Chromobacterium violaceum

Phenylalanine is hydroxylated to tyrosine and then sequentially to 4-hydroxyphenyl-pyruvate and by dioxygenation and rearrangement to 2,5-dihydroxyphenylpyruvate (Figure 3.16) (Arias-Barrau et al. 2004). Hydroxylation involves 6,7-dimethyltetrahydro-biopterin that is converted into the 4a-carbinolamine (Song et al. 1999). Copper is not a component of the active enzyme, although there is some disagreement on whether or not Fe is involved in the reaction for the hydroxylase from Chromobacterium violaceum (Chen and Frey 1998). 

Chen D, PA Frey (1998) Phenylalanine hydroxylase from Chromobacterium violaceum. Uncoupled oxidation of tetrahydropterin and the role of iron in hydroxylation. J Biol Chem 273 25594-25601. 

Ein Aminozucker, der von Glucosamin und Galaktosamin verschieden ist, jedoch bei der ELSON-MoRGAN-Reaktion einen Farbstoff mit gleichem Absorptionsspektrum wie Glucosamin bildet, ist im spezifischen Lipopolysaccharid einiger Stamme von Chromobacterium violaceum enthalten. 

Fig. 10.—Chemical structure oflipid A of Chromobacterium violaceum. The dashed line indicates nonstoichiometric a-hydroxylation (85) of 12 0. For details, see the text, and for substitutents of phosphate residues, see Table I.

After 5 years in the FDA s fast track development program, Romidepsin (Fig. 18) was approved by the FDA for refractory cutaneous T-cell lymphoma on November 6,2009. In the literature, romidepsin has also been called depsipeptide, FK228, FR901228, and NSC-630176. It was isolated from bacterial fermentation extracts from Chromobacterium violaceum and is a potent inhibitor of HDAC. In some human cancer cell lines, romidepsin inhibits HDACs at levels ten times that of TSA. 

A group of related siderophores comprises the desferri- or deferriferrioxamines (occasionally abbreviated as desferrioxamines) or proferrioxamines. Originally they were obtained from Actinomycetes, mainly Nocardia and Streptomyces spp. (187) and later found to be produced also by Erwinia spp. (several representatives) (e.g. (30a, 113,115,180)), Arthrobacter simplex (B), Chromobacterium violaceum (E) (246a), and by Pseudomonas stutzeri (several) (229a, 246,398). They consist of three (or in rare cases four) mono-N-hydroxy-l,4-diaminobutane (putrescine), mono-iV-hydroxy-l,5-diaminopentane (cadaverine) or (rarely) mono-N-hydroxy-1,3-diaminopropane units connected by succinic acid links. The hydroxylated terminus carries an acetyl or a succinyl (as in the structural formula heading Table 6)... 

Romidepsin (4) is a natural product produced by Chromobacterium violaceum and was shown to display potent antitumor activity both in vitro (IC5o = 0.55-4.4 nM), and in vivo where growth of mouse and human tumors in mice was inhibited [68]. 

Ueda, M., Manda, T., Matsumoto, S., Mukumoto, S., Nishigaki, F., Kawamura, 1. et al. (1994) FR901228, a novel antitumor bicydic depsipeptide produced by Chromobacterium violaceum No. 968. 111. Antitumor activities on experimental tumors in mice. Journal of Antibiotics (Tokyo), 47, 315-323. 

Some types of microorganisms, in particular Chromobacterium violaceum, which in the process of performing vital functions can synthesize specific beta-lactam antibiotics that have a monocyclic structure are called monobactams. Nocardicins, in particular nocardicin A, are examples of such monobactams. 

Overview of AAH crystal structures deposited in the protein databank from human (h), rat (r), Chromobacterium violaceum (cv), Colwellia psychrerythraea... 

Chromobacterium violaceum (enantioselective) Chromobacterium viscosum (enantioselective)... 

Other studies showed that the glycosidic phosphate group of lipid A s is also substituted in Chromobacterium violaceum (by D-glucosamine, (22)), in Rhodospirilium tenue (by furanosidic D-arabinose, (30)) and, partially, in Escherichia coli (by phosphate, (36)). In a number of bacterial groups, however, the glycosidic phosphate appears to be unsubstituted (for literature see (8)). 

A similar distribution of fatty acids has also been detected in lipid A of other bacteria (Fig. 5). Thus, in Fusobacterium nucleatum, 2 moles of (R)-3-OH-14 0 are ester-bound, one of which is 3-O-acylated by 14 0. In amide linkage, (R)-3-0(14 0)-16 0 is present. In Vibrio cholerae, a dimer of (R)-3-OH-12 0 is bound as an ester while (R)-3-0-(14 0)-14 0 and (R)-3-0-(16 0)-14 0 are amide-linked. The lipid A component of Chromobacterium violaceum possesses 2 moles of (R)-3-OH-10 0 in ester linkage. The amide-bound acyl groups are represented by (R)-3-0H-12 0 residues which are 3-0-acylated by 12 0 and (S)-2-OH-12 0. In P. mirabilis, 3-0H-14 0 is, like in Salmonella, ester-and amide-bound. In this case, however, exclusively 14 0 substitutes the 3-hydroxyl groups of both 0- and N-linked 3-OH-14 0. 

Hoshino et al. described that in cultures of Chromobacterium violaceum, lycogalic acid (35, = chromopyrrolic acid) was derived from tryptophan [18]. It was therefore assumed that lycogalic acid (35) was formed by oxidative dimerization of 3-(indol-3-yl)pyruvic acid followed by reaction of the resulting 1,4-dicarbonyl intermediate with an equivalent of ammonia. On the basis of this idea, lycogarubin C (33) was synthesized from methyl 3-(indol-3-yl)pyruvate (37) in a simple one-pot process (Scheme 4). 

Chromobacterium violaceum is commonly found in soil and water and produces a purple pigment named violacein (Figure 32), which is water insoluble and has an antibacterial activity. Violacein production is regulated by Cvil—CviR quorum sensing system with C6-HSL in C. violaceum,316... 

Isatin serves as a substrate for the biosynthesis of violacein, a trypanocide agent, by Chromobacterium violaceum. ... 

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