The relation between natural and synthetical glycerylphosphoric acids. Pt. 2 / by Frank Tutin and A.C.O. Hann.

  • Tutin, Frank.
Date:
[1906]
Catalogue details

Licence: In copyright

Credit: The relation between natural and synthetical glycerylphosphoric acids. Pt. 2 / by Frank Tutin and A.C.O. Hann. Source: Wellcome Collection.

    3/14
    CLXX.—The Relation between Natural and Synthetical Glycerylphosphoric Acids. Part II. By Frank Tutin and Archie Cecil Osborn Hann. Willstatter, and Liidecke (Ber., 1904, 37, 3753) have described the preparation of some salts of a loevorotatory glycerylphosphoric acid obtained from egg-lecithin, from which they concluded that the natural glycerylphosphoric acid has the unsymmetrical configuration 0H*CH2*CH(0H)-CH2-0*P03H2. They also prepared the synthetical acid by heating together glycerol and phosphoric acid, and claimed to have found essential differences between the barium and calcium salts of the product thus obtained and the corresponding salts of the natural acid, not only with respect to solubility, but especially in the composition of the preparations when dried by heat (loc. cit.). In an account of an investigation by Dr. Power and one of us (Trans., 1905, 87, 249), it was shown that the above-mentioned differences in composition observed by Willstatter and Liidecke were due to the fact that their synthetical salts were not pure, but were contaminated with salts of the di-ester, C3H6(OH)<\q^>PO*OH. It was also stated that “the observation of Willstatter and Liidecke that the glycerylphosphoric acid from lecithin possessed optical activity, although certainly proving the presence of the unsymmetrical acid in the preparation, does not necessarily exclude the possibility that some of the symmetrical acid was also present.” Furthermore, that “ the same possibility naturally exists with respect to the homogeneity of the synthetical acid.” With the endeavour definitely to ascertain the nature of the natural and synthetical glycerylphosphoric acids, the present authors have 9h2-o-po»h2 synthesised the unsymmetrical, or a-acid, 0H*OH , and the sym- ch2-oh CEL-OH i * metrical, or /3-acid, CH*0*P03H2, and compared the barium and brucine CH2*OH salts of these compounds, on the one hand with the corresponding salts of the glycerylphosphoric acid prepared from glycerol and phosphoric acid * and, on the other, with those of the racemised acid from egg- lecithin.t * Subsequently referred to as the “ synthetical aoid.” t Subsequently referred^to as the “ natural acid.”