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Extra resources for Advances in Carbohydrate Chemistry, Vol. 5

Sample text

111. Synthesis of Sucrose through the Mechanism of Phosphorolysis.. . . . . IV. Specificity of Sucrose Phospliorylase. . . . . . . . . . . . . . . . . V. Synthetic Non-reducing Disnccharides . . . . . . . . . . . . . . . . 1. Synthetic Sucrose.. . . . . . . . . . . . . . . . . . . . . . a. Preparation of the Enzymatic Extract from Pseudomonas saccharophila . . . . . . . . . . . . b. Enzymatic Synthesis and Isolation of Synthetic Sucrose.

This extract contains a considerable amount of invertase and a small amount of phosphatase. Subsequent treatment of the extract with ammonium sulfate32gave rise to preparations which contained from a third to a half of the original phosphorylase but very little invertase or phosphatase. 6 saturation were made throughout a period of two or three days, during which the preparation was stored in the refrigerator. Any denatured, insoluble proteins were removed by centrifugation, and a solution of the desired activity was prepared by dilution with buffer or distilled water.

Maehly and T. Reichstein, Helv. Chim. Acta, 30, 496 (1947). DESULFURIZATION BY RANEY NICKEL 21 prepared from a four-fold quantity of Raney alloy (approximately 50% nickel) caused only desulfurization and gave methyl 2-desoxy-4,6benzylidene-a-D-guloside (LXVIII) in 57 % yield. When the Raney nickel prepared from a thirty-fold quantity of alloy was used the benzylidene group also was removed and the product was methyl 2-desoxya-D-guloside (LXIX). Other idose derivatives were hydrogenated by H & F I HA- HCO-- c: H 0 LXIV LXV H OCHa H CHIS H I G AHZ I I I LOkHz LXVIII C H s O F HobH b H SCHs + - 0 b H Gut, Prins and Reichstein:62 methyl 3-methylthio-4,6-benzylidene-@-~idoside (LXX) with a four-fold quantity of Raney nickel (prepared from an eight-fold quantity of alloy) gave methyl 3-desoxy-4,6-benzylidene-fl-D-idoside (LXXI) in 92% yield; use of a large excess of nickel resulted in simultaneous debenzylidenation.

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