TY - JOUR
T1 - Extraction behavior of amino acids by calix[6]arene carboxylic acid derivatives
AU - Oshima, Tatsuya
AU - Goto, Masahiro
AU - Furusaki, Shintaro
N1 - Funding Information:
We are grateful for the Grant-in-Aid for Scientific Research (No. 12450335) from Ministry of Education, Science, Sports and Culture of Japan. T. O. was supported by Research Fellowships of the Japan Society for the Promotion of Science (JSPS) for Young Scientists.
PY - 2002
Y1 - 2002
N2 - A series of calixarene carboxylic acid derivatives were synthesized for the extraction of amino acids. A calix[6]arene carboxylic acid derivative showed the highest extractability to the target tryptophan ester. The main driving force for the complexation was the interaction between the ammonium cation of the amino acid and the oxygen atoms of the host molecule. Stripping of amino acids was also accomplished by contacting the organic solution with a fresh acidic solution. Based on slope and Job method analyses, it was confirmed that the calix[6]arene forms a 1:1 complex with the amino acid ester. The structure of the complex between the calix[6]arene and the amino acid was investigated by 1H-NMR and CD spectra. The calix[6]arene includes a guest molecule in the cavity, and the inclusion induces the asymmetrization of the host molecule. This host compound functions as a novel recognition tool for amino acids.
AB - A series of calixarene carboxylic acid derivatives were synthesized for the extraction of amino acids. A calix[6]arene carboxylic acid derivative showed the highest extractability to the target tryptophan ester. The main driving force for the complexation was the interaction between the ammonium cation of the amino acid and the oxygen atoms of the host molecule. Stripping of amino acids was also accomplished by contacting the organic solution with a fresh acidic solution. Based on slope and Job method analyses, it was confirmed that the calix[6]arene forms a 1:1 complex with the amino acid ester. The structure of the complex between the calix[6]arene and the amino acid was investigated by 1H-NMR and CD spectra. The calix[6]arene includes a guest molecule in the cavity, and the inclusion induces the asymmetrization of the host molecule. This host compound functions as a novel recognition tool for amino acids.
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U2 - 10.1023/A:1020451421666
DO - 10.1023/A:1020451421666
M3 - Article
AN - SCOPUS:0038286814
SN - 0923-0750
VL - 43
SP - 77
EP - 86
JO - Journal of Inclusion Phenomena
JF - Journal of Inclusion Phenomena
IS - 1-2
ER -