Chromobacterium

Lipase-catalyzed intermolecular condensation of diacids with diols results in a mixture of macrocycUc lactones and liuear oligomers. Interestingly, the reaction temperature has a strong effect on the product distribution. The condensation of a,(D-diacids with a,(D-dialcohols catalyzed by Candida glindracea or Pseudomonas sp. Upases leads to macrocycUc lactones at temperatures between 55 and 75°C (91), but at lower temperatures (<45°C) the formation of oligomeric esters predorninates. Optically active trimers and pentamers can be produced at room temperature by PPL or Chromobacterium viscosum Upase-catalyzed condensation of bis (2,2,2-trichloroethyl) (+)-3-meth5ladipate and 1,6-hexanediol (92). 

Reference has already been made to iodinin (120) (1,6-dihydroxyphenazine 5,10-dioxide), the violet pigment produced by the bacterium Chromobacterium iodinium. Iodinin... 

Chromobacterium viscosum lipase, cyclohexane, vinyl acetate, THF, 40°." Cleavage... 

Under comparable conditions, the reaction rates of the octyl decanoate synthesis by chromobacterium viscosum lipase in AOT-based microemulsions or immobihzed in AOT-based organogels were similar [286,287],... 

In turn, a lipase-promoted acylahon of prochiral substrates 104, using lipases from Candida cylinracea and Chromobacterium viscosum and methyl isobutyrate or acetoxime isobutyrate as the acyl donors, gave the product 105 in yields up to 80% and with ees up to 75% (Equahon 50). ... 

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. 

Isolation of lipase A from lipase B from crude Chromobacterium viscosum extract [80,81]... 

Lipase from Chromobacterium viscosum Esterification of 1-butanol and oleic acid Oil-deionized water (96.6/3.4) 14.2 103... 

Lipase from Chromobacterium viscosum Transesterification of 2-ethyl-l-hexanol and rapeseed oil Oil-water (97/3) 97.2 103... 

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. 

Specific Polysaccharide of some Strains of Chromobacterium vioiaceum. Biochem. J. 64, 22 P (1956). 

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.

Ueda H, Nakajima H, Hori Y, Fujita T, Nishimura M, Goto T, Okuhara M. (1994) FR901228, a novel antitumor bicycUc depsipeptide produced by chromobacterium. J Antibiot 47 301-310. 

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. 

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