Biographical Memoirs Volume 51 (1980) / Chapter Skim
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Walter Abraham Jacobs
Walter Abraham Jacobs
Pages 246-279
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with the latter's work on the chemistry of the nucleic acids. The studies, first with the nucleotide inosinic acid from beef extract, clisclosed its essential chemistry by hydrolysis to the nucleosicle, inosine, and by subsequent cleavage from the latter of its crystalline sugar component which was iclentified 247
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In collaboration with Michael Heidelberger, he began an investigation of the possible chemotherapy of polio. It was known that hexamethylenetetramine apparently exerted a slight therapeutic effect, and an extended series of quaternary salts was prepared by reaction with aromatic and alipathic halogen compounds.
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Several patents were awarded for control of the drug and several of its analogs—although none of the latter proved to be superior to Tryparsamide. At the conclusion of World War I, Louise Pearce made an extensive study of the drug in the Belgian Congo; which showed Tryparsamicle- to be more effective than previously used drugs.
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was due to the sufanilamicle liberated on metabolism of Prontosil. It apparently never occurred to Jacobs and Heidelberger in ~ 920 that such a simple substance could control bacterial infections by other than direct antibacterial action.
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At the time Jacobs began his investigations on the structures of these important compounds, little was known of them or their chemistry. It was known that they were glycosides consisting of a rather complicated aglycone moiety, which was responsible for their major pharmacological properties, joiner!
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With the aid of X-ray data, the latter basic ring system was shown to be that of the Diels' hydrocarbon, a perhydrocyclopentanophenanthrene, by British workers. The problem of the location of the unsaturated lactone side chain on the nucleus of the aglycones was resolved by application of the Barbier-Wieland degradation, used successfully in degradation of the sicle chain of cholanic acid, to a derivative of (ligitoxigenin with the formation of etiocholanic acid as the final product.
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a sigh of relief. With one minor revision, involving the position of the double bond in the unsaturated lactone side chain, the structure of the cardiac aglycones was established.
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The plant heart drugs also display this property, but are classified separately because of their distinctive physiological heart action. Early emphasis was placed on the readily available sarsasapogenin from Smiler ornata Hooker.
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{ysergic acid, which proved to be the characteristic building block of the ergot alkaloids, was isolated. The other products of hyclrolysis of the alkaloids were amino acid (derivatives joined by pepticle linkages to themselves and to lysergic acid.
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The final group of natural products to which Jacobs turned his attention embraces a complex family now known as the steroid bases, or veratrum alkaloids, found in various Veratrum species. These fall into two classes, as suggested by Fieser and Fieser*
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The investigations of Jacobs on the veratrum alkaloids continued for some twenty years until his retirement, and formed the basis for more extensive studies of these structurally very complicated molecules by other workers. Walter Jacobs was a very highly regarcled member of the Rockefeller Institute for some fifty years.
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Walter, fir. He was granted emeritus status at the Rockefeller in ~ 949, but continued active laboratory work until 1957, when he retired and migrated to Los Angeles.
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WALTER ABRAHAM JACOBS HONORS AND DISTINCTIONS AWARDS Belgian Order of Leopold II, 1953 PROFESSIONAL AND HONORARY SOCIETIES 259 National Academy of Sciences (elected, 1932) American Association for the Advancement of Science American Chemical Society American Society of Biological Chemists American Society of Pharmacology and Experimental Therapeutics Harvey Society
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Spaltung des racemischen Serins in die optischaktiven Componenten. Ber, Dtsch.
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Guaninehexoside obtained on hydrolysis of thymus nucleic acid.
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VIII. Miscellaneous substances containing aliphatically bound halogen and the hexamethylenetetraminium salts derived therefrom.
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III. The relation between constitution and bactericidal action in the quaternary salts obtained from halogenacetyl compounds.
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Sodium salts of organic arsenic compounds.
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VI. Aminoazo and hydroxyazo dyes derived from certain 5-amino cinchona alkaloids and their quinoline analogs.
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III. Crystalline Kombe strophanthin.
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L Gustus The association of the double bond with the lactone group in the cardiac aglucones.
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The hydrogenation of unsaturated lactones to desoxy acids.
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The hydrogenation of unsaturated lactones to desoxy acids.
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Lysergic acid.
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The ultraviolet absorption spectra of lysergic acid and related substances. Science, 83:16~67.
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XIV. The positions of the double bond and the carboxyl group in lysergic acid and its isomer.
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XVIII. The production of a base from lysergic acid and its comparison with synthetic 6,8-dimethylergoline.
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XIX. The transformation of dl-lysergic acid and d-lysergic acid to 6,8-dimethylergolines.
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Phoebus Aaron Theodor Levene. In: Biographical Memoirs, 23:7~126.
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XIX. Further studies with delphinine derivatives.
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XXXIX. A study of certain selenium dehydrogenation products of cevine.
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XXXV. Structural studies with delphinine derivatives.
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