• Title/Summary/Keyword: Cellulose 3,5-dimethylphenylcarbamate

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Chiral Separation on Sulfonated Cellulose Tris(3,5-dimethylphenylcarbamate)-coated Zirconia Monolith by Capillary Electrochromatography

  • Lee, Jeong-Mi;Jang, Myung-Duk;Park, Jung-Hag
    • Bulletin of the Korean Chemical Society
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    • v.33 no.8
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    • pp.2651-2656
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    • 2012
  • Sulfonated cellulose tris(3,5-dimethylphenylcarbamate) (SCDMPC)-coated zirconia monolith (ZM) was used as the chiral stationary phase in capillary electrochromatography for separation of enantiomers of ten chiral compounds in acetonitrile (ACN)-phosphate buffer mixtures as the eluent. Influences of the ACN content, buffer concentration and pH on chiral separation have been investigated. Separation data on SCDMPC-ZM have been compared with those on CDMPC-ZM. Resolution factors were better on SCDMPC-ZM than CDMPC-ZM while retention factors were in general shorter on the former than the latter. Best chiral resolutions on SCDMPC-ZM were obtained with the eluent of 50% ACN containing 50 mM phosphate at pH around 4.

Preparation of Bonded Cellulose Tris(3,5-dimethylphenylcarbamate) Chiral Stationary Phases by Using Three Bifunctional Reagents

  • Zhang, Yi Jun;Huang, Mingxian;Zhang, Yuping;Ryoo, Jae Jeong
    • Bulletin of the Korean Chemical Society
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    • v.34 no.9
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    • pp.2623-2628
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    • 2013
  • Three di-acyl chlolide reagents, adipoyl chloride, terephthaloyl chloride and isophthaloyl chloride, were used as spacer reagents to prepare bonded type of three cellulose (3,5-dimethylphenyl)carbamate (CDMPC) chiral stationary phases (CSPs). The CDMPC CSPs were prepared using these three acid chlorides as spacer agents at the 6-position of the primary hydroxyl group on the glucose unit of cellulose regioselectively. The chiral recognition ability of the prepared CSPs for five racemates was evaluated by normal-phase high-performance liquid chromatography (HPLC) with the following mobile phases: hexane/isopropanol (IPA), hexane/IPA/tetrahydrofuran (THF) and hexane/IPA/chloroform. The result showed that these prepared CSPs can be used in THF and chloroform solutions and the chiral recognition abilities of the CSPs were improved depending on the eluents and chiral samples.

Liquid chromatographic enantioseparation of several amino acids as nitrobenzoxadiazole derivatives on polysaccharide trisphenylcarbamate derived chiral stationary phases

  • Suraj Adhikari;Alisha Bhandari;Wonjae Lee
    • Analytical Science and Technology
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    • v.36 no.4
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    • pp.143-151
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    • 2023
  • Considering the greater role of α-amino acids in our daily lives, the enantiomer resolution of seven α-amino acids derivatized with fluorogenic reagent (4-fluoro-7-nitro-2,1,3-benzoxadiazole, NBD-F) by chiral HPLC on amylose or cellulose trisphenylcarbamate derived chiral stationary phases (CSPs) under simultaneous ultraviolet (UV) and fluorescence (FL) detection was performed. The degree of enantioseparation and resolution was affected by nature and selector backbones of the CSPs as well as the kind of amino acids. Baseline enantiomer separation and resolutions were observed for the enantiomers of all analytes as NBD derivatives especially on coated type amylose tris(3,5-dimethylphenylcarbamate) derived CSPs (Chiralpak AD-H and Lux Amylose-1). The other CSPs also showed good enantioselectivity except for the CSPs (Chiralpak IB, Chiralcel OD-H and Lux Cellulose-1) having cellulose tris(3,5-dimethylphenylcarbamate) as chiral selectors. The developed analytical chiral method was applied to determine the enantiomeric purity of seven commercially available L-α-amino acids and the impurities as D-forms were found to be in the range 0.08-0.87 %, respectively. The intra- and interday accuracy and precision assays showed high accuracy and precision of the developed analytical method. This chiral HPLC method for the enantiomer resolution of amino acids using fluorescent derivatization could be useful for the determination of enantiomeric purity of pharmaceuticals and biological study for amino acid type compounds among chiral drugs.

Titanized or Zirconized Porous Silica Modified with a Cellulose Derivative as New Chiral Stationary Phases

  • Seo, You-Jin;Kang, Gyoung-Won;Park, Seong-Tae;Moon, Myeong-Hee;Park, Jung-Hag;Cheong, Won-Jo
    • Bulletin of the Korean Chemical Society
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    • v.28 no.6
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    • pp.999-1004
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    • 2007
  • Spherical porous silica supports modified with titanium or zirconium alkoxides were prepared, and allyl groups were chemically attached to the titanized or zirconized silica supports, and the product was cross-polymerized with a double bond containing cellulose derivative to yield new CSPs (chiral stationary phases). Magic angle spinning 13C solid state NMR and elemental analysis were used to characterize the CSPs. The performances of the chiral stationary phases were examined in comparison with a conventional chiral stationary phase. Spherical porous silica particles modified with 3,5-dimethylphenylcarbamate of cellulose were prepared and used as the conventional chiral stationary phase. Chromatographic data were collected for a few pairs of enantionmers in heptane/2-propanol mixed solvents of various compositions with the three chiral columns and the results were comparatively studied. The separation performance of the chrial phase made of the titanized silica was better than the others, and the separation performance of the chiral phase of the zirconized silica was comparable to that of the conventional chiral phase. The superiority of titanized silica over bare or zirconized silica in chiral separation seemed to be owing to the better yield of crosslinking (monitored by increase of carbon load) for titanized silica than for the others.