On the spontaneous condensation of selected hydroxy acids

Czasopismo : Acta Chromatographica
Tytuł artykułu : On the spontaneous condensation of selected hydroxy acids

Autorzy :
Dejaegher, B.
Vrije Universiteit Brussel — VUB Analytical Chemistry and Pharmaceutical Technology (FABI), Pharmaceutical Institute Laarbeeklaan 103 1090 Brussels Belgium,
Vander Heyden, Y.
Vrije Universiteit Brussel — VUB Analytical Chemistry and Pharmaceutical Technology (FABI), Pharmaceutical Institute Laarbeeklaan 103 1090 Brussels Belgium, yvanvdh@vub.ac.be,
Durón, R. R.
Universidad Autónoma de Nuevo León Departamento de Química Analítica, Facultad de Medicina P.O. Box 2316 Sucursal Tecnológico 64841 Monterrey Nuevo León México,
Almaguer, L. C.
Universidad Autónoma de Nuevo León Departamento de Química Analítica, Facultad de Medicina P.O. Box 2316 Sucursal Tecnológico 64841 Monterrey Nuevo León México,
Garza-Juárez, A.
Universidad Autónoma de Nuevo León Departamento de Química Analítica, Facultad de Medicina P.O. Box 2316 Sucursal Tecnológico 64841 Monterrey Nuevo León México,
Salazar Cavazos, M. L.
Universidad Autónoma de Nuevo León Departamento de Química Analítica, Facultad de Medicina P.O. Box 2316 Sucursal Tecnológico 64841 Monterrey Nuevo León México,
Waksman de Torres, N.
Universidad Autónoma de Nuevo León Departamento de Química Analítica, Facultad de Medicina P.O. Box 2316 Sucursal Tecnológico 64841 Monterrey Nuevo León México, nwaksman@fm.uanl.mx,
Garza-Juárez, A.
UANL, México Department of Analytical Chemistry, Facultad de Medicina Maderoy Aguirre Pequeño Col. Mitras Centro C.P. 64460 Mty, N.L. México,
Waksman de Torres, N.
UANL, México Department of Analytical Chemistry, Facultad de Medicina Maderoy Aguirre Pequeño Col. Mitras Centro C.P. 64460 Mty, N.L. México,
Salazar Cavazos, M. L.
UANL, México Department of Analytical Chemistry, Facultad de Medicina Maderoy Aguirre Pequeño Col. Mitras Centro C.P. 64460 Mty, N.L. México, masalaz52@yahoo.com,
Durón, R. R.
UANL, México Department of Analytical Chemistry, Facultad de Medicina Maderoy Aguirre Pequeño Col. Mitras Centro C.P. 64460 Mty, N.L. México,
Briciu, R. D.
Babeş-Bolyai University Faculty of Chemistry and Chemical Engineering Arany Janos Str. No 11 RO-400028 Cluj Napoca Romania,
Kot-Wasik, A.
Gdańsk University of Technology Chemical Faculty Narutowicza Str. No 11/12 80-952 Gdańsk Poland,
Namieśnik, J.
Gdańsk University of Technology Chemical Faculty Narutowicza Str. No 11/12 80-952 Gdańsk Poland,
Sârbu, C.
Babeş-Bolyai University Faculty of Chemistry and Chemical Engineering Arany Janos Str. No 11 RO-400028 Cluj Napoca Romania, costelsrb@yahoo.co.uk,
Sławik, T.
Medical University of Lublin Department of Medicinal Chemistry, Pharmaceutical Faculty Jaczewskiego 4 20-090 Lublin Poland,
Skibiński, R.
Medical University of Lublin Department of Medicinal Chemistry, Pharmaceutical Faculty Jaczewskiego 4 20-090 Lublin Poland, robert.skibinski@am.lublin.pl,
Paw, B.
Medical University of Lublin Department of Medicinal Chemistry, Pharmaceutical Faculty Jaczewskiego 4 20-090 Lublin Poland,
Działo, G.
Medical University of Lublin Department of Medicinal Chemistry, Pharmaceutical Faculty Jaczewskiego 4 20-090 Lublin Poland,
Sajewicz, M.
Silesian University Institute of Chemistry 9 Szkolna Street 40-006 Katowice Poland,
Matlengiewicz, M.
Silesian University Institute of Chemistry 9 Szkolna Street 40-006 Katowice Poland,
Kronenbach, D.
Silesian University Institute of Chemistry 9 Szkolna Street 40-006 Katowice Poland,
Gontarska, M.
Silesian University Institute of Chemistry 9 Szkolna Street 40-006 Katowice Poland,
Kowalska, T.
Silesian University Institute of Chemistry 9 Szkolna Street 40-006 Katowice Poland, kowalska@us.edu.pl,
Abstrakty : In a previous study we provided thin-layer chromatographic, polarimetric, and other experimental evidence that phenylglycine can undergo easy spontaneous peptidization in abiotic aqueous media. From our unpublished results it is apparent that this behaviour is also characteristic of some other amino acids (e.g., alanine and phenylalanine). It seems highly probable that this abiotic peptidization of amino acids dissolved in aqueous media is directly linked to their ability to undergo spontaneous oscillatory chiral conversion. In our earlier research it was also shown that spontaneous oscillatory chiral conversion was characteristic not only of amino acids but also of several other classes of carboxylic acid, including profen drugs and hydroxy acids. We therefore decided to check whether selected chiral hydroxy acids — lactic acid and mandelic acid — previously recognized for their ability to undergo spontaneous oscillatory chiral conversion, could also furnish the respective polyacids. Condensation of hydroxy acids can be viewed as a reaction fully analogous with peptidization of amino acids and, hence, it seemed to us highly probable that it also can be triggered by oscillatory chiral conversion. In our study, we used thin-layer chromatography and 13 C NMR spectroscopy to check whether formation of polylactic acid and polymandelic acid occurred in stored solutions of lactic and mandelic acids. By means of polarimetry with continuous recording we provided experimental evidence that all three hydroxy acids investigated (i.e. L -(+)-lactic acid, S -(+)-mandelic acid, and R -(−)-mandelic acid) undergo continuous chiral conversion. From the thin-layer chromatographic results obtained it was apparent that — similar to the spontaneous and instantaneous peptidization of amino acids — the hydroxy acids investigated also undergo easy condensation to form the respective polyacids. 13 C NMR spectroscopy provided additional experimental confirmation of this.

Słowa kluczowe : lactic acid, polylactic acid, mandelic acid, polymandelic acid, oscillatory chiral conversion, TLC, 13 C NMR spectroscopy,
Wydawnictwo : University of Silesia in Katowice
Rocznik : 2009
Numer : Vol. 21, no. 2
Strony : 259 – 271
Bibliografia : 1 M. Sajewicz, M. Gontarska, D. Kronenbach, and T. Kowalska, Acta Chromatogr., 21 , 151–160 (2009)
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DOI :
Cytuj : Dejaegher, B. ,Vander Heyden, Y. ,Durón, R. R. ,Almaguer, L. C. ,Garza-Juárez, A. ,Salazar Cavazos, M. L. ,Waksman de Torres, N. ,Garza-Juárez, A. ,Waksman de Torres, N. ,Salazar Cavazos, M. L. ,Durón, R. R. ,Briciu, R. D. ,Kot-Wasik, A. ,Namieśnik, J. ,Sârbu, C. ,Sławik, T. ,Skibiński, R. ,Paw, B. ,Działo, G. ,Sajewicz, M. ,Matlengiewicz, M. ,Kronenbach, D. ,Gontarska, M. ,Kowalska, T. , On the spontaneous condensation of selected hydroxy acids. Acta Chromatographica Vol. 21, no. 2/2009
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