Journal : Acta Chromatographica
Article : Chiral conversion and condensation of l-hydroxyproline in an abiotic liquid system

Authors :
Mansoor, S.
Georgia Institute of Technology School of Chemical and Biomolecular Engineering Atlanta GA 30332-0100 USA,
Tas, C.
Georgia Institute of Technology School of Chemical and Biomolecular Engineering Atlanta GA 30332-0100 USA, ctas@gata.edu.tr,
Patel, D. S.
Pramukh Swami Science and H.D. Patel Arts College Chemistry Department Sarva Vidyalaya Campus Kadi 382 715 Gujarat India,
Sharma, N.
BA Research India Ltd. Bio-Analytical Laboratory Bodakdev, Ahmedabad 380054 Gujarat India,
Patel, M. C.
Pramukh Swami Science and H.D. Patel Arts College Chemistry Department Sarva Vidyalaya Campus Kadi 382 715 Gujarat India,
Patel, B. N.
BA Research India Ltd. Bio-Analytical Laboratory Bodakdev, Ahmedabad 380054 Gujarat India, bhavinpatel27@rediffmail.com,
Shrivastav, P. S.
Gujarat University Department of Chemistry, School of Sciences Navrangpura, Ahmedabad 380009 Gujarat India, pranav_shrivastav@yahoo.com,
Sanyal, M.
St. Xavier’s College Department of Chemistry Navrangpura, Ahmedabad 380009 Gujarat India,
Wang, G. Y.
Chinese Academy of Sciences Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics Lanzhou 730000 P. R. China,
Shi, Y. P.
Lanzhou University of Technology School of Petroleum and Chemical Engineering Lanzhou 730050 P. R. China, shiyp@licp.cas.cn,
Akowuah, G. A.
UCSI University Faculty of Applied Sciences No. 1, Jalan Menara Gading, UCSI Heights 56000 Kuala Lumpur Malaysia, wuahmy@yahoo.com,
Okechukwu, P. N.
UCSI University Faculty of Pharmaceutical Sciences No. 1, Jalan Menara Gading, UCSI Heights 56000 Kuala Lumpur Malaysia,
Chiam, N. C.
UCSI University Faculty of Pharmaceutical Sciences No. 1, Jalan Menara Gading, UCSI Heights 56000 Kuala Lumpur Malaysia,
Raszewski, G.
Institute of Agricultural Medicine Department of Pathophysiology Lublin Poland, grasz@galen.imw.lublin.pl,
Juszczak, M.
Institute of Agricultural Medicine Department of Medical Biology Lublin Poland,
Lemieszek, M. K.
Institute of Agricultural Medicine Department of Medical Biology Lublin Poland,
Matysiak, J.
University of Life Sciences Department of Chemistry Lublin Poland,
Niewiadomy, A.
University of Life Sciences Department of Chemistry Lublin Poland,
Rzeski, W.
Maria Curie-Sklodowska University Department of Virology and Immunology, Institute of Microbiology and Biotechnology Lublin Poland,
Reddy, P. S.
IPDO Dr. Reddy’s Laboratories Ltd. Bachupally, Hyderabad 500072 A.P India, sunilpsr@yahoo.com,
Babu, K. S.
S. K. University Department of Chemistry Anantapur 515055 A.P. India,
Kumar, N.
IPDO Dr. Reddy’s Laboratories Ltd. Bachupally, Hyderabad 500072 A.P India,
Pareek, D.
Rajiv Gandhi Technological University School of Pharmaceutical Sciences Bhopal 462033 Madhya Pradesh India,
Jain, S.
Sagar Institute of Research and Technology Ayodhya bypass, Bhopal 462 041 MP India,
Basniwa, P. K.
Rajiv Gandhi Technological University School of Pharmaceutical Sciences Bhopal 462033 Madhya Pradesh India,
Jain, D.
Rajiv Gandhi Technological University School of Pharmaceutical Sciences Bhopal 462033 Madhya Pradesh India, deepti2515@yahoo.com,
Wróblewski, K.
Medical University of Lublin Department of Inorganic Chemistry 4a Chodźki Str. 20-093 Lublin Poland,
Petruczynik, A.
Medical University of Lublin Department of Inorganic Chemistry 4a Chodźki Str. 20-093 Lublin Poland,
Waksmundzka-Hajnos, M.
Medical University of Lublin Department of Inorganic Chemistry 4a Chodźki Str. 20-093 Lublin Poland, monika.hajnos@umlub.pl,
Jain, P. S.
R. C. Patel Institute of Pharmaceutical Education and Research Karwand Naka, Shirpur, Dist. Dhule 425 405 MS India, pritash79@yahoo.com,
Chaudhari, A. J.
R. C. Patel Institute of Pharmaceutical Education and Research Karwand Naka, Shirpur, Dist. Dhule 425 405 MS India,
Surana, S. J.
R. C. Patel Institute of Pharmaceutical Education and Research Karwand Naka, Shirpur, Dist. Dhule 425 405 MS India,
Elgorashe, R. E. E.
Sudan University of Science and Technology Department of Chemistry, College of Science Khartoum Sudan,
Idris, A. M.
King Khalid University Department of Chemistry, College of Science Abha Saudi Arabia, abubakridris@hotmail.com,
Abdelrahman, M. A.
Sudan University of Science and Technology Department of Chemistry, College of Science Khartoum Sudan,
Saeed, A. E. M.
Sudan University of Science and Technology Department of Chemistry, College of Science Khartoum Sudan,
Gawlik, M.
Jagiellonian University Medical College Department of Toxicology, Faculty of Pharmacy Medyczna str. 9 30-688 Kraków Poland,
Krzyżanowska, W.
Jagiellonian University Medical College Department of Toxicology, Faculty of Pharmacy Medyczna str. 9 30-688 Kraków Poland,
Gawlik, M. B.
Jagiellonian University Medical College Department of Toxicology, Faculty of Pharmacy Medyczna str. 9 30-688 Kraków Poland, mfgawlik@cyf-kr.edu.pl,
Filip, M.
Jagiellonian University Medical College Department of Toxicology, Faculty of Pharmacy Medyczna str. 9 30-688 Kraków Poland,
Tomsej, T.
VŠB-Technical University of Ostrava Institute of Clean Technologies 17. listopadu 15 708 33 Ostrava-Poruba Czech Republic, ttomsej@email.cz,
Tomsejova, S.
National Reference Laboratory for POP Institute of Public Health Ostrava Partyzanske namesti 7 702 00 Ostrava Czech Republic,
Dombek, V.
VŠB-Technical University of Ostrava Institute of Clean Technologies 17. listopadu 15 708 33 Ostrava-Poruba Czech Republic,
Maciejowska, A.
University of Silesia Institute of Chemistry 9 Szkolna Street 40-006 Katowice Poland,
Godziek, A.
University of Silesia Institute of Chemistry 9 Szkolna Street 40-006 Katowice Poland,
Sajewicz, M.
University of Silesia Institute of Chemistry 9 Szkolna Street 40-006 Katowice Poland,
Kowalska, T.
University of Silesia Institute of Chemistry 9 Szkolna Street 40-006 Katowice Poland, teresa.kowalska@us.edu.pl,
Abstract : This study is devoted to the thin-layer chromatographic demonstration of spontaneous chiral conversion of l-hydroxyproline (l-Hyp) to d-hydroxyproline (d-Hyp), and to its spontaneous peptidization, when dissolved in 70% aqueous methanol and stored at room temperature in a stoppered glass vessel. The adopted enantioseparation conditions were the same ones, as employed earlier for a successful enantioseparation of l- and d-proline. To this effect, we used microcrystalline cellulose as stationary phase and a quaternary mixture composed of 2-butanol:pyridine:glacial acetic acid:water (30:20:4:24, v/v) as mobile phase. Structural difference between proline and hydroxyproline consists in the presence of one hydroxyl group per molecule of the latter amino acid, which makes the respective enantioseparation a more difficult task. Consequently, the obtained separation effect was not a complete (i.e., a baseline) resolution of the two Hyp antimers yet a sufficient enough proof of the appearance of d-Hyp, apparently due to spontaneous chiral conversion taking place in the course of the l-Hyp solution storage and ageing period. The condensation products were discovered both in the fresh and the aged l-Hyp solution, yet in the aged sample, the condensation product yields were considerably higher than in the freshly prepared one (as convincingly demonstrated by mass spectrometry). Demonstration of the condensation products was performed with the aid of thin-layer chromatography (TLC), liquid chromatography-mass spectrometry (LC-MS), and thin-layer chromatography-mass spectrometry (TLC-MS).

Keywords : l-Hydroxyproline (l-Hyp), d-hydroxyproline (d-Hyp), spontaneous chiral conversion, spontaneous condensation, TLC enantioseparation, LC-MS, TLC-MS,
Publishing house : University of Silesia in Katowice
Publication date : 2014
Number : Vol. 26, no. 2
Page : 355 – 369

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DOI :
Qute : Mansoor, S. ,Tas, C. ,Patel, D. S. ,Sharma, N. ,Patel, M. C. ,Patel, B. N. ,Shrivastav, P. S. ,Sanyal, M. ,Wang, G. Y. ,Shi, Y. P. ,Akowuah, G. A. ,Okechukwu, P. N. ,Chiam, N. C. ,Raszewski, G. ,Juszczak, M. ,Lemieszek, M. K. ,Matysiak, J. ,Niewiadomy, A. ,Rzeski, W. ,Reddy, P. S. ,Babu, K. S. ,Kumar, N. ,Pareek, D. ,Jain, S. ,Basniwa, P. K. ,Jain, D. ,Wróblewski, K. ,Petruczynik, A. ,Waksmundzka-Hajnos, M. ,Jain, P. S. ,Chaudhari, A. J. ,Surana, S. J. ,Elgorashe, R. E. E. ,Idris, A. M. ,Abdelrahman, M. A. ,Saeed, A. E. M. ,Gawlik, M. ,Krzyżanowska, W. ,Gawlik, M. B. ,Filip, M. ,Tomsej, T. ,Tomsejova, S. ,Dombek, V. ,Maciejowska, A. ,Godziek, A. ,Sajewicz, M. ,Kowalska, T. ,Kowalska, T. , Chiral conversion and condensation of l-hydroxyproline in an abiotic liquid system. Acta Chromatographica Vol. 26, no. 2/2014
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