NATIVE/DERIVATIZED CYCLOFRUCTAN 6 BOUND TO RESINS VIA “CLICK” CHEMISTRY AS STATIONARY PHASES FOR ACHIRAL/CHIRAL SEPARATIONS

REFERENCES

• Kawamura , M. ; Uchiyama , T. Purification and Some Properties of Cycloinulo-Oligosaccharide Fructanotransferase from Bacillus circulans OKUMZ 31B . Carbohydr. Res. 1994 , 260 , 297 – 304 .
   Web of Science ®Google Scholar
• Kawamura , M. ; Uchiyama , T. ; Kuramoto , T. ; Tamura , Y. ; Mizutani , K. Enzymic Formation of a Cycloinulo-Oligosaccharide from Inulin by an Extracellular Enzyme of Bacillus circulans OKUMZ 31B . Carbohydr. Res. 1989 , 192 , 83 – 90 .
   PubMed Web of Science ®Google Scholar
• Immel , S. ; Schmitt , G. E. ; Lichtenthaler , F. W. Molecular Modeling of Saccharides. Part 19. Cyclofructins with Six to Ten β-(2 → 1)-Linked Fructofuranose Units: Geometries, Electrostatic Profiles, Lipophilicity Patterns, and Potential for Inclusion Complexation . Carbohydr. Res. 1998 , 313 , 91 – 105 .
   PubMed Web of Science ®Google Scholar
• Samuelson , O. ; Sjostrom , E. Utilization of Ion Exchangers in Analytical Chemistry. XXIV. Isolation of Monosaccharides . Sven. Kem. Tidskr. 1952 , 64 , 305 – 314 .
   Google Scholar
• Armstrong , D. W. ; Jin , H. L. Evaluation of the Liquid Chromatographic Separation of Monosaccharides, Disaccharides, Trisaccharides, Tetrasaccharides, Deoxysaccharides and Sugar Alcohols with Stable Cyclodextrin Bonded Phase Columns . J. Chromatogr. 1989 , 462 , 219 – 232 .
   PubMed Web of Science ®Google Scholar
• Jin , H. L. ; Stalcup , A. M. ; Armstrong , D. W. Separation of Cyclodextrins Using Cyclodextrin Bonded Phases . J. Liq. Chromatogr. 1988 , 11 , 3295 – 3304 .
   Web of Science ®Google Scholar
• Wang , C. ; Jiang , C. ; Armstrong , D. W. Considerations on HILIC and Polar Organic Solvent-Based Separations: Use of Cyclodextrin and Macrocyclic Glycopeptide Stationary Phases . J. Sep. Sci. 2008 , 31 , 1980 – 1990 .
   PubMed Web of Science ®Google Scholar
• Alpert , A. J. Hydrophilic-Interaction Chromatography for the Separation of Peptides, Nucleic Acids and Other Polar Compounds . J. Chromatogr. 1990 , 499 , 177 – 196 .
   PubMed Web of Science ®Google Scholar
• Qiu , H. ; Loukotkova , L. ; Sun , P. ; Tesarova , E. ; Bosakova , Z. ; Armstrong , D. W. Cyclofructan 6 Based Stationary Phases for Hydrophilic Interaction Liquid Chromatography . J. Chromatogr. A 2011 , 1218 , 270 – 279 .
   PubMed Web of Science ®Google Scholar
• Padivitage , N. L. T. ; Armstrong , D. W. Sulfonated Cyclofructan 6 Based Stationary Phase for Hydrophilic Interaction Chromatography . J. Sep. Sci. 2011 , 34 , 1636 – 1647 .
   PubMed Web of Science ®Google Scholar
• Sun , P. ; Armstrong , D. W. Effective Enantiomeric Separations of Racemic Primary Amines by the Isopropyl Carbamate-Cyclofructan6 Chiral Stationary Phase . J. Chromatogr. A 2010 , 1217 , 4904 – 4918 .
   PubMed Web of Science ®Google Scholar
• Sun , P. ; Wang , C. ; Breitbach , Z. S. ; Zhang , Y. ; Armstrong , D. W. Development of New HPLC Chiral Stationary Phases Based on Native and Derivatized Cyclofructans . Anal. Chem. 2009 , 81 , 10215 – 10226 .
   PubMed Web of Science ®Google Scholar
• Sun , P. ; Wang , C. ; Padivitage , N. L. T. ; Nanayakkara , Y. S. ; Perera , S. ; Qiu , H. ; Zhang , Y. ; Armstrong , D. W. Evaluation of Aromatic-Derivatized Cyclofructans 6 and 7 as HPLC Chiral Selectors . Analyst 2011 , 136 , 787 – 800 .
   PubMed Web of Science ®Google Scholar
• Zhang , Y. ; Armstrong , D. W. 4,6-Di-O-Pentyl-3-O-trifluoroacetyl/propionyl Cyclofructan Stationary Phases for Gas Chromatographic Enantiomeric Separations . Analyst 2011 , 136 , 2931 – 2940 .
   PubMed Web of Science ®Google Scholar
• Zhang , Y. ; Breitbach , Z. S. ; Wang , C. ; Armstrong , D. W. The Use of Cyclofructans as Novel Chiral Selectors for Gas Chromatography. Analyst 2010, 135, 1076–1083.
   PubMed Web of Science ®Google Scholar
• Aranyi , A. ; Bagi , A. ; Ilisz , I. ; Pataj , Z. ; Fueloep , F. ; Armstrong , D. W. ; Peter , A. High-Performance Liquid Chromatographic Enantioseparation of Amino Compounds on Newly Developed Cyclofructan-Based Chiral Stationary Phases . J. Sep. Sci. 2012 , 35 , 617 – 624 .
   PubMed Web of Science ®Google Scholar
• Armstrong , D. W. ; Sun , P. ; Breitbach , Z. S. ; Wang , C. Patent Application Country: Application: WO; WO; Priority Application Country: US Patent WO2010148191, 2010 .
   Google Scholar
• Gondova , T. ; Petrovaj , J. ; Kutschy , P. ; Armstrong , D. W. Stereoselective Separation of Spiroindoline Phytoalexins on R-Naphthylethyl Cyclofructan 6-Based Chiral Stationary Phase . J. Chromatogr. A 2013 , 1272 , 100 – 105 .
   PubMed Web of Science ®Google Scholar
• Jiang , C. ; Tong , M. ; Breitbach , Z. S. ; Armstrong , D. W. Synthesis and Examination of Sulfated Cyclofructans as a Novel Class of Chiral Selectors for CE . Electrophoresis 2009 , 30 , 3897 – 3909 .
   PubMed Web of Science ®Google Scholar
• Kalikova , K. ; Janeckova , L. ; Armstrong , D. W. ; Tesarova , E. Characterization of New R-Naphthylethyl Cyclofructan 6 Chiral Stationary Phase and Its Comparison with R-Naphthylethyl β-Cyclodextrin-Based Column . J. Chromatogr., A 2011 , 1218 , 1393 – 1398 .
   PubMed Web of Science ®Google Scholar
• Smuts , J. P. ; Hao , X. ; Han , Z. ; Parpia , C. ; Krische , M. J. ; Armstrong , D. W. Enantiomeric separations of chiral sulfonic acids and phosphoric acids with barium-doped cyclofructan selectors via an ion interaction mechanism . Anal. Chem. 2014 , 86 , 1282 – 1290 .
   PubMed Web of Science ®Google Scholar
• Perera , S. ; Na , Y. ; Doundoulakis , T. ; Ngo , V. J. ; Feng , Q. ; Breitbach , Z. S. ; Lovely , C. J. ; Armstrong , D. W. The Enantiomeric Separation of Tetrahydrobenzimidazoles Cyclodextrins- and Cyclofructans . Chirality 2013 , 25 , 133 – 140 .
   PubMed Web of Science ®Google Scholar
• Vozka , J. ; Kalikova , K. ; Janeckova , L. ; Armstrong , D. W. ; Tesarova , E. Chiral HPLC Separation on Derivatized Cyclofructan Versus Cyclodextrin Stationary Phases . Anal. Lett. 2012 , 45 , 2344 – 2358 .
   Web of Science ®Google Scholar
• Vozka , J. ; Kalikova , K. ; Roussel , C. ; Armstrong , D. W. ; Tesarova , E. An Insight into the Use of Dimethylphenyl Carbamate Cyclofructan 7 Chiral Stationary Phase in Supercritical Fluid Chromatography: The Basic Comparison with HPLC . J. Sep. Sci. 2013 , 36 , 1711 – 1719 .
   PubMed Web of Science ®Google Scholar
• Davankov , V. A. Chiral Chelating Resins in Chromatography of Optical Isomers . Pure Appl. Chem. 1982 , 54 , 2159 – 2168 .
   Web of Science ®Google Scholar
• Slater , M. ; Snauko , M. ; Svec , F. ; Frechet , J. M.J. “Click Chemistry” in the Preparation of Porous Polymer-Based Particulate Stationary Phases for µ-HPLC Separation of Peptides and Proteins . Anal. Chem. 2006 , 78 , 4969 – 4975 .
   PubMed Web of Science ®Google Scholar
• Inch , T. D. ; Lewis , G. J. ; Peel , R. P. Influence of Steric Factors in Diazoalkane-Pyranosid-2-Ulose Reactions . Carbohyd. Res. 1971 , 19 , 29 – 38 .
   Web of Science ®Google Scholar
• Tang , W. ; Ng , S. Facile Synthesis of Mono-6-Amino-6-Deoxy-α -, β-, γ-Cyclodextrin Hydrochlorides for Molecular Recognition, Chiral Separation and Drug Delivery . Nat. Protoc. 2008 , 3 , 691 – 697 .
   PubMed Web of Science ®Google Scholar
• Kolb , H. C. ; Finn , M. G. ; Sharpless , K. B. Click Chemistry: Diverse Chemical Function from a Few Good Reactions . Angew. Chem., Int. Ed. 2001 , 40 , 2004 – 2021 .
   PubMed Web of Science ®Google Scholar
• Gerard , B. ; Ryan , J. ; Beeler , A. B. ; Porco , J. A. , Jr. Synthesis of 1,4,5-Trisubstituted-1,2,3-Triazoles by Copper-Catalyzed Cycloaddition-Coupling of Azides and Terminal Alkynes . Tetrahedron 2006 , 62 , 6405 – 6411 .
   Web of Science ®Google Scholar
• Collman , J. P. ; Devaraj , N. K. ; Chidsey , C. E. D. “Clicking” Functionality onto Electrode Surfaces . Langmuir 2004 , 20 , 1051 – 1053 .
   PubMed Web of Science ®Google Scholar
• Prakash , S. ; Long , T. M. ; Selby , J. C. ; Moore , J. S. ; Shannon , M. A. “Click” Modification of Silica Surfaces and Glass Microfluidic Channels . Anal. Chem. 2007 , 79 , 1661 – 1667 .
   PubMed Web of Science ®Google Scholar
• Liu , Y. ; Guo , Z. ; Jin , Y. ; Xue , X. ; Xu , Q. ; Zhang , F. ; Liang , X. “Click Oligo(Ethylene Glycol)”: An Excellent Orthogonal Stationary Phase to C18 for Two-Dimensional Reversed-Phase/Reversed-Phase Liquid Chromatography . J. Chromatogr., A 2008 , 1206 , 153 – 159 .
   PubMed Web of Science ®Google Scholar
• Zhang , Y. ; Guo , Z. ; Ye , J. ; Xu , Q. ; Liang , X. ; Lei , A. Preparation of Novel β-Cyclodextrin Chiral Stationary Phase Based on Click Chemistry . J. Chromatogr., A 2008 , 1191 , 188 – 192 .
   PubMed Web of Science ®Google Scholar
• Kacprzak , K. M. ; Maier , N. M. ; Lindner , W. Highly Efficient Immobilization of Cinchona Alkaloid Derivatives to Silica Gel via Click Chemistry . Tetrahedron Lett. 2006 , 47 , 8721 – 8726 .
   Web of Science ®Google Scholar
• Hein , J. E. ; Fokin , V. V. Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) and Beyond: New Reactivity Of Copper(I) Acetylides . Chem. Soc. Rev. 2010 , 39 , 1302 – 1315 .
   PubMed Web of Science ®Google Scholar
• Color versions of one or more of the figures in the article can be found online at www.tandfonline.com/ljlc.
   Google Scholar