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ChemicalBook CAS DataBase List Natamycin
7681-93-8

Natamycin synthesis

1synthesis methods
Natamycin, a mixture of stereoisomeric 22-[(3-amino-3,6-dideoxy-β-Dmannopyranosyl)oxy]-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.0.5,7]-octacosa-8,14,16,18,20,penten-25-carboxylic acid (35.1.3), like amphotericin and nystatin, is a polyene antibiotic that is isolated from the products of the vital activity of the actinomycete Streptomyces natalensis.
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Yield:-

Reaction Conditions:

with Streptomyces sp. RGU5.3Product distribution / selectivity;Microbiological reaction;Enzymatic reaction;

Steps:


Figure 3 shows the biological activities of the polyenes pimaricin (IVa) and AB-400 (IVb) isolated from Streptomyces sp. RGU5.3. It shows the HPLC analysis (chromatograms) of the fermentation cultures coming from Streptomyces sp. RGU5.3 grown in medium with acetate (Figure 3A) or glucose (Figure 3B) as source of carbon, respectively; The same results were obtained comparing pimaricin (IVa) and its amidated derivative AB-400 (IVb). Both compounds were purified starting from the isolated strain Streptomyces sp. RGU5.3, as indicated in the section on Experimental Methods. The strain was cultivated in a medium supplemented with both glucose and sodium acetate, and it was found that the production of the amidated derivative was highly increased when the sodium acetate was added to the culture. In this way, using a fermentation culture containing glucose as the source of carbon and not sodium acetate, the pimaricin/AB-400 balance is 70/30; when the same medium is supplemented with sodium acetate, the production profile is reversed, being AB-400 (IVb) the main polyene compound produced (Figure 3).

References:

Consejo Superior de Investigaciones Cientificas (CSIC) EP1862467, 2007, A2 Location in patent:Page/Page column 5; 24; 29

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