Corrinoid compounds

Corrin and octadehydrocorrin represent the extremes in the family of corrinoid compounds between these two structures there are those macrocycles in which additional double bonds can be systematically introduced in the ring. 

Kittaka-Katsura, H. Fujita, T. Watanahe, F. Nakano, Y. Purification and characterization of a corrinoid compound from Chlorella tablets as an algal health food. J. Agric. Food Chem. 2002, 50 (17), 4994-4997. 

Phthalocyanities and Related Compounds 3.2 Porphinoid and Corrinoid Compounds... 

Watanabe, R, Michihata, T., Takenaka, S., Kittaka-Katsura, H., Enomoto, T., Miyamoto, E., and Adachi, S. Purification and characterization of corrinoid compounds from a Japanese fish sauce. J. Liquid Chromatogr. Related Technol. 27, 2113 (2004). 

A similar system of nomenclature will be used as in the earlier article. Approaches to the further systematization of trivial names have been reviewed elsewhere, and the numbering system of the International Union of Pure and Applied Chemistry (lUPAC) is slowly gaining ground. The Fischer system is used where necessary in this article in referring to porphyrins to preserve continuity with the earlier article and with the enormous volume of the earlier literature on porphyrins however, the lUPAC systemwill be used as before for vitamin Bi2 and corrinoid compounds because of its clear advantages in this field. 

Synthesis of Macrocyclic and Linear Tetrapyrrole Compounds Corrinoid Compounds in Edible Cyanobacteria... 

Spirulina tablets contain large amounts (127-244 pg/100 g weight) of B12 when assayed using microbiological method [28]. However, Herbert and Drivas [29] showed that most B12 found in Spirulina tablets comprise biologically inactive corrinoid compounds. Several studies [30,31] also indicate that these Spirulina corrinoids may not be bioavailable in manunals. To clarify whether Spirulina tablets contain active B12 or inactive corrinoid compounds, two corrinoid compounds (major, 83% and minor, 17%) were purified and then identified as pseudo-Bi2 and B12, respectively [30] (Fig. 1). 

A. flos-aquae grows naturally in Upper Klamath Lake, OR, USA. This cyanobacterium contains various nutrients including polyunsaturated fatty acids, protein, carotenoids, vitamins, and minerals and have therapeutic effects [32]. Dried Aphanizomenon cells contained 616 pg of B12 per 100 g when assayed using microbiological method [33]. However, the corrinoid compound purified from these dried cells was identified as pseudo-Bi2 [33]. 

Dried N. commune also contained considerable quantities (99 pg/100 g dry weight) of Bi2 when assayed with the microbiological method [35]. Two corrinoid compounds (major, 88% and minor, 12%) purified from this cyanobacterium were identified as pseudo-Bi2 and B12, respectively [35]. 

Substantial quantities of edible cyanobacteria are produced globally to meet the high demands of both food and pharmaceutical industries. These cyanobacteria contain substantial quantities of phycobiliproteins, of which phycocy-anin, in particular, has various therapeutic effects owing to the linear tetrapyrrole chromophore phycocyanobilin. Cyanobacteria can also synthesize macrocyclic tetrapyrrole corrinoid compounds. However, various edible cyanobacteria contain substantial quantities of inactive pseudo-Bi2 rather than active Bi2- To overcome this nutritional defect of edible cyanobacteria, it is vital to determine the genetic, biochemical, and physiological properties of pseudo-Bi2-... 

Watanabe, F. Katsura, H. Takenaka, S. Fujita, T. Abe, K. Tamura, Y. Nakatsuka, T. Nakano, Y. PseudovitaminBi2is the predominant cobamide of an algal health food, Spindina tablets. J. Agric. Food Chem. 1999,47 (11), 4736 741. Kittaka-Katsura, H. Fujita, T. Watanabe, F. Nakano, Y. Purification and characterization of a corrinoid compound from Chlorella tablets as an algal health food. J. Agric. Food Chem. 2002,50 (17), 4994-A997. 

Miyamoto, E. Watanabe, F. Ebara, S. Takenaka, S. Takenaka, H. Yamaguchi, Y. Tanaka, N. Inui, H. Nakano, Y. Characterization of a vitamin B12 compound from unicellular coccolithophorid alga iPleurochrysis car-terae). J. Agric. Food Chem. 2001, 49 (7), 3486-3489. Takenaka, S. Enomoto, T. Tsuyama, S. Watanabe, F. TLC analysis of corrinoid compounds in fish sauce. J. Liq. Chromatogr. Relat. Technol. 2003, 26 (16), 2703-2707. 

Emi, M., Yuri, T., Tomoyuki, N., Florin, B., Hiroshi, I., Tomoyuki, F., Watanabe, F., and Yoshihisa, N., 2006. Purification and characterization of a corrinoid-compound in an edible cyanobacterium Aphanizomenonfios-aquae as a nutritional supplementary food. Journal of Agriculture Food Chemistry. 54 9604-9607. 

Barker HA (1967) Biochemical functions of corrinoid compounds. Biochem J 105 1-15 Barker HA and Lipmann F (1944) On lactic acid metabohsm in propionic acid bacteria and the problem of oxido-reduction in the system of fatty-hydroxyketo acids. Arch Biochem 4 361-370... 

V. Further Transmethylations From Methyl-Cobalt—Corrinoid Compounds... 

The synthesis of methionine, the formation of methane, and the formation of acetate furnish examples of the capacity of Co-corrinoid compounds to act as carriers in methyl transfer reactions. At the present time it is difficult to judge whether this chemical capability of the Co-corrinoid compounds has been utilized more widely in nature for other transmethylation reactions. It has recently been reported that CHs-cobalamin can serve as a methyl donor in the formation of methylated bases in transfer RNA. Although a significant rate of nonenzymic reaction occurred, enzymes from both rat liver and the bacterium Propionibacterium shermanii increased die rate of methylation (Walerych et al., 1966). When extracts of a methane-forming bacterium were incubated with CHa-Bi2 and mer-... 

The clarification of the structure of coenzyme B g stimulated attempts to synthesize the compound from vitamin B g and an activated adenosine derivative. Smith et described a chemical synthesis of the coentyme from fully reduced vitamin Big (Bi and the 5 -tosyl-2, 3 -isopropylidene derivative of adenosine. At the same time they reported the synthesis of Co-methyl-cobalamin from Bigg and methyl iodide. Soon thereafter a biological function of methylcobalamin in the methylation of homo steine was demonstrated by Guest et Only one other Co-alkyl-corrinoid compound has so far been... 

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