Induced circular dichroism by complexation of gadolinium(III) porphyrinates with chiral amino acids and dipeptides: Effects of axial β-diketonate ligands on chirality sensing and recognition

Tetrahedron

Volumn 59, Issue 52, 2003, Pages 10477-10483

  Tamiaki, Hitoshi ^a   Unno, Satomi ^a   Takeuchi, Eiji ^a   Tameshige, Nobuyuki ^b   Shinoda, Satoshi ^b   Tsukube, Hiroshi ^b  

^a RITSUMEIKAN UNIVERSITY   (Japan)

^b Osaka Prefecture University   (Japan)

Author keywords

Amino acid; CD spectrometry; Coordination; Dipeptide; Gadolinium porphyrin

Indexed keywords

3 ACETYLCAMPHORATE; ALPHA AMINO ACID; AMINO ACID DERIVATIVE; BENZENE; CAMPHOR DERIVATIVE; DIKETONE; DIPEPTIDE; GADOLINIUM; KETONE DERIVATIVE; LIGAND; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CARBOXY TERMINAL SEQUENCE; CHIRALITY; CIRCULAR DICHROISM; COMPLEX FORMATION; EXTRACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; LIQUID CHROMATOGRAPHY; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0346787787     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.08.069     Document Type: Article

References (25)

1. Tsukube H., Shinoda S. Chem. Rev. 102:2002;2389-2403.
2. Dillon J., Nakanishi K. J. Am. Chem. Soc. 97:1975;5417-5422.
3. Tsukube H., Hosokubo M., Wada M., Shinoda S., Tamiaki H. J. Chem. Soc., Dalton Trans. 1999;11-12 Tsukube H., Hosokubo M., Wada M., Shinoda S., Tamiaki H. Inorg. Chem. 40:2001;740-745 Tsukube H., Shinoda S. Enantiomer. 5:2000;13-22.
4. Tsukube H., Hosokubo M., Wada M., Shinoda S., Tamiaki H. J. Chem. Soc., Dalton Trans. 1999;11-12 Tsukube H., Hosokubo M., Wada M., Shinoda S., Tamiaki H. Inorg. Chem. 40:2001;740-745 Tsukube H., Shinoda S. Enantiomer. 5:2000;13-22.
5. Tsukube H., Hosokubo M., Wada M., Shinoda S., Tamiaki H. J. Chem. Soc., Dalton Trans. 1999;11-12 Tsukube H., Hosokubo M., Wada M., Shinoda S., Tamiaki H. Inorg. Chem. 40:2001;740-745 Tsukube H., Shinoda S. Enantiomer. 5:2000;13-22.
6. Tamiaki H., Matsumoto N., Tsukube H. Tetrahedron Lett. 38:1997;4239-4242 Tsukube H., Shinoda S., Tamiaki H. Coord. Chem. Rev. 226:2002;227-234.
7. Tamiaki H., Matsumoto N., Tsukube H. Tetrahedron Lett. 38:1997;4239-4242 Tsukube H., Shinoda S., Tamiaki H. Coord. Chem. Rev. 226:2002;227-234.
8. Tamiaki H., Matsumoto N., Unno S., Shinoda S., Tsukube H. Inorg. Chim. Acta. 300-302:2000;243-249.
9. Tsukube H., Wada M., Shinoda S., Tamiaki H. Chem. Commun. 1999;1007-1008 Tsukube H., Wada M., Shinoda S., Tamiaki H. J. Alloys Compd. 323-324:2001;133-137 Tsukube H., Tameshige N., Shinoda S., Unno S., Tamiaki H. Chem. Commun. 2002;2574-2575.
10. Tsukube H., Wada M., Shinoda S., Tamiaki H. Chem. Commun. 1999;1007-1008 Tsukube H., Wada M., Shinoda S., Tamiaki H. J. Alloys Compd. 323-324:2001;133-137 Tsukube H., Tameshige N., Shinoda S., Unno S., Tamiaki H. Chem. Commun. 2002;2574-2575.
11. Tsukube H., Wada M., Shinoda S., Tamiaki H. Chem. Commun. 1999;1007-1008 Tsukube H., Wada M., Shinoda S., Tamiaki H. J. Alloys Compd. 323-324:2001;133-137 Tsukube H., Tameshige N., Shinoda S., Unno S., Tamiaki H. Chem. Commun. 2002;2574-2575.
12. Mizutani T., Ema T., Yoshida T., Renne T., Ogoshi H. Inorg. Chem. 33:1994;3558-3566 Mizuno Y., Aida T., Yamaguchi K. J. Am. Chem. Soc. 122:2000;5278-5285 Sugasaki A., Ikeda M., Takeuchi M., Shinkai S. Angew. Chem. Int. Ed. 39:2000;3839-3842 Borovkov V.V., Lintuluoto J.M., Inoue Y. J. Am. Chem. Soc. 123:2001;2979-2989 Kurtán T., Nesnas N., Koehn F.E., Li Y.-Q., Nakanishi K., Berova N. J. Am. Chem. Soc. 123:2001;5974-5982 Tanaka Y., Murakami Y., Kiko R. Chem. Commun. 2003;160-161 Goto H., Zhang H.Q., Yashima E. J. Am. Chem. Soc. 125:2003;2516-2523.
13. Mizutani T., Ema T., Yoshida T., Renne T., Ogoshi H. Inorg. Chem. 33:1994;3558-3566 Mizuno Y., Aida T., Yamaguchi K. J. Am. Chem. Soc. 122:2000;5278-5285 Sugasaki A., Ikeda M., Takeuchi M., Shinkai S. Angew. Chem. Int. Ed. 39:2000;3839-3842 Borovkov V.V., Lintuluoto J.M., Inoue Y. J. Am. Chem. Soc. 123:2001;2979-2989 Kurtán T., Nesnas N., Koehn F.E., Li Y.-Q., Nakanishi K., Berova N. J. Am. Chem. Soc. 123:2001;5974-5982 Tanaka Y., Murakami Y., Kiko R. Chem. Commun. 2003;160-161 Goto H., Zhang H.Q., Yashima E. J. Am. Chem. Soc. 125:2003;2516-2523.
14. Mizutani T., Ema T., Yoshida T., Renne T., Ogoshi H. Inorg. Chem. 33:1994;3558-3566 Mizuno Y., Aida T., Yamaguchi K. J. Am. Chem. Soc. 122:2000;5278-5285 Sugasaki A., Ikeda M., Takeuchi M., Shinkai S. Angew. Chem. Int. Ed. 39:2000;3839-3842 Borovkov V.V., Lintuluoto J.M., Inoue Y. J. Am. Chem. Soc. 123:2001;2979-2989 Kurtán T., Nesnas N., Koehn F.E., Li Y.-Q., Nakanishi K., Berova N. J. Am. Chem. Soc. 123:2001;5974-5982 Tanaka Y., Murakami Y., Kiko R. Chem. Commun. 2003;160-161 Goto H., Zhang H.Q., Yashima E. J. Am. Chem. Soc. 125:2003;2516-2523.
15. Mizutani T., Ema T., Yoshida T., Renne T., Ogoshi H. Inorg. Chem. 33:1994;3558-3566 Mizuno Y., Aida T., Yamaguchi K. J. Am. Chem. Soc. 122:2000;5278-5285 Sugasaki A., Ikeda M., Takeuchi M., Shinkai S. Angew. Chem. Int. Ed. 39:2000;3839-3842 Borovkov V.V., Lintuluoto J.M., Inoue Y. J. Am. Chem. Soc. 123:2001;2979-2989 Kurtán T., Nesnas N., Koehn F.E., Li Y.-Q., Nakanishi K., Berova N. J. Am. Chem. Soc. 123:2001;5974-5982 Tanaka Y., Murakami Y., Kiko R. Chem. Commun. 2003;160-161 Goto H., Zhang H.Q., Yashima E. J. Am. Chem. Soc. 125:2003;2516-2523.
16. Mizutani T., Ema T., Yoshida T., Renne T., Ogoshi H. Inorg. Chem. 33:1994;3558-3566 Mizuno Y., Aida T., Yamaguchi K. J. Am. Chem. Soc. 122:2000;5278-5285 Sugasaki A., Ikeda M., Takeuchi M., Shinkai S. Angew. Chem. Int. Ed. 39:2000;3839-3842 Borovkov V.V., Lintuluoto J.M., Inoue Y. J. Am. Chem. Soc. 123:2001;2979-2989 Kurtán T., Nesnas N., Koehn F.E., Li Y.-Q., Nakanishi K., Berova N. J. Am. Chem. Soc. 123:2001;5974-5982 Tanaka Y., Murakami Y., Kiko R. Chem. Commun. 2003;160-161 Goto H., Zhang H.Q., Yashima E. J. Am. Chem. Soc. 125:2003;2516-2523.
17. Mizutani T., Ema T., Yoshida T., Renne T., Ogoshi H. Inorg. Chem. 33:1994;3558-3566 Mizuno Y., Aida T., Yamaguchi K. J. Am. Chem. Soc. 122:2000;5278-5285 Sugasaki A., Ikeda M., Takeuchi M., Shinkai S. Angew. Chem. Int. Ed. 39:2000;3839-3842 Borovkov V.V., Lintuluoto J.M., Inoue Y. J. Am. Chem. Soc. 123:2001;2979-2989 Kurtán T., Nesnas N., Koehn F.E., Li Y.-Q., Nakanishi K., Berova N. J. Am. Chem. Soc. 123:2001;5974-5982 Tanaka Y., Murakami Y., Kiko R. Chem. Commun. 2003;160-161 Goto H., Zhang H.Q., Yashima E. J. Am. Chem. Soc. 125:2003;2516-2523.
18. Mizutani T., Ema T., Yoshida T., Renne T., Ogoshi H. Inorg. Chem. 33:1994;3558-3566 Mizuno Y., Aida T., Yamaguchi K. J. Am. Chem. Soc. 122:2000;5278-5285 Sugasaki A., Ikeda M., Takeuchi M., Shinkai S. Angew. Chem. Int. Ed. 39:2000;3839-3842 Borovkov V.V., Lintuluoto J.M., Inoue Y. J. Am. Chem. Soc. 123:2001;2979-2989 Kurtán T., Nesnas N., Koehn F.E., Li Y.-Q., Nakanishi K., Berova N. J. Am. Chem. Soc. 123:2001;5974-5982 Tanaka Y., Murakami Y., Kiko R. Chem. Commun. 2003;160-161 Goto H., Zhang H.Q., Yashima E. J. Am. Chem. Soc. 125:2003;2516-2523.
19. Brühl J.W. Chem. Ber. 37:1904;746-761 Goering H.L., Eikenberry J.N., Koermer G.S., Lattimer C.J. J. Am. Chem. Soc. 96:1974;1493-1501.
20. Brühl J.W. Chem. Ber. 37:1904;746-761 Goering H.L., Eikenberry J.N., Koermer G.S., Lattimer C.J. J. Am. Chem. Soc. 96:1974;1493-1501.
21. Springer C.S. Jr., Sievers R.E., Feibush B. Inorg. Chem. 10:1971;1242-1250 Jensen H.P. Acta Chem. Scand. A32:1978;149-151.
22. Springer C.S. Jr., Sievers R.E., Feibush B. Inorg. Chem. 10:1971;1242-1250 Jensen H.P. Acta Chem. Scand. A32:1978;149-151.
23. Aime S., Botta M., Bruce J.I., Mainero V., Parker D., Terreno E. Chem. Commun. 2001;115-116.
24. Eisentraut K.J., Sievers R.E. Inorg. Synth. 11:1968;94-98.
25. Wong C.-P. Inorg. Synth. 22:1983;156-162.