Visual enantiomeric recognition of amino acid derivatives in protic solvents.
Visual enantiomeric recognition of amino acid derivatives in protic solvents.
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DOI：
10.1021/jo050387u
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发表时间：
2005-05
期刊：
影响因子：
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通讯作者：
K. Tsubaki;Daisuke Tanima;M. Nuruzzaman;T. Kusumoto;K. Fuji*;T. Kawabata
中科院分区：
文献类型：
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作者：
K. Tsubaki;Daisuke Tanima;M. Nuruzzaman;T. Kusumoto;K. Fuji*;T. Kawabata
Various types of chiral host molecules 2-7 based on a phenolphthalein skeleton and two crown ethers were prepared for use in visual enantiomeric recognition, and we examined their enantioselective coloration in complexation with chiral amino acid derivatives 9-22 in methanol solution. Methyl-substituted host (S,S,S,S)-3 showed particularly prominent enantiomer selectivity for the alanine amide derivatives 11 and 12. A combination of methyl-substituted host (S,S,S,S)-3 with guest (R)-11 or (R)-12 developed a purple color, whereas no color development was observed with (S)-11 or (S)-12. On the other hand, phenyl-substituted host (S,S,S,S)-6 showed deeper coloration with a wide range of (S)-beta-amino alcohols compared to that seen with host (S,S,S,S)-6 and the corresponding (R)-beta-amino alcohols at 0 degrees C. Furthermore, absorbance inversion temperatures (AIT) were observed within the range of 0-50 degrees C in many cases.
