Advances in Carbohydrate Chemistry, Vol. 5 by Claude S. Hudson, etc.

By Claude S. Hudson, etc.

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A quantitative estimation of the synthetic sucrose carried out with the aid of yeast invertase indicated that approximately 3 g. of this sugar had been formed in this reaction. 5 volumes of 95% alcohol added. The mixture was allowed to remain at 4" for 3 hours and the precipitate, containing most of the inorganic and esterified phosphate, was removed by filtration and the alcohol was removed by distillation in VUCUO at about 30". The solution was then made up to 600 ml. and passed through columns of Amberlite IR-100 and Amberlite I R 4 .

148, 67 (1943). 34 W. Z. HASSID AND M. DOUDOROFF D-glucose-1-phosphate and D-fructose, Hassid, Doudoroff and Barker’? succeeded in crystallizing a non-reducing disaccharide which was indistinguishable from natural sucrose. It was thus that the first laboratory synthesis of sucrose was achieved. The formation of Pglucose-1-phosphate and D-fructose from sucrose and inorganic phosphate, similar to the phosphorolysis of starch21 and glycogen,22may be considered to occur as the result of phosphorolytic cleavage of D-glucose from the sucrose molecule, the sucrose being disrupted without water entering into the reaction.

60, 1537 (1938). (41) R. M. Hann and C. 8. Hudson, J . Am. Chem. , 66, 735 (1944); W. T. H a s h , R. M. Ham, and C. S. , 87, 939 (1945). W. 2. RASSID AND M. DOUDOROFF 44 formic acid, with no formaldehyde production; the experimental data exclude the possibility of this union a t carbon atom 4. Junction of D-glucopyranose to carbon atom 5 of the L-arabinose phenylosotriazole would require three moles of periodate whereby one mole of formic acid would be produced, and no formaldehyde formed; these expectations likewise disagree with the experimental data and in consequence a union at carbon atom 5 is excluded, and there remains only the possibility of a union at carbon atom 3 as shown in the formula VI.

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