[24] Synthetic ketohexose phosphates: I. d-TAGATOSE-6-PHOSPHATE (cas 136377-13-4)

Add time:09/05/2019    Source:sciencedirect.com

Publisher SummaryThis chapter presents a procedure for the preparation of D-tagatose-6-phosphate, fructose-l-phosphate, L-sorbose-l-phosphate, and L-sorbose-6-phosphate. D-Tagatose can be converted to 1,2;3,4-diisopropylidene-D-tagatose by the procedure of Reichstein and Bosshard. The crystalline 1-diphenylphosphate-2,3;4,5-diisopropylidene-n-fructose (melting point 52.5 °) can be obtained by crystallization from a large volume of petroleum ether. Seed crystals may be obtained by taking up a small portion in hot petroleum ether, allowing it to cool, and decanting; after this procedure is repeated a few times, the compound crystallizes on scratching. For preparation of barium L-Sorbose-l-phosphate 2,3;4,6-diisopropylidene-L-sorbose-l-diphenyl phosphate is dissolved in redistilled methanol together with water and reduced in the presence of platinum oxide. It is cleaved by crystalline muscle aldolase to dihydroxyacetonephosphate and L-glyceraldehyde, although the cleavage can be detected only by employing an assay system which removes one of the products. For preparation of barium L-sorbose-6-phosphate the reduction of the tetraphenyl ester is carried out in glacial acetic acid or methanol with platinum oxide to catalyze the reaction. Deacetonation and hydrolytic removal of the 1-phosphate were achieved by dissolving the viscous material in water and heating on the steam bath. Further, the solution is precipitated and centrifuged to isolate barium L-sorbose-6-phosphate.

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