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| | 5'-Deoxyadenosylcobalamin Basic information |
| | 5'-Deoxyadenosylcobalamin Chemical Properties |
| storage temp. | -20°C | | solubility | DMSO (Slightly), Methanol (Slightly), Water (Slightly, Sonicated) | | form | Solid | | pka | 3.5(at 25℃) | | color | Red to Very Dark Red | | Water Solubility | 26g/L(24 ºC) | | Merck | 13,2476 | | BRN | 4122932 | | Stability: | Hygroscopic |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 22-24/25-36-26 | | WGK Germany | 3 | | RTECS | GG3800000 | | F | 8 | | HS Code | 2936260000 | | Toxicity | LD50 oral in guinea pig: 5gm/kg |
| | 5'-Deoxyadenosylcobalamin Usage And Synthesis |
| Originator | Actimide,Tobishi | | Uses | emulsifying agent | | Uses | Coenzyme B12 has been used as a supplement for culturing plasmid variants in in vivo assay of yvrC-lacZ fusions. | | Definition | ChEBI: A member of the class of cobalamins that is vitamin B12 in which the cyano group is replaced by a 5'-deoxyadenos-5'-yl moiety. It is one of the two metabolically active form of vitamin B12. | | Manufacturing Process | Isopropylidine adenosine was converted to the p-toluene sulphonyl (tosyl)
ester by reaction with tosyl chlorine solution, following the method of Clark et
al. (1951) [J. Chem. Soc. 2952]. Because of its tendency to cyclization, the
reagent was used directly it was ready. A reaction flask with separating
funnels was set up in such a way that the whole system could be evacuated
and filled with pure nitrogen two or three times, to eliminate all oxygen, and
reagents could then be added when desired, in the closed system.
The flask contained 700.0 mg hydroxocobalamin in 20 ml of water, one funnel
200.0 mg sodium borohydride in 10 ml of water, and another the crude
isopropylidine adenosine tosyl ester made from 500 mg isopropylidine
adenosine dissolved in 10 ml of 50% aqueous methanol. On adding the
borohydride to the vitamin, the color changed instantly from red to brown,
then slowly to a greenish black. After 15 min the isopropylidine adenosine
tosyl ester was added, and the colour slowly changed to a red-brown. After 45
min at room temperature air was admitted and the mixture was shaken to
reoxidise any remaining reduced vitamin B12. The alkaline solution was
neutralized with dilute hydrochloric acid and extracted with phenol carbon
tetrachloride 3:1 in small portions till the aqueous layer was nearly colorless.
The combined extracts were washed with water, mixed with about ten parts of
carbon tetrachloride-acetone 10:1 and shaken with small portions of water till
all red color was removed.
The product was purified by chromatography on columns of DEAE (diethyl
aminoethyl) cellulose (3 x 1) followed by CM (carboxymethyl) cellulose (6 x
1), developed with water. Nearly all the color washed quickly through DEAE
cellulose. The effluent and washes were applied to the CM cellulose column,
which was further developed with water. Elution was continued as long as this
fraction continued to emerge, in a total of 850 ml. One half of this fraction
(425 ml) was concentrated to a few ml under reduced pressure; it crystallized
slowly after adding acetone to slight turbidity. So cobamamide was obtained. | | Therapeutic Function | Anabolic, Analgesic | | General Description | Vitamin B12 cobalamin refers to a group of chemically-related cobalt containing molecules. The physiologically active forms of vitamin B12 include methylcobalamin and adenosylcobalamin, whereas hydroxocobalamin (vitamin B12a, OHCbl) and cyanocobalamin (CNCbl) are storage and delivery forms. | | Agricultural Uses | Cobamide enzyme is the cobalt complex formed between the cobalt-porphyrin ring structure and the nucleotide in vitamin B12 co-enzyme. | | Biochem/physiol Actions | Vitamin B12 cobalamin is involved in DNA synthesis and fatty acid synthesis. It also plays a vital role as a coenzyme in the conversion of mitochondrial methylmalonyl co-enzyme A to succinyl co-enzyme A. |
| | 5'-Deoxyadenosylcobalamin Preparation Products And Raw materials |
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