Preparation of double sulfate salt of desoxyfructosyl serotonin

Details Preparation of double sulfate salt of desoxyfructosyl serotonin Preparation of double sulfate salt of desoxyfructosyl serotonin

1987-11-13

1990-05-15

Griffin, Ronald W.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 55, C08B 3700, C07H 504

Patent

active

049259326

ABSTRACT:
A double sulfate salt of 1-desoxy-(5-hydroxytryptamino)-D-fructose (DFS) and 1-methylhydantoin-2-imide (creatinine) is prepared by adding creatinine to an aqueous solution of DFS containing sulfuric acid having a pH of approximately 3. The double salt may be isolated by crystallizing it in the presence of a water-miscible solvent such as ethanol. DFS may be prepared by glycosylation of 5-hydroxytryptamine with D-glucose and then adding an excess of calcium hydroxide to the glycosylation reaction medium for precipitating DFS.CA(OH).sub.2 from which the DFS may be isolated for preparing the double salt as described above. Recycling and treatment of mother liquors enables yields to be increased.

REFERENCES:
J. E. Hodge et al., "Amadori Rearrangement Products", Methods in Carbohydrate Chemistry, vol. II, 1963 pp. 99-107.
P. Jayaraman, et al, "Inhibition of the Incorporation of [.sup.3 H] DOPA in Mycobacterium Leptae by Desoxyfructo-Serotonian", Biochemical Pharmacology vol. 29, 1980, pp. 2526-2528.

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