Purification and structural characterization of 3-hydroxypropionaldehyde and its derivatives
Purification and structural characterization of 3-hydroxypropionaldehyde and its derivatives
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DOI：
10.1021/jf021086d
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发表时间：
2003-05-21
影响因子：
6.1
通讯作者：
Puhan, Z
中科院分区：
文献类型：
--
作者：
Vollenweider, S;Grassi, G;Puhan, Z
化合物3-羟基丙醛（3-HPA）与HPA水合物和HPA二聚体在水溶液中形成具有有趣化学性质的体系。因此，3-HPA在塑料、丙烯酸和1，3-丙二醇的生产中用作前体引起了化学工业的注意，并且在使用产生3-HPA的罗伊氏乳杆菌作为益生菌引起了食品工业的注意。为了从甘油中高产3-HPA，L.使用罗伊氏菌作为生物转化系统。建立了一种简便的色谱纯化方法，并采用电喷雾质谱和13 C NMR对纯化后的3-HPA进行了分析。定量C-13 NMR显示形成HPA系统的三种化合物的浓度依赖性分布。在浓度高于1.4 M时，HPA二聚体占主导地位。然而，在与生物系统相关的浓度下，HPA水合物是最丰富的，其次是醛形式。我们的研究结果表明，具有预期抗生素特性的二聚体形式不应该是活性形式。
The compound 3-hydroxypropionaldehyde (3-HPA), together with HPA hydrate and HPA dimer, in aqueous solution forms a system with interesting chemical properties. Therefore, 3-HPA has attracted attention by the chemical industry for use as a precursor in the production of plastics, acrylic acid, and 1,3-propanediol and by the food industry, in using 3-HPA-producing Lactobacillus reuteri as a probiotic. To produce 3-HPA in high yield from glycerol, L. reuteri was used as a biotransformation system. A convenient chromatographic purification method was developed, and purified 3-HPA was analyzed using electrospray ionization mass spectrometry and C-13 NMR. Quantitative C-13 NMR revealed a concentration-dependent distribution of the three compounds forming the HPA system. At concentrations above 1.4 M, the HPA dimer was predominant. However, at concentrations relevant for biological systems, HPA hydrate was the most abundant, followed by the aldehyde form. Our results indicate that the dimeric form with expected antibiotic properties should not be the active form.