Fluororeceptor for zwitterionic form amino acids in aqueous methanol solution

Tetrahedron Letters

Volumn 43, Issue 40, 2002, Pages 7243-7245

  Sasaki, Shin ichi ^a   Hashizume, Akio ^a   Citterio, Daniel ^b   Fujii, Eiji ^a   Suzuki, Koji ^a,b  

^a KEIO UNIVERSITY   (Japan)

^b KANAGAWA ACADEMY OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

Amino acids; Fluororeceptor; Multipoint binding; Photoinduced electron transfer

Indexed keywords

AMINO ACID; AMPHOLYTE; ETHER DERIVATIVE; GUANIDINE; METHANOL; RECEPTOR;

AQUEOUS SOLUTION; ARTICLE; ELECTRON TRANSPORT; FLUORESCENCE;

EID: 0037201157     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01618-0     Document Type: Article

References (21)

1. Haugland, R. P. Handbook of Fluorescent Probes and Research Chemicals; 8th ed., 2001 updated online version (http://www.probes.com/handbook/); Molecular Probes: Eugene, OR, USA.
2. Bühlmann P., Pretsch E., Bakker E. Chem. Rev. 98:1998;1593-1687.
3. de Silva A.P., Gunaratne H.Q.N., Gunnlaugsson T., Huxley A.J.M., McCoy C.P., Rademacher J.T., Rice T.E. Chem. Rev. 97:1997;1515-1566.
4. Valeur B., Leray I. Coord. Chem. Rev. 205:2000;3-40.
5. Fabbrizzi L., Licchelli M., Rabaioli G., Taglietti A. Coord. Chem. Rev. 205:2000;85-108.
6. Citterio D., Sasaki S., Suzuki K. Chem. Lett. 2001;552-553.
7. Sasaki S., Citterio D., Ozawa S., Suzuki K. J. Chem. Soc., Perkin Trans. 2. 2001;2309-2313.
8. Suzuki Y., Komatsu H., Ikeda T., Saito N., Araki S., Citterio D., Hisamoto H., Kitamura Y., Kubota T., Nakagawa J., Oka K., Suzuki K. Anal. Chem. 74:2002;1423-1428.
9. Schmidtchen F.P. J. Org. Chem. 51:1986;5161-5168.
10. Galán A., Andreu D., Echavarren A.M., Prados P., de Mendoza J. J. Am. Chem. Soc. 114:1992;1511-1512.
11. Metzger A., Gloe K., Stephan H., Schmidtchen F.P. J. Org. Chem. 61:1996;2051-2055.
12. de Silva A.P., Gunaratne H.Q.N., McVeigh C., Maguire G.E.M., Maxwell P.R.S., O'Hanlon E. Chem. Commun. 1996;2191-2192.
13. Tsukube H., Wada M., Shinoda S., Tamiaki H. Chem. Commun. 1999;1007-1008.
14. Barboiu M.D., Hovnanian N.D., Luca C., Cot L. Tetrahedron. 55:1999;9221-9232.
15. Fabbrizzi L., Licchelli M., Perotti A., Poggi A., Rabaioli G., Sacchi D., Taglietti A. J. Chem. Soc., Perkin Trans. 2. 2001;2108-2113.
16. Aït-Haddou H., Wiskur S.L., Lynch V.M., Anslyn E.V. J. Am. Chem. Soc. 123:2001;11296-11297.
17. Lhen J.M., Vierling P. Tetrahedron Lett. 21:1980;1323-1326.
18. . In the case of thioureas, which are structurally similar to the guanidinium group and act as anion binding site, it is known that a bis-thiourea forms the stronger 1:1 complex than a mono-thiourea: Nishizawa S., Bühlmann P., Iwao M., Umezawa Y. Tetrahedron Lett. 36:1995;6483-6486.
19. -1) 332 (6200), 348 (12200), 366 (18800), 386 (17900).
20. The AM1 calculation was performed using PC-SPARTAN ver. 1.0.1 program package; Wavefunction, Inc., USA.
21. pH response of receptors 2-4 was examined in the range of pH 7.0 to pH 10.0. Down to pH 9.5, the response to protons is essentially negligible.