Abstract
This article is concerned with our recent achievement in developing synthetic chromogenic receptors for optical active amines and amino acid derivatives. Pre-organized (S)-1,1’-bi-2-naphthyl- and bis(indophenol)-derived calix[4]crown 1a shows naked-eye detectable chiral recognition between those enantiomers. The spectroscopic properties are reported, as well as an estimation of the enantioselectivity using an HPLC equipped with a chiral packing column.
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References
R. Crossley, “Chirality and the Biological Activity of Drugs”, CRC Press, New York, 1995.
G. Blaschke, H. P. Kraft, K. Fickentscher and F. Köhler, Arzeneim-Forsch., 29, 1640 (1979).
S. T. Baum and C. W. J. Scaife, “Chemistry, A life Science Approach”, p. 519, Macmillan Pub., New York, 1980.
L. Velluz, M. Legrand and M. Grosjean, “Optical Circular Dichroism—Principles, Measurement and Applications”, Verlag Chemie, Weinheim, 1965
P. Crabbé, “ORD and CD in Chemistry and Biochemistry”, Academic Press, New York, 1972
E. Yashima, T. Matsushima and Y. Okamoto, J. Am. Chem. Soc., 119, 6345 (1997) and references cited therein.
V. Schurig and M. Jung, “Recent Advances in Chiral Separations”, Plenum Press, New York, 1990
S. G. Allenmark, “Chromatographic Enantioseparation: Methods and Applications”, 2nd ed., Ellis Horwood, Chichester, 1991
C. A. White, “A Practical Approach to Chiral Separations by Liquid Chromatography”, ed. G. Subramanian, VCH, New York, 1994; For review, see
W. H. Pirkle and T. C. Pochapsky, Chem. Rev., 89, 347 (1989); quite recently, new membrane-based separation technique using immobilized apoenzymes
B. B. Lakshmi and C. R. Martin, Nature [London], 388, 758 (1997).
B. Chankvetadze, G. Endresz and G. Blaschke, Chem. Soc. Rev., 25, 141 (1996).
F. Vögtle and P. Knops, Angew. Chem. Int. Ed. Engl., 30, 958 (1991).
T. Kaneda, K. Hirose and S. Misumi, J. Am. Chem. Soc., 111, 742 (1989).
T. Nishi, A. Ikeda, T. Matsuda and S. Shinkai, J. Chem. Soc., Chem. Commun., 1991, 339.
Y. Kubo, S. Hamaguchi, K. Kotani and K. Yoshida, Tetrahedron Lett., 32, 7419 (1991)
Y. Kubo, S. Hamaguchi, A. Niimi, K. Yoshida and S. Tokita, J. Chem. Soc., Chem. Commun., 1993, 305
Y. Kubo, S. Maeda, M. Nakamura and S. Tokita, J. Chem. Soc., Chem. Commun., 1994, 1725
Y. Kubo, S. Maruyama, N. Ohhara, M. Nakamura and S. Tokita, J. Chem. Soc., Chem. Commun., 1995, 1727
Y. Kubo, S. Tokita, Y. Kojima, Y. T. Osano and T. Matsuzaki, J. Org. Chem., 61, 3758 (1996)
Y. Kubo, Yuki Gosei Kagaku Kyokai Shi, 55, 506 (1997).
C. D. Gutsche, “Calixarenes, Monographs in Supar-molecular Chemistry”, ed. J. F. Stoddart, The Royal Society of Chemistry, Cambridge, 1989
“Calixarenes, A Versatile Class of Macrocyclic Compounds”, ed. J. Vicens and V. Böhmer, Klumer, Dordrecht, 1991. For recent reviews, see
V. Böhmer, Angew. Chem. Int. Ed. Engl., 34, 713 (1995)
A. Ikeda and S. Shinkai, Chem. Rev., 97, 1713 (1997).
S. Shinkai, K. Araki, J. Shibata, D. Tsugawa and O. Manabe, Chem. Lett., 1989, 931
E. Nomura, H. Taniguchi and S. Tamura, Chem. Lett., 1989, 1125
I. Aoki, H. Kawabata, K. Nakashima and S. Shinkai, J. Chem. Soc., Chem. Commun., 1991, 1771
I. Aoki, T. Sakaki, S. Tsutsui and S. Shinkai, Tetrahedron Lett., 33, 89 (1992)
T. Jin, K. Ichikawa and T. Koyama, J. Chem. Soc., Chem. Commun., 1992, 499
M. McCarrick, B. Wu, S. J. Harris, D. Diamond, G. Barrett and M. A. McKervey, J. Chem. Soc., Chem. Commun., 1992, 1287
M. Takeshita and S. Shinkai, Chem. Lett., 1994, 125
M. McCarrick, S. J. Harris and D. Diamond, J. Mater. Chem., 4, 217 (1994)
M. Yeh, F. Tang, S. Chen, W. Liu and L. Lin, J. Org. Chem., 59, 754 (1994)
M. Takeshita and S. Shinkai, Chem. Lett., 1994, 1349
H. M. Chawla and K. Srinivas, Tetrahedron Lett., 35, 2925 (1994)
H. M. Chawla and K. Srinivas, J. Chem. Soc., Chem. Commun., 1994, 2593
H. Matsumoto and S. Shinkai, Chem. Lett., 1994, 2431
J. L. M. Gordon, V. Böhmer and W. Vogt, Tetrahedron Lett., 36, 2445 (1995)
H. Matsumoto and S. Shinkai, Tetrahedron Lett., 37, 77 (1996).
Excellent enantioselective optical sensors except for col-orimetry have been recently reported: T. D. James, K. R. A. S. Sandanayake and S. Shinkai, Nature [London], 374, 345 (1995)
K. Bodenhöfer, A. Hierlemann, J. Seemann, G. Gauglitz, B. Koppenhoefer and G. Göpel, Nature [London], 387, 577 (1997).
Y. Kubo, S. Maeda, S. Tokita and M. Kubo, Enantiomer, 2, 287 (1997).
C. D. Gutsche and L.-G. Lin, Tetrahedron, 42, 1633 (1986).
H. A. Benesi and J. H. Hildebrand, J. Am. Chem. Soc., 71, 2703 (1949).
M. Sawada, Y. Takai, H. Yamada, S. Hirayama, T. Kaneda, T. Tanaka, K. Kamada, T. Mizooku, S. Takeuchi, K. Ueno, K. Hirose, Y. Tobe and K. Naemura, J. Am. Chem. Soc., 117, 7726 (1995).
T. Mizutani, T. Ema, T. Tomita, Y. Kuroda and H. Ogoshi, J. Am. Chem. Soc., 116, 4240 (1994).
G. Stewart, “The Penicillin Group of Drugs 30”, Elsevier Pub., Amsterdum, 1965.
K. A. Connors, “Binding Constants”, p. 261, John Wiley & Sons, New York, 1987.
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Kubo, Y., Hirota, N., Maeda, S. et al. Naked-Eye Detectable Chiral Recognition Using a Chromogenic Receptor. ANAL. SCI. 14, 183–189 (1998). https://doi.org/10.2116/analsci.14.183
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DOI: https://doi.org/10.2116/analsci.14.183