The synthesis of histidine / by Frank Lee Pyman.

  • Pyman, Frank Lee.
Date:
[between 1900 and 1909?]
Catalogue details

Licence: In copyright

Credit: The synthesis of histidine / by Frank Lee Pyman. Source: Wellcome Collection.

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    CLVII.—The Synthesis of Histidine. By Frank Lee Pyman. In the following paper an account is given of the synthesis of histidine (Z-a-amino-/3-glyoxaline-4(or 5)-propionic acid), and it may be of interest, in the first place, to recall that this amino^acid is JT|^>0-CH2-CH(NH2)-C02H, Histidine. a compound of considerable biochemical importance, since it occurs as a degradation product of nearly all albumins, and notably in large amount by the hydrolysis of haemoglobin. It was first dis¬ covered by Kossel (Zeitsch. 'physiol. Ghem., 1896, 22, 176), and its constitution was determined mainly by the work of Frankel (Monatsh., 1903, 24, 229), Paul (Zeitsch. physiol. Ghem., 1904, 42, 513), and Knoop and Wfndaus (Beitr. chem. Physiol. Path., 1905, 7, 144). In a recent communication (this vol., p. 668) the preparation of certain glyoxaline derivatives was described. It was shown that 4(5r 5)-chloromethylglyoxaline (I) is a highly reactive compound, the chlorine atom in the side-chain being readily replaced by hydroxyl under the influence of hot water, and by the cyano-group through the agency of aqueous potassium cyanide at 0°. It therefore seemed probable that this salt could be condensed with compounds of the type of ethyl sodiomalonate, forming the corresponding glyoxalinemethyl, CgHgNyCH^’, derivatives, and this proved to be the case. On adding one molecule of this salt to two molecules of ethyl sodiomalonate, ethyl 4(or 5yglyoxalinemethylmalonate