caa a22 4500 445803134 CHVBK 20180317145147.0 cr unu---uuuuu 170323e20110801xx s 000 0 eng 10.1007/s10337-011-2063-x doi (NATIONALLICENCE)springer-10.1007/s10337-011-2063-x Application of Hydrazino Dinitrophenyl-Amino Acids as Chiral Derivatizing Reagents for Liquid Chromatographic Enantioresolution of Carbonyl Compounds [Elektronische Daten] [Ravi Bhushan, Shuchi Dixit] A new series of chiral derivatizing reagents (CDRs) consisting of five hydrazino dinitrophenyl (HDNP)-amino acids (CDR 1-5) was prepared by a two-step synthesis procedure starting from 1,5-difluoro-2,4-dinitrobenzene (DFDNB). In the first step, five fluoro-dinitrophenyl (FDNP)-reagents, namely FDNP-l-Leu, FDNP-l-Val, FDNP-l-Phe, FDNP-l-Ala and FDNP-d-Phg were synthesized by substituting one of the fluorine atoms in DFDNB moiety with amino acids l-Leu, l-Val, l-Phe, l-Ala and d-Phg, respectively. In the following step, the remaining fluorine atom of the FDNP reagents was substituted with hydrazine hydrate to obtain five HDNP reagents (i.e. CDR 1-5; HDNP-l-Leu, HDNP-l-Val, HDNP-l-Phe, HDNP-l-Ala and HDNP-d-Phg). These five CDRs were used for synthesis of diastereomers of six racemic carbonyl compounds which were resolved by high-performance liquid chromatography using C18 column and gradient eluting mixture of acetonitrile or methanol with triethylammonium phosphate buffer with UV detection at 348nm. Microwave irradiation was used for synthesis of both the CDRs and the diastereomers. The newly synthesized CDRs were observed to be superior in comparison to their counterparts having amino acid amides as chiral auxiliaries in terms of cost effectiveness and providing better resolution of diastereomers. The method was validated for limit of detection, linearity, accuracy and precision. Springer-Verlag, 2011 Reversed-phase high-performance liquid chromatography nationallicence Chiral derivatizing reagents nationallicence Chiral separation nationallicence Chiral carbonyl compounds nationallicence 1,5-Difluoro-2,4-dinitrobenzene nationallicence Bhushan Ravi Department of Chemistry, Indian Institute of Technology Roorkee, 247667, Roorkee, India aut Dixit Shuchi Department of Chemistry, Indian Institute of Technology Roorkee, 247667, Roorkee, India aut Chromatographia Springer-Verlag 74/3-4(2011-08-01), 189-196 0009-5893 74:3-4<189 2011 74 10337 https://doi.org/10.1007/s10337-011-2063-x text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s10337-011-2063-x text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Bhushan Ravi Department of Chemistry, Indian Institute of Technology Roorkee, 247667, Roorkee, India aut NATIONALLICENCE 700 1- Dixit Shuchi Department of Chemistry, Indian Institute of Technology Roorkee, 247667, Roorkee, India aut NATIONALLICENCE 773 0- Chromatographia Springer-Verlag 74/3-4(2011-08-01), 189-196 0009-5893 74:3-4<189 2011 74 10337 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer