Streptomyces citricolor

Abel, C.B.L., Lindon, J.C., Noble, D., Rudd, B.A.M., Sidebottom, P.J., and Nicholson, J.K, Characterization of metabolites in intact Streptomyces citricolor culture supernatants using high-resolution nuclear magnetic resonance and directly coupled high-pressure liquid chromatography-nuclear magnetic resonance spectroscopy, Anal. Biochem., 270, 220, 1999. 

Winson MK, Todd M, Rudd BAM, Jones A, Alsberg BK, Woodward AM, Goodacre R, Rowland JJ, Kell DB (1998) A DRASTIC (Diffuse Reflectance Absorbance Spectroscopy Taking in Chemometrics) approach for the rapid analysis of microbial fermentation products quantification of aristeromycin and neplanocin A in Streptomyces citricolor broths. In Kieslich, K (ed) New Frontiers in Screening for Microbial Biocatalysts. Elsevier Science B.V., The Netherlands, p 185... 

Naturally occurring (l S, 25, 3i )-4-hydroxymethylcyclopent-4-ene-l,2,3--triol (950) plays a central role in the ability of a non-aristeromycin producing mutant strain of Streptomyces citricolor to support production of both aristeromycin and neplanocin. Swem oxidation of readily available 13 from L-tartaric acid provides the aldehyde 943 which, when treated with an excess of propargyl zinc bromide, leads to a 2.3 1 diastereomeric mixture of acetylenic alcohols 944. Silylation of the hydroxyl group with TBSOTf and subsequent saponification of the ester group yields the carboxylic acid 945 in 74% overall yield from 13. Interestingly, Dess-Martin oxidation of 943 provides the allenic ketone 946, which is unstable to base and cannot be used in the subsequent radical cyclizations. 

A DRASTIC (Diffuse Reflectance Absorbance Spectroscopy Taking In Chemometrics) Approach for the Rapid Analysis of Microbial Fermentation Products Quantification of Aristeromycin and Neplanocin A in Streptomyces citricolor Broths. 

Aristeromycin and neplanocin A (Figure 1) are naturally occurring carbocyclic nucleosides produced by Streptomyces citricolor (reviewed in [2]). Both molecules have a close structural similarity to adenosine and possess potent biological activity, including inhibition of 5-adenosylhomocysteine hydrolase [3]. Neplanocin A also exhibits anti-tumour... 

Streptomyces citricolor strains were grown in GAM medium (glucose 60g Arkasoy 50, 60g MOPS, 21g per litre water, pH7.0) in duplicate 250ml fermentation flasks at 28°C. Samples extracted after 3 and 6 days incubation were centrifuged and the supernatant diluted 1 20 in a 1 1 mixture of methanol and mobile phase (20% acetonitrile containing 3g/l SDS,... 

Prod, by Streptomyces citricolor. Likely precursor of Aristeromycin, A-02729. Oil. 

The synthesis of the amine triol (59) has been described and used to demonstrate that its a biosynthetic precursor of aristeromycin in Streptomyces citricolor ... 

Nucleosides in which the ribofiiranosyl oxygen is replaced by a methylene to result in a cyclopentane ring are referred to as carbocyclic nucleosides. The first such conopound was carbocyclic adenosine (1, aristeromycin), which was synthesized in its racemic form prior to isolation of the (-)-enantiomer from Streptomyces citricolor. The antiviral activity of has stimulated the search for other carbocyclic nucleosides that would display a more favorable therapeutic index. ... 

Cyclopentane and Cyclobutane Derivatives.-The isolation of the unsaturated cyclitol 59 from Streptomyces citricolor has been described and proposed as a biosynthetic precursor of aristeromycin and neplanocin A. 

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