A Simple Synthesis and Determination of Alkali Metal Binding Selectivites of Chiral Macrocyclic Tetraamides Derived from L-alanine

• Autorzy: Szczepańska A. , Tarnowski P. , Jurczak J.
• Języki publikacji: EN

Abstrakty

EN

Chiral alfa,omega,-diamines react under high-pressure conditions (10 kbar) with alfa,omega,-dicarboxylates to give chiral cyclic tetraamides having C2-symmetry. The alkali metal (Li+, Na+, K+, Rb+, and Cs+ ) binding selectivities of tetraamides are evaluated by way of electrospray ionization mass spectrometry. The ralative binding selectivities are estimated from the mass spectral intensities of the metal complexes.

Słowa kluczowe

EN

macrocycles; chiral ligands; cations; complexation selectivity; mass spectrometry

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2005
• Tom: Vol. 79 / nr 12
• Strony: 1909--1917
• Opis fizyczny: Bibliogr. 15 poz.

Twórcy

autor

Szczepańska A.

• Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland

autor

Tarnowski P.

• Department of Chemistry, Warsaw University, Pasteura 1, 02-093 Warsaw, Poland

autor

Jurczak J.

• Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
• Department of Chemistry, Warsaw University, Pasteura 1, 02-093 Warsaw, Poland

Bibliografia

• 1.Steed J.W. and Atwood J.L., Supramolecular Chemistry, Wiley, New York 2000.
• 2.Naemura K.,Nishioka K.,Ogasahara K.., Nishikawa Y., Hirose K. andTobe Y., Tetrahedron: Asymmetry, 9, 563(1998).
• 3.Wągier T.R., Fang Y. and Burrows C.J., J. Org. Chem., 54, 1584 (1989).
• 4.a) Samu E., Huszthy P., Somogyi L. and Hollósi M., Tetrahedron: Asymmetry, 10, 2775 (1999); b) Horvath G. and Huszthy P., Tetrahedron: Asymmetry, 10, 4573 (1999); c) Kóntds Z., Huszthy P., Bradshaw J.S. and Izatt R.M., Tetrahedron: Asymmetry, 10, 2087 (1999).
• 5.a) Beer P.D. and Gale P.A.,Angew. Chem., Int. Ed., 40,486 (2001); b) Antonisse M.M.G. and Reinhoudt D.N., J. Am. Chem. Soc., 115, 369 (1993).
• 6.Gokel G.W., Ferdani R., Liu J., Pajewski R., Shabany H. and Uetrecht P., Chem. Eur: J., 7,33 (2001).
• 7.a) Hopkins R.B., Albert J.S., Van Engen D. and Hamilton A.D., Bioorg. &Med. Chem., 4, 1121 (1996); b) Bhattacharyya T. and Nilsson U.J., Tetrahedron Lett., 42, 2873 (2001); c) Amaud N., Picard C., Cazaux L. and Tisnes P., Tetrahedron, 53, 13757 (1997); d)Zhao H. and Hua W.,7. Org. Chem., 65,2933 (2000); e) You J., Yu X., Liu Ch. and Xie R., Synth. Commun., 29, 2447 (1999).
• 8.Jurczak J., Stankiewicz T., Salański P., Kasprzyk S. and Lipkowski P., Tetrahedron, 49, 1478 (1993).
• 9.a) Tabushi L, Okino H. and Kuroda Y., Tetrahedron Lett., 48, 4339 (1976); b) Tabushi I., Taniguchi Y. and Kato H., Tetrahedron Lett., 12, 1049 (1977).
• 10.a) Jurczak J., Gryko D.T., Lipkowski P. and Salański P., Rev. High Pressure Techno!., 7, 1236 (1998); b)Gryko D.T., Piątek P. and Jurczak J., Mol. Recogn. Incl., ed. A.W. Coleman, Kluwer Academic Publishers, 221 (1998); c) Gryko D.T., Piątek P., Salański P. and Jurczak J., Tetrahedron: Asymmetry, 9, 1771 (1998); d) Gryko D.T., Piątek P. and Jurczak J., Synthesis, 336 (1999).
• 11.a) Szczepańska A., Salański P. and Jurczak J., Heterocycles, 52, 537 (2000); b) Achmatowicz M., Szczepańska A., Gryko D.T., Salański P. and Jurczak J., Supramol. Chem., 12,93 (2000); c) Zieliński T., Achmatowicz M. and Jurczak J., Tetrahedron: Asymmetiy, 13, 2053 (2002); d) Szczepańska A., Bielejewska A., Kwaterczak A. and Jurczak J., J. Supramol. Chem., 2, 271 (2002); e) Szczepańska A., Salański P. and Jurczak J., Tetrahedron, 59, 4775 (2003).
• 12.a) Reyzer M.L., Brodbelt J.S., Marchand A.P., Chen Z., Huang Z. and Namboothiri I.N.N., Int. J. Mass Spectrom., 204,133 (2001); b) Blair S.M. and Brodbelt J., J. Am. Soc. Mass Spectrom., 11,884 (2000); c)Blair S.M., Brodbelt J., Reddy G.M. and Marchand A.P., J. Mass Spectrom., 33, 721 (1998).
• 13.Backer H.J. and Stevens W., Reel. Trav. Chim. Pays-Bas., 59, 423 (1940).
• 14.Kulstad S. and Malmsten L., Acta Chem. Scand., B33, 469 (1979).
• 15.Jurczak J., Chmielewski M. and Filipek S., Synthesis, 41 (1979).