The preparation of novel brush-type chiral cation-exchange materials based on de novo designed synthetic low molecular mass selectors (SOs) and their evaluation for enantioselective separation of chiral amines by HPLC are presented. The SO as the functional unit for enantioselectivity contains a beta-aminocyclohexanesulfonic acid moiety and is readily accessible via straightforward synthesis in both enantiomeric forms yielding chiral stationary phases (CSPs) with opposite configurations, CSPs 1 and 2, and reversed elution orders. For the evaluation of these novel CSPs by HPLC a sound set of chiral amines, mainly amino-alcohol type drug molecules, was selected. The chromatographic evaluations were carried out using polar organic mobile phase conditions. All of the analytes could be baseline separated, compared to common CSPs in parts with excellent peak efficiencies (up to 70000 theoretical plates per meter for the second eluted enantiomer). A number of experimental parameters have been varied to look at and prove the underlying ion-exchange process on CSPs 1 and 2, and to reveal suitable conditions for their operation. In this context, the influence of proton activity in the mobile phase and the effects of varying concentration and type of the counterion as well as type of co-ion and of bulk solvent components were thoroughly investigated.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1016/j.chroma.2007.05.092 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
D-Histidine modulated chiral metal-organic frameworks for discriminating 3,4-Dihydroxyphenylalanine enantiomers based on a chemiluminescence quenching mode.
Anal Chim Acta
February 2025
Key Laboratory of Luminescence Analysis and Molecular Sensing (Ministry of Education), College of Pharmaceutical Sciences, Southwest University, Chongqing, 400715, China. Electronic address:
Background: Drug enantiomers often display distinguishable or even opposite pharmacological and toxicologic activities. Therefore it is of great necessity to discriminate enantiomers for guaranteeing safetyness and effectiveness of chiral drugs. Facile chiral discrimination has long been a noticeable challenge because of the minimal differences in physicochemical properties of enantiomers.
View Article and Find Full Text PDFKnoevenagel-IMHDA and -IMSDA sequences for the synthesis of chiral condensed O,N-, S,N- and N-heterocycles.
RSC Adv
January 2025
Department of Organic Chemistry, University of Debrecen Egyetem Square 1 Debrecen 4032 Hungary
Domino Knoevenagel-cyclization reactions of styrene substrates, containing an -(-formyl)aryl subunit, were carried out with -substituted 2-cyanoacetamides to prepare tetrahydro-4-pyrano[3,4-]quinolone and hexahydrobenzo[]phenanthridine derivatives by competing IMHDA and IMSDA cyclization, respectively. The diastereoselective IMHDA step with α,β-unsaturated amide, thioamide, ester and ketone subunits as a heterodiene produced condensed chiral tetrahydropyran or thiopyran derivatives, which in the case of Meldrum's acid were reacted further with amine nucleophiles in a multistep domino sequence. In order to simplify the benzene-condensed tricyclic core of the targets and get access to hexahydro-1-pyrano[3,4-]pyridine derivatives, a truncated substrate was reacted with cyclic and acyclic active methylene reagents in diastereoselective Knoevenagel-IMHDA reactions to prepare novel condensed heterocyclic scaffolds.
View Article and Find Full Text PDFStructure-guided mining of stereoselective reductive aminases for biocatalytic stereodivergent synthesis of chiral piperidinamine and derivatives.
J Biotechnol
January 2025
Key Laboratory of Industrial Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi, Jiangsu 214122, China; The Research Center of Chiral Drugs, Shanghai Frontiers Science Center for TCM Chemical Biology, Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China. Electronic address:
Chiral azacyclic amine derivatives occupy a vital role of nitrogen-containing compounds, due to serve as foundational motifs in numerous pharmaceuticals and bioactive substances. Novel complementary enantioselective reductive aminases IRED9 and IRED11 were unveiled through comprehensive gene mining from Streptomyces viridochromogenes and Micromonospora echinaurantiaca, respectively, which both demonstrated enantiomeric excess (ee) values and conversion ratios of up to 99 % towards N-Boc-3-pyridinone (NBPO) and cyclopropylamine. IRED9 exhibited the highest activity at pH 8.
View Article and Find Full Text PDFMetal Bis(acyclic diaminocarbene)-Derived Homochiral Organometallic Frameworks: Synthesis and Asymmetric Catalytic Application.
Inorg Chem
January 2025
College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Shandong Normal University, Jinan 250014, P. R. China.
As an indispensable member of the reticular material family, metal-carbon-based organometallic frameworks (OMFs) remain largely underexplored, and no chiral OMFs (COMFs) have been reported thus far. Herein, we first report the construction of COMFs from a Pd-isocyanide OMF via nucleophilic addition to the Pd-isocyanide moiety with optically pure amines. The obtained Pd-bis(acyclic diaminocarbene) (Pd-BADC)-derived chiral OMFs display excellent applicability and can be reusable chiral catalysts to highly promote asymmetric Strecker and Suzuki-Miyaura cross-coupling reactions in a heterogeneous way.
View Article and Find Full Text PDFBioactive Sulfonamides Derived from Amino Acids: Their Synthesis and Pharmacological Activities.
Mini Rev Med Chem
January 2025
Department of Physiology and Pharmacology Vittorio Erspamer, Sapienza University of Rome, 00161, Rome, Italy.
Currently, the synthesis of bioactive sulfonamides using amino acid as a starting reagent has become an area of research interest in organic chemistry. Over the years, an amine-sulfonyl chloride reaction has been adopted as a common step in traditional sulfonamide synthetic methods. However, recent developments have shown amino acids to be better precursors than amines in the synthesis of sulfonamides.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!