Streptomyces rimosus

Bacterium Streptomyces rimosus Soybean meal Carelose (glucose)... 

Streptomyces peucetius var. caesius Doxorubicin Streptomyces rimosus Oxytetracycline Streptomyces rimosus forma paromomycinus Paromomycin... 

Tetracycline Streptomyces rimosus Broad spectrum Protein synthesis... 

From fermentation solutions of Streptomyces rimosus forma paromomycinus or Streptomyces krestomyceticus N.C.LB. 8995. 

Highly active super strains, such as Cunninghamella sp., Beauveria bassiana and Streptomyces rimosus, are particularly useful here, as they tend to produce multiple metabolites thus, the majority of the desired metabolites can be obtained with a minimal number of incubations. 

Streptomyces griseolus Streptomyces platensis Streptomyces rimosus Streptomyces roseochromogenus Streptomyces rimosus... 

Canned, R.J., Knaggs, A.R., Dawson, M.J. et al. (1995) Microbial biotransformation of the angiotensin II antagonist GR117289 by Streptomyces rimosus to identify a mammalian metabolite. Drug Metabolism and Disposition The Biological Fate of Chemicals, 23, 724—729. 

Cannel, R.J.P., Rashid, T., Ismail, I.N. et al. (1997) Novel metabolites of warfarin produced by Beauveria bassiana and Streptomyces rimosus a novel application of HPLC-NMR. Xenobiotica The Fate of Foreign Compounds in Biological Systems, 27, 147-157. 

Oxytetracycline occurs as yellow crystals or crystalline powder, has a bitter taste and is odorless. Oxytetracycline hydrochloride should have potency not less than 835 pg C22H24N2O9 per mg [1], whilst for oxytetracycline not less than 832 pg/g [1] or 95.0-102.0% as anhydrous substance [2] or not less than 88.0% of C22H24N2O9 calculated as anhydrous basis [3,4]. For oxytetracycline calcium, it should contain not less than 90.0% and not more than 100.5% [2], or 865 pg C22H24N2O9 per mg [1]. Oxytetracycline was produced by the growth of certain strain of Streptomyces rimosus or obtained by other means. 

Clark et al. [81] determined the time course of A-acetylation of primaquine by Streptomyces roseochromogenous and Streptomyces rimosus by quantitative high performance liquid chromatographic analyses of the culture broths. The A-5-bistri-fluoroacetyl derivative of primaquine was used as an internal standard in the analysis for the quantitation of primaquine A-acetate in microbial culture broths. S. roseochromogenous forms the highest level of primaquine A-acetate at 24—36 h after substrate addition, while S. rimosus is slower in its acetylation, peaking at 3 days after substrate addition. The formation of a novel dimeric compound from the reaction of primaquine with 8-(4-phthalimido-l-methylbutylamino)-6-methoxy quinoline is also reported. 

When (V-acetylprimaquine (175) was incubated for prolonged periods of time with Candida tropicalis (ATCC 20021) (232) and Streptomyces rimosus (ATCC 23955) (233), two unusual minor dimeric metabolites were obtained. These were identified as the methylene-linked compound 177 formed by C. tropicalis and the biaryl-linked compound 178 formed by 5. rimosus. Both dimeric metabolites were prepared synthetically to confirm their identities. 

Tetracyclines are a group of antibiotics derived from bacteria. Chlortet-racycline was isolated from Streptomyces aureofaciens and oxytetracycline from Streptomyces rimosus. Tetracychnes act by binding to receptors on the bacterial ribosome and inhibit bacterial protein synthesis. 

N-Acetylation (Streptomyces roseo chromogenus) Oxidative deamination to carboxylic acid Aspergillus flavus) 5,5 -Dimerization Streptomyces rimosus, Candida tropicalis) Oxidative deamination to carboxylic acid and amide formation Streptomyces rimosus)... 

Saccharomyces cerevisiae) C-8 (S) Hydroxylation Streptomyces rimosus) 2,4-0-methylation and 2-0-methylation,4-0-glucosylation [126,127]... 

TABLE 2.10. Proteins Encoded in the Genomic Area Covering the / ar-Cluster of Streptomyces rimosus subsp. paromomycinus NRRL 2455 (Accession Code AJ628955) ... 

The first antibiotic of the tetracycline series, chlorotetracycUne, which was isolated from a culture liquid of Streptomyces aureofaciens, was introduced into medical practice in 1948. Conseqnently, there were another six dmgs of the tetracycline series that were introdnced into medical practice between 1950 and 1972. Oxytetracycline is isolated from Streptomyces rimosus tetracycline (semisynthetic), demeclocycline is isolated from the mutant type of S. aureofaciens methacycUne (semisynthetic), doxycycUne (semisynthetic), and minocycline (semisynthetic). Methods of synthesis of the tetracycline series antibiotics have been sng-gested however, they are purely of an academic interest and do not have any practical valne. 

Streptomyces aureofaciens, then oxytetracycline was derived from Streptomyces rimosus and then tetracycline was obtained by catalytic dehalogenation of chlortetracycline. They are classified as in table 9.2.1. 

Cultures of Streptomyces rimosus var paromomycinus characteristically develop UV absorption at 240 and 278 nm due to formation of malonomicin (22), a compound that shows antiprotozoal activity towards Trypanosoma congolense, the causative agent of sleping sickness in cattle [42]. Malonomicin contains an unique aminomalonic acid unit that, on brief heating in water, undergoes decarboxylation and results in a compound devoid of biological activity [43]. Hydrolysis of the compound yielded L-serine and racemic aspartic acid. The structure was elucidated by chemical and spectroscopic methods [43,44] and was confirmed by total synthesis [45]. 

Trew SJ, Wrigley SK, Pairet L, Sohal J, Shanu-Wilson P, Hayes MA, Martin SM, Manohar RN, Chicarelli-Robinson MI, Kau DA, Byrne CV, Wellington EMH, Moloney JM, Howard J, Hupe D, Olson ER (2000) Novel Streptopyrroles from Streptomyces rimosus with Bacterial Protein Histidine Kinase Inhibitory and Antimicrobial Activities. J Antibiot 53 1... 

Raggatt ME, Simpson TJ, Wrigley SK (1999) Biosynthesis of XR587 (Streptopyrrole) in Streptomyces rimosus Involves a Novel Carbon-to-Nitrogen Rearrangement of a Proline-Derived Unit. Chem Commun 1039... 

During the course of experiments for the elucidation of the structure of the two earlier discovered compounds chlortetracycline (CTC) and oxytetracycline (OTC) it was found that hydrogenation of chlortetracycline resulted in halogenolysis and the product tetracycline (TC) retained the useful activity spectrum of the first two members of the family. TC appears to represent the first clinically successful antibiotic produced by shere chemical manipulation of preexisting antibiotic. TC was found to be present in fermentations of both cultures streptomyces aureofaciens and streptomyces rimosus as well as in streptomyces viridofaciens (1). 

Bacterium Streptomyces rimosus forma paromomycinus Manufacturing Process... 

The medium is cooled and inoculated with 20 ml of a suspension of the spores from two Mover s sporulation agar slant cultures of Streptomyces rimosus forma paromomycinus in sterile 0.1% sodium heptadecyl sulfate solution. The inoculated culture mixture is incubated at 26°C for sixty hours during which time the mixture is stirred at 200 rpm and sterile air is passed into the medium through the sparger at the rate of 12 liters per minute. A portion of the resulting incubated culture mixture is employed for inoculation of 16 liters of a nutrient medium having the following composition ... 

Cunninghamella blakesleeana ATCC 9245 Cmninghamella blakesleeana NRRL 1369 Streptomyces rimosus ATCC 23955... 

A fermentation process was developed for the production of epothilone B, and the titer of epothilone B was increased by a continuous feed of sodium propionate during fermentation. The inclusion of XAD-16 resin during fermentation to adsorb epothilone B and to carry out volume reduction made the recovery of product very simple (Benigni et al., 2004). A microbial hydroxylation process was developed for the conversion of epothilone B (10) to epothilone F (11) by Amycolatopsis orientalis SC 15847. A bioconversion yield of 37-47 % was obtained when the process was scaled up to 100-250 L. Recently, epothilone B hydroxylase and the ferredoxin gene have been cloned and expressed in Streptomyces rimosus from Amycolatopsis orientalis SC 15847 by our colleagues in Bristol-Myers Squibb. Mutants and variants thereof this cloned enzyme has been used in the hydroxylation of epothilone B to epothilone F to obtain even higher yields of product (Basch et al, 2004). 

Diastereoselective hydroxylations are more common, for example Streptomyces rimosus (NRRL 2234) will hydroxylate zearalenone (25) to give the (S)-8 -hydroxy derivative (26 equation 7). Other microorganisms gave reduction of the 6 -ketone group in (25). 

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