivative of rifamicin B, a macrolactam antibiotic and one of more than five antibiotics from a mixture of rifamicins A, B, C, D, and E, which is called a rifamicin complex, which is produced by actinomycetes Streptomyces mediteranei (Nocardia mediteranei). It was introduced into medical practice in 1968. Synthesis of rifampicin begins with an aqueous solution of rifamicin, which under the reaction conditions is oxidized to a new derivative of rifamicin S (32.7.4), with the intermediate formation of... 

Hoshino Y, Mukai A, Yazawa K, Uno J, Ishikawa J, Ando A, Fukai T, Mikami Y (2004) Transvalencin A, a Thiazolidine Zinc Complex Antibiotic Produced by a Clinical Isolate of Nocardia transvalensis I. Taxonomy, Fermentation, Isolation and Biological Activities. J Antibiot 57 797... 

The rifamycins are ansamycin antibiotics produced by cultures of Amycolatopsis mediterranei (formerly Nocardia mediterranei or Streptomyces mediterranei). The crude antibiotic mixture was found to contain five closely related substances rifamycins A-E, but if the organism was cultured in the presence of sodium diethyl barbiturate (barbitone or barbital), the product was almost entirely rifamycin B (Figure 3.71). Rifamycin B has essentially no antibacterial activity, but on standing in aqueous solution in the presence of air, it is readily transformed by oxidation and intramolecular nucleophilic addition into rifamycin O, which... 

A main component of the linear ferrioxamine group (63). Reverses inhibition by ferrimycin antibiotics (148) and acts as a growth factor for Microbacterium lacticum (101). From Streptomyces pilosus (8). Also produced by species of Nocardia and Micromonospora, and by a number of species of Streptomyces (148). 

Lancini, G., Sartori, G. Rifamycin G, a further product of Nocardia mediterranei metabolism. J. Antibiotics 29,466 (1976)... 

Mycomycin is a naturally occurring antibiotic produced by the fungus Nocardia acidophilus. The molecular formula of the substance is Ci3Hi0O2, and its systematic name is 3,5,7,8-tridecatetraene-10,12-diynoic acid. Draw the structure of mycomycin. 

Harada K, Tomita K, Fuji K, Sato N, Uchida H, Yazawa K, Mikami Y. Inactivation of fusidic acid by pathogenic Nocardia. J Antibiot (Tokyo) 1999 52(3) 335-9. 

Hartmann A, Halvorsen CE, Jenssen T, Bjorneklett A, Brekke IB, Bakke SJ, Hirschberg H, Tonjum T, Gaustad P. Intracerebral abscess caused by Nocardia otitidiscaviarum in a renal transplant patient—cured by evacuation plus antibiotic therapy Nephron 2000 86(l) 79-83. 

The antibiotic thiolactomycin 39 (Figure 9.9), a fermentation product from a Nocardia species containing an unusual thiolactone moiety, was discovered in 1981 [49,50]. It resembles a... 

The antibiotic thiolactomycin (43), a fermentation product from a Nocardia species containing an unusual thiolactone moiety was patented as antibiotic no. 2-200 and subsequently reported in the literature in 1982 [73,74]. It resembles a sugar-derived a,/3-unsaturated 4-thioglycono-1,4-lactone and was found to be a broad-spectmm antibiotic [75] by interference with the fatty acid metabolism of bacteria and also inhibited inducible /3-lactamases [76]. A de novo synthesis of the racemate was reported by a Du Pont group in 1984 [77]. Chambers and Thomas [78] reported the synthesis of the (55j-enantiomer in 1989 and concluded from its optical rotation that the natural product is the (5i )-enantiomer. 

Vancomycin was discovered in the 1950s in a soil sample collected in the jungle of Borneo and isolated by Eli Lilly from culture broth of the actinomycete Streptomyces orientalis, which was later named Nocardia orientalis and finally Amycolatopsis orientalis. It was first used in clinics in 1959, and today also teicoplanin (O Fig. 25) is being used clinically. The other gly-copeptides of the vancomycin group such as ristocetin A (O Fig. 26) have too many toxic side effects to be used as a therapeutic. Vancomycin and teicoplanin are among the last antibiotics... 

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