唾液酸的高碘酸盐-硫代巴比妥酸反应机制。
The mechanism of the periodate-thiobarbituric acid reaction of sialic acids.
作者信息
Paerels G B, Schut J
出版信息
Biochem J. 1965 Sep;96(3):787-92. doi: 10.1042/bj0960787.
Abstract
- The chromogen formation from N-acetylneuraminic acid in the periodate-thiobarbituric acid reaction was investigated. Measurement of periodate consumption showed an uptake of approx. 3moles/mole of substrate in neutral as well as in strongly acidic solution. Therefore the chromogen beta-formylpyruvic acid is not a direct product of the periodate oxidation; it is presumed to be formed from the true oxidation product, a hexos-5-uluronic acid, by aldol splitting during the reaction in hot acidic solution with thiobarbituric acid. 2. Methyl (methyl beta-l-threo-hexos-4-enepyranosid)uronate, an analogue of the pre-chromogen, has been shown to yield with thiobarbituric acid in acidic solution a pigment exhibiting an identical absorption spectrum and showing the same behaviour on paper chromatography as the pigment obtained from N-acetylneuraminic acid in the periodate-thiobarbituric acid assay. 3. The substitution at C-2 of methoxyneuraminic acid does not inhibit the periodate-thiobarbituric acid reaction. In neutral solution methoxyneuraminic acid is oxidized by periodate to a substance that reacts readily with thiobarbituric acid in acidic solution. When periodate oxidation is attempted in acidic solution, protonation of the amino group protects this group against oxidation, rendering methoxyneuraminic acid negative in the assay systems of Warren (1959a,b) and Aminoff (1959, 1961).
摘要
- 研究了在高碘酸盐 - 硫代巴比妥酸反应中由N - 乙酰神经氨酸形成色原的过程。高碘酸盐消耗量的测量表明，在中性以及强酸性溶液中，每摩尔底物大约摄取3摩尔高碘酸盐。因此，色原β - 甲酰丙酮酸不是高碘酸盐氧化的直接产物；据推测，它是由真正的氧化产物己糖 - 5 - 醛糖醛酸在热酸性溶液中与硫代巴比妥酸反应时通过羟醛裂解形成的。2. 甲基（甲基β - l - 苏式 - 己糖 - 4 - 烯吡喃糖苷）uronate，一种前色原的类似物，已被证明在酸性溶液中与硫代巴比妥酸反应生成一种色素，该色素具有相同的吸收光谱，并且在纸上色谱分析中的行为与在高碘酸盐 - 硫代巴比妥酸测定中从N - 乙酰神经氨酸获得的色素相同。3. 甲氧基神经氨酸在C - 2处的取代并不抑制高碘酸盐 - 硫代巴比妥酸反应。在中性溶液中，甲氧基神经氨酸被高碘酸盐氧化为一种在酸性溶液中能与硫代巴比妥酸迅速反应的物质。当尝试在酸性溶液中进行高碘酸盐氧化时，氨基的质子化保护该基团不被氧化，使得甲氧基神经氨酸在沃伦（1959a，b）和阿米诺夫（1959，1961）的测定系统中呈阴性。
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