The Unidentified Base in Gelatin

Slyke, Donald D. Van; Hiller, Alma; Dillon, Robert T.; MacFadyen, Douglas A.

doi:10.3181/00379727-38-9929p

Cited by 39 publications

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“…There seems little doubt, however, when the results of the periodate oxidation are considered in conjunction with the other properties of the picrate isolated from these mother liquors, that the base in question was hydroxylysine. The claims of Van Slyke et al (1938) are thus confirmed.…”

Section: Experimental Main Picrate Fractionmentioning

confidence: 54%

“…Martin & Synge (1941), by the application of an acetylation-benzoylation procedure to the lysine ,fractions of gelatin and isinglass hydrolysates, isolated in each case a small amount of a crystalline picrate which exploded at 226-227°. Although their analytical figures for formaldehyde and ammonia evolved on periodate treatment were low, this work is the only independent confirmation, by isolation, of the existence of the base first described by Van Slyke et al (1938).…”

mentioning

confidence: 50%

“…UsingVorlander's (1929) technique for determining the formaldehyde produced by oxidation of the 'lysine fraction' of isinglass, Beveridge & Lucas (1944) obtained a value from which they deduced the probable presence of some 0-36 % hydroxylysine. It was not apparent whether the compound estimated was that described by Schryver et al (1925), or by Van Slyke et al (1938), and accordingly they attempted the isolation advocated by the American workers, but failed to obtain any hydroxylysine picrate. More recently, Rees (1946) has carried out estimations by periodate oxidation which have confirmed the presence of a basic hydroxy amino-acid in gelatin and collagen, but not in any other proteins examined.…”

mentioning

confidence: 99%

“…Itwasconfirmedthatbarium (Wieland& Rosenthal, 1943) and bicarbonate (Breusch, 1943 a, b) Schryver, Buston & Mukherjee (1925) claimed the isolation, from isinglass hydrolysate, of an 'oxylysine' to which they attributed the formula C,H1403N2; but they were unable, on repeated attempts, to prepare a crystalline picrate. Van Slyke & Hiller (1921) reported the presence of hitherto unknown material in the basic amino-acid fraction ofhydrolyzed gelatin; this base was isolated by Van Slyke, Hiller, Dillon & MacFadyen (1938) who ascribed to it the fQrmula of a hydroxylysine.…”

mentioning

confidence: 99%

“…6CH307N3, which melted at 2250 when heated slowly, was eventually isolated from the mother liquor. Van Slyke, Hiller, MacFadyen, Hastings & Klemperer (1940) and Van Slyke, Hiller & MacFadyen (1941) have since endeavoured to establish the structure of hydroxylysine, and to determine its presence in other proteins by adaptation of the periodate oxidation reaction of Nicolet & Shinn (1939). Martin & Synge (1941), by the application of an acetylation-benzoylation procedure to the lysine ,fractions of gelatin and isinglass hydrolysates, isolated in each case a small amount of a crystalline picrate which exploded at 226-227°.…”

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confidence: 99%

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The isolation of hydroxylysine picrate from a gelatin hydrolysate

Heathcote

1948

Biochemical Journal

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Vol. 42 ACETOACETATE METABOLISM. 2 305 L-malate, citrate, a-ketoglutarate) found in solutions as a result of the interaction between acetoacetate and oxaloacetate were determined in aerobic and anaerobic experiments. The most notable effect of oxygen on the yields of various substances was a higher yield of citrate. Calculations based on the yields suggest that acetoacetate contributes towards the formation of the acids of the tricarboxylic cycle, a conclusion now firmly established by the tracer work of Buchanan et al. and of Weinhouse et al.5. Erythro-1:2-dihydroxybutyric acid was not metabolized by sheep kidney cortex whilst the threo form was slowly oxidized. In accordance with Weil-Malherbe's findings, the slowness of the oxidation exclude § this substance as an intermediate in the removal of ketone bodies.6. Measurements of the rates of ac-ketoglutarate formation from various substrates and substrate combinations showed that the tricarboxylic acids yield a-ketoglutarate more rapidly than any other substrate. This supports the assumption that oc-ketoglutarate arises via the tricarboxylic acids when formed in the presence of oxaloacetate and acetoacetate (or pyruvate). The rate of citrate formation via carboxylation of oc-ketoglutarate (Ochoa, 1945) was relatively slow in sheep kidney cortex.7. The sum of ci8aconitate plus iwocitrate was found to exceed 10-5% of the total tricarboxylic acids (maximum 49 %) under suitable conditions. It is pointed out that this finding excludes the sequence (4) (p. 302) and supports the sequence (3) (p. 301), confirming conclusions earlier drawn from tracer work.8. Itwasconfirmedthatbarium (Wieland& Rosenthal, 1943) and bicarbonate (Breusch, 1943 a, b) ions increase the yield of citrate from oxaloacetate and acetoacetate. Possible causes of this effect were investigated.

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Section: Experimental Main Picrate Fractionmentioning

confidence: 54%

mentioning

confidence: 50%

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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The isolation of hydroxylysine picrate from a gelatin hydrolysate

Heathcote

1948

Biochemical Journal

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Stereoselective Synthesis of (2R,5R)- and (2S,5R)-5-Hydroxylysine

et al. 2000

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Collagens and Gelatins

2003

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Introduction Historical Outline Early Background The Golden Age of Collagen Discoveries: Composition, Conformation, and Fibril Organization Amino Acid Sequence, Genetic Diversity, and Precursors Chemical Structure Unusual Amino Acid Features and Post‐translational Modifications Cross‐links Between Collagen Chains Structure of the Collagen Triple Helix Occurrence and Function of Collagen Fibril‐forming Collagens Non‐fibrillar Collagens Biosynthesis and Biochemistry of Collagen Physiology Biodegradation Polypeptide Models of Collagen Molecular Genetics and Collagen Diseases Chemical Analysis and Detection Production and Applications Biomedical Applications of Collagen Gelatin Production and Applications Recombinant Collagen and Gelatin Immunological Response to Collagen Products Patents Outlook and Perspectives Acknowledgements

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The Unidentified Base in Gelatin

Cited by 39 publications

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The isolation of hydroxylysine picrate from a gelatin hydrolysate

The isolation of hydroxylysine picrate from a gelatin hydrolysate

Stereoselective Synthesis of (2R,5R)- and (2S,5R)-5-Hydroxylysine

Collagens and Gelatins

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