Method of synthesis of β-thiolato cobalamin compounds

Details Method of synthesis of β-thiolato cobalamin compounds Method of synthesis of β-thiolato cobalamin compounds

2006-04-18

2006-04-18

Wilson, James O. (Department: 1623)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C424S009362, C424S009610, C540S145000, C534S015000, C514S410000

Reexamination Certificate

active

07030105

ABSTRACT:
The invention provides a method for preparing glutathionylcobalamin (GluSCbl) which involves running the reaction in an aqueous solvent with a relatively small excess of glutathione, i.e. GluSH, specifically from one to less than four molar equivalents of GluSH. The formed GluSCbl is precipitated from the aqueous solvent, preferably by the addition of a precipitate inducing solvent. This provides GluSCbl in acceptable purity without the need for an additional chromatographic purification step. Additionally, it has been found that the reaction can be run to an acceptable level of purity by using very high concentrations of the reactants, i.e. around saturation concentrations for aquocobalamin. This has the advantage of eliminating the need for air-free conditions.

REFERENCES:
patent: 3146165 (1964-08-01), Heathcote
Shargel et al. Comprehensive Pharmacy Review. 4th Edition.Lippincott Williams & Wilkins. 2001. pp. 54-57, 99-100.
Gennaro et al. Remington: The Science and Practice of Pharmacy. 19th edition. Philadelphia College of Pharmacy and Science. 1995. pp. 631-634.
Article fromJournal of the American Chemical Society/88:21/Nov. 5, 1966, pp. 5018-5019, entitled Reaction of Hydroxocobalamin with Thiols; Norman Adler, Thomas Medwick, and T. J. Poznanski.
Vol. 169, No. 2, 1990, Jun. 2, 1990; pp. 443-450;Biochemical and Biophysical Research Communications; Ewa Pezacka, Ralph Green and Donald W. Jacobsen.
Article Biochemistry 1993, 32, 8421-8428;Heteronuclear Nuclear Magnetic Resonance Studies of Cobalt Corrinoids. 15. The Structure of Glutathionylcobalamin: A1H and13C Two-Dimensional Nuclear Magnetic Resonance Study at 600 MHz†Kenneth L. Brown and Xiang Zou; Department of Chemistry, Box CH, Mississippi State University, Mississippi State, Mississippi 39762; Susan R. Sabon and Donald W. Jacobsen; Department of Cell Biology and Clinical Pathology, The Cleveland Clinic Foundation , Cleveland, OH 44106; Received Mar. 12, 1993; Revised Manuscript Received May 6, 1993.
Article fromJournal of Inorganic Biochemistry76 (1999) 197-209pp. 197-209; entitled “Synthesis and characterization of isolable thiolatocobalamin complexes relevant to coenzyme B12-dependent ribonucleoside triphosphate reductase” Nicola E. Brasch, Twui-Ling Carolyn Hsu, Kenneth M. Doll, Richard G. Finke, Department of Chemistry, Colorado State University, Fort Collins, CO 80523; Received Mar. 5, 1999; received in revised form Aug. 2, 1999; accepted Aug. 16, 1999.
Inorganic Chemistryvol. 40, No. 12, 2001; pp. 2686-2692; “Synthesis, Characterization, Solution Stability, and X-ray Crystal Structure of the Thiolatocobalamin γ-Glutamylcysteinylcobalamin, a Dipeptide Analogue of Glutamylcysteinylcobalamin: Insights into the Enhanced Co—S Bond Stability of the Natural Product Glutamylcysteinylcobalamin”; Robert K. Suto,†Nicola E. Brasch,‡,§Oren P. Anderson,‡and Richard G. Finke*,‡Departments of Biochemistry and Chemistry, Colorado State University, Fort Collins, CO 80523; Received Dec. 6, 2000.

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