The effectiveness of proteinogenic amino acids in the asymmetric aldol reaction in DMSO and aqueous DMSO
The effectiveness of proteinogenic amino acids in the asymmetric aldol reaction in DMSO and aqueous DMSO
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DOI：
10.1055/s-2008-1077789
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发表时间：
2008-06-13
期刊：
影响因子：
2
通讯作者：
Ishikawa, Hayato
中科院分区：
文献类型：
--
作者：
Hayashi, Yujiro;Itoh, Takahiko;Ishikawa, Hayato
研究了20种蛋白质原氨基酸在DMSO和DMSO水溶液中醛酮醛醇反应中的作用（在三等量水存在下）。除脯氨酸外，其他氨基酸对醛醇反应也有选择性促进作用。水的作用随氨基酸的不同而不同，除Pro、Ser和His外，水在大多数情况下不影响对映体的选择性。以Pro为例，在α取代甲基酮的反应中观察到对非映体和对映体选择性有很大的积极影响，而在甲基酮的反应中没有观察到任何影响。
The effects of twenty proteinogenic amino acids have been investigated in the aldol reaction of aldehyde and ketone in DMSO and aqueous DMSO (in the presence of three equivalents of water). Not only proline but also other amino acids promote the aldol reaction enantioselectively. The effect of water varies with amino acid, and water does not affect the enantioselectivity in most cases, the exceptions being Pro, Ser and His. In the case of Pro, large positive effects on diastereo- and enantioselectivities were observed in the reaction of alpha-substituted methyl ketone, while no effect was observed in that of methyl ketone.