Nocardia orientalis

A51568A (A/-demethyl-vancomycin), B Nocardia orientalis N RRL 15232 1982 Lilly 39,40... 

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

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]. 

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... 

At the other extreme, Borghi et al. reported the biotransformation of the teicoplanin family of antibiotics. They found that these large, complex glyco-peptides produced by Actinoplanes teichomyceticus could be demannosylated by cultures of Nocardia orientalis NRRL 2450, or Streptomyces candidus NRRL 3218. Interestingly, they also found that the demannosylated teicoplanin and other de-mannosylated derivatives could be converted back to the mannosylated form by the original producing organism (31). 

Vancomycin is produced by fermentation Amycolatopsis orientalis (formeriy Nocardia orientalis). it has been avaiiabie for approximateiy 40 years, but its popuiarity has increased significantiy with the emergence of MRSA in the eariy 1980s. Chemicaiiy, vancomycin has a giycosy iated hexapeptide chain that is rich in unusuai amino acids, many of which contain aromatic rings cross-iinked by aryi ether bonds into a rigid moiecuiar framework. 

Nanjo, R, Katsumi, R., and Sakai, K. 1990. Purification and characterization of an exo-P-D-glucosaminidase, a novel type of enzyme, from Nocardia orientalis. J Biol Chem 265 10088-10094. 

Usui, T., Hayashi, Y, Nanjo, R, Sakai, K., and Ishido, Y. 1987. Transglycosylation reaction of a chitinase purified from Nocardia orientalis. Biochim Biophys Acta 923 302-309. 

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