Keywords
amino acids
calix[4]arene
carboxylic acids
hydroxy acids
membrane extraction
phosphonates
synthetic receptors
Abstract
Selective transmembrane carriers for a-hydroxy acids, acyclic a-amino phosphonates and calix[4]arenes containing a-aminophosphonate substituents at the lower rim have been synthesized; analytical HPLC has been used to monitor the selective separation of dicarboxylic, a-hydroxy and a-amino acid mixtures by membrane extraction; the attachment of a-aminophosphonate fragments to the macrocyclic calix[4]arene platform results in receptors with markedly modified efficiency and selectivity relative to those of only aminophosphonates.
References
1.
Widianti T., Hiraga Y., Kojima S., Abe M.
Tetrahedron Asymmetry,
2010
2.
Consoli G.M., Granata G., Galante E., Di Silvestro I., Salafia L., Geraci C.
Tetrahedron,
2007
3.
Młynarz P., Olbert-Majkut A., Śliwińska S., Schroeder G., Bańkowski B., Kafarski P.
Journal of Molecular Structure,
2008
4.
Zhang Y., Bai S., Song B., Bhadury P.S., Hu D., Yang S., Zhang X., Fan H., Lu P.
Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences,
2010
5.
Supramolecular organization of S12363-liposomes prepared with two different remote loading processes
Chemin C., Péan J., Bourgaux C., Pabst G., Wüthrich P., Couvreur P., Ollivon M.
Biochimica et Biophysica Acta - Biomembranes,
2009
6.
Vovk A.I., Kononets L.A., Tanchuk V.Y., Cherenok S.O., Drapailo A.B., Kalchenko V.I., Kukhar V.P.
Bioorganic and Medicinal Chemistry Letters,
2010
7.
Pan W., Ansiaux C., Vincent S.P.
Tetrahedron Letters,
2007
8.
Synthesis of an α-Aminophosphonate Nucleoside as an Inhibitor of S-Adenosyl-l-Homocysteine Hydrolase
Steere J.A., Sampson P.B., Honek J.F.
Bioorganic and Medicinal Chemistry Letters,
2002
9.
Migianu-Griffoni E., Mbemba C., Burgada R., Lecerclé D., Taran F., Lecouvey M.
Tetrahedron,
2009
10.
10.1016/j.mencom.2012.03.009_bib0050
Garifzyanov
Zh. Obshch. Khim,
2005
11.
Kiefer R., Kalinitchev A.I., Höll W.H.
Reactive and Functional Polymers,
2007
12.
Atamas L., Klimchuk O., Rudzevich V., Pirozhenko V., Kalchenko V., Smirnov I., Babain V., Efremova T., Varnek A., Wipff G., Arnaud-Neu F., Roch M., Saadioui M., Böhmer V.
Journal of Supramolecular Chemistry,
2002
13.
Creaven B.S., Donlon D.F., McGinley J.
Coordination Chemistry Reviews,
2009
14.
Rak M., Dżygiel P., Wieczorek P.
Analytica Chimica Acta,
2001
15.
Banerjee S., Samuel G., Kothari K., Unni P.R., Sarma H.D., Pillai M.R.
Nuclear Medicine and Biology,
2001
16.
Antipin I.S., Stoikov I.I., Pinkhassik E.M., Fitseva N.A., Stibor I., Konovalov A.I.
Tetrahedron Letters,
1997
17.
Späth A., König B.
Beilstein Journal of Organic Chemistry,
2010
18.
Martin O.M., Mecozzi S.
Tetrahedron,
2007
19.
10.1016/j.mencom.2012.03.009_bib0095
Stoikov
Izv. Akad. Nauk, Ser. Khim.,
2004
20.
Gosset G., Satre M., Blaive B., Clément J., Martin J., Culcasi M., Pietri S.
Analytical Biochemistry,
2008
21.
Danila D.C., Wang X., Hubble H., Antipin I.S., Pinkhassik E.
Bioorganic and Medicinal Chemistry Letters,
2008
22.
Kudzin Z.H., Gralak D.K., Andrijewski G., Drabowicz J., Łuczak J.
Journal of Chromatography A,
2003
23.
Malmgren M., Granander J., Amedjkouh M.
Tetrahedron Asymmetry,
2008
24.
Mutihac L., Buschmann H.J., Diacu E.
Desalination,
2002
25.
Pickering P.J., Chaudhuri J.B.
Journal of Membrane Science,
1997
26.
Stoikov I.I., Agafonova M.N., Padnya P.L., Zaikov E.N., Antipin I.S.
Mendeleev Communications,
2009
27.
Wolf N.J., Georgiev E.M., Yordanov A.T., Whittlesey B.R., Koch H.F., Roundhill D.M.
Polyhedron,
1999