5'-Deoxyadenosylcobalamin，COENZYME B12

Details:

5'-Deoxyadenosylcobalamin Chemical Properties
storage temp.     -20°C
solubility     DMSO (Slightly), Methanol (Slightly), Water (Slightly, Sonicated)
pka    3.5(at 25℃)
form     Solid
color     Red to Very Dark Red
Water Solubility     26g/L(24 ºC)
Merck     13,2476
BRN     4122932
Stability:    Hygroscopic
Safety Information
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
MSDS Information
Provider    Language
SigmaAldrich    English
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.