Amycolatopsis orientalis Vancomycin

As recently as 1970, only about 30 naturally occurring organohalogen compounds were known. It was simply assumed that chloroform, halogenated phenols, chlorinated aromatic compounds called PCBs, and other such substances found in the environment were industrial pollutants. Now, only a third of a century later, the situation js quite different. More than 5000 organohalogen compounds have been found to occur naturally, and tens of thousands more surely exist. From a simple compound like chloromethane to an extremely complex one like vancomycin, a remarkably diverse range of organohalogen compounds exists in plants, bacteria, and animals. Many even have valuable physiological activity. Vancomycin, for instance, is a powerful antibiotic produced by the bacterium Amycolatopsis orientalis and used clinically to treat methicillin-resistant Staphylococcus aureus (MRSA). 

Vancomycin is an antibiotic produced by Streptococcus orientalis and Amycolatopsis orientalis. With the single exception of flavobacterium, it is active only against gram-positive bacteria, particularly staphylococci. Vancomycin is a glycopeptide of molecular weight 1500. It is water soluble and quite stable. 

Two biosynthetic intermediates of the vancomycin glycopeptides, SP-969 (2221) and SP-1134 (2222), are found in cultures of Amycolatopsis mediterranei (2018). This is the first reported isolation of linear biosynthetic intermediates of the vancomycin family. Monodechlorovancomycin 2223 is found for the first time in fermentation broths of Amycolatopsis orientalis (2019). The other monodechlorovancomycin was synthesized for comparison with 2223. 

Vancomycin (1, Figures 1.2 and 1.3) is a glycopeptide antibiotic with high activity against Gram-positive bacteria and is particularly renowned for its activity against the feared methicillin-resistant Staphylococcus aureus (MRSA) species [lb]. Vancomycin is produced by Amycolatopsis orientalis, a bacterium originally found in a soil... 

As a matter of fact, vancomycin (82) is produced by Amycolatopsis orientalis [80], it is only mentioned here since the strain was previously called S. orientalis. 

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... 

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. 

Vancomycin, a glycopeptide antibiotic from a fermentation broth of the actinomycete Streptomyces orientalis, later renamed No-cardia orientalis and finally reclassified as Amycolatopsis orientalis. It exhibits lethal properties against all tested strains of Staphylococcus and other Gram-positive bacteria. Despite recent incidences of bacterial resistance to vancomycin, it became almost legendary because of its performance against methicillin-resistant S. aureus (MRSA). Vancomycin and the closely related teicoplanin are typically administered parenteraUy to treat... 

CYP165B3 (OxyB) Amycolatopsis orientalis ILFK, 1LG9, ILGF Oxidative phenol coupling of CD-rings in vancomycin biosynthesis [248]... 

CYP165C4 (OxyC) Amycolatopsis orientalis lUED Biaryl cyclization of AB-rings in vancomycin biosynthesis [249]... 

Two new glycopeptide antibiotics, MM 47761 and MM 49721, have been isolated from a new strain of Amycolatopsis orientalis they are relatives of vancomycins, containing the disaccharide 0-Of-L-Rham -(l- 2)-0-yS-D-Glc -( - attached to a heptapeptide nucleus, with epi-... 

Vancomycin Amycolatopsis orientalis Entrapment in calcium alginate beads adsorption on synthetic cotton fibers, glass wool, and cotton cloth [64]... 

Glycopeptides. Among the vast class of peptide antibiotics, the only ones commonly used are members of this family, denoted as dalbaheptides in view of their mechanism of action (d-aknine-D-alanine Mnding) and their composition (heptapeptides). The most well known are vancomycin and teicoplanin, produced by Amycolatopsis orientalis and Actinoplanes teichomyceticus, respectively (O Fig. 9.6). 

Solid-phase Semi-Synthesis of Vancomycin Vancomycin was first isolated in 1953 by Edmund Kornfeld, at Eli Lilly (Indianapolis, IN), from Amycolatopsis orientalis... 

The glycopeptide antibiotics include avoparcin, teicoplanin, and vancomycin. Avoparcin is produced by Amycolatopsis coloradensis, while teicoplanin is a mixture of six closely related compounds produced by Streptococcus teichomyetius. Vancomycin is produced by Streptococcus orientalis. 

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