High purity chromatographic materials comprising an ionizable modifier for retention of acidic analytes

A chromatographic material, a high-purity technology for high-purity chromatographic materials that contain ionizable modifiers for retention of acidic analytes, to resolve issues such as sample or diluent detection incompatibilities

Active Publication Date: 2020-07-10
WATERS TECH CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, these current methods can suffer from negative results due to sample or diluent limitations, the need for specialized equipment, or incompatibility with mass spectrometry (MS) detection

Method used

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  • High purity chromatographic materials comprising an ionizable modifier for retention of acidic analytes
  • High purity chromatographic materials comprising an ionizable modifier for retention of acidic analytes
  • High purity chromatographic materials comprising an ionizable modifier for retention of acidic analytes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0302] will formula (O 1.5 SiCH 2 CH 2 SiO 1.5 ) (SiO 2 ) 4 (Prepared according to the method described in US Patent 6,686,035) BEH porous hybrid particles (15g, Waters Corporation, Milford, MA; 6.5%C; SSA=186m 2 / g; SPV=0.79cm 3 / g; ) was refluxed in toluene (100 mL, Fisher Scientific, Fairlawn, NJ) for 1 hour using a Dean-Stark separator. Reaction 1a used 7.2 g of BEH material. After cooling, add Component A silane additives including aminopropyltriethoxysilane (APTES, Gelest Inc., Morrisville, PA), 2-(2-(trichlorosilyl)ethyl)pyridine (2PE, Gelest Inc., Morrisville, PA), 2-(4-pyridylethyl)triethoxysilane (4PE, Gelest Inc., Morrisville, PA), N-trimethoxysilylpropyl- N,N,N-trimethylammonium chloride (QPTMS, 50% solution in methanol, Gelest Inc., Morrisville, PA) or chloropropyltrimethoxysilane (CPTMS, Gelest Inc., Morrisville, PA). The reaction was heated to reflux for 1 hour. After cooling, imidazole (Aldrich, Milwaukee, WI) and octadecyldimethylchlorosilane (Comp...

Embodiment 2

[0306] The material from Example 1 was modified with trimethylchlorosilane (TMCS, Gelest Inc., Morrisville, PA) using imidazole (Aldrich, Milwaukee, WI) in refluxing toluene (100 mL) for 4 hours. The reaction was then cooled, and the product was filtered and washed sequentially with water, toluene, 1:1 v / v acetone / water, and acetone (all solvents were obtained from J.T. Baker), then dried at 80° C. under reduced pressure for 16 hours. The reaction data are listed in Table 2.

[0307] Table 2

[0308] product precursor Granules (g) TMCS(g) Imidazole (g) %C 2a 1a 7.2 1.49 1.12 13.96 2b 1b 15.9 3.27 2.48 14.22 2c 1c 15.0 3.00 2.25 14.33 2d 1d 15.0 3.11 2.34 13.97 2e 1e 15.6 3.30 2.44 12.93 2f 1f 15.0 3.00 2.25 14.57 2g 1g 15.0 3.11 2.34 14.19 2h 1h 15.0 3.00 2.25 14.19 2i 1i 15.0 3.11 2.34 13.80 2j 1j 15.0 3.00 2.25 13.83 2k 1k 15.0 2.99 2.25 13.12 2l 1l 1...

Embodiment 3

[0310] will formula (O 1.5 SiCH 2 CH 2 SiO 1.5 ) (SiO 2 ) 4 (Prepared according to the method described in US Patent 6,686,035) BEH porous hybrid particles (Waters Corporation, Milford, MA; 6.5% C; SSA=182-185m 2 / g; SPV=0.72-0.76cm 3 / g; ) was refluxed for 1 hour in toluene (5 mL / g, Fisher Scientific, Fairlawn, NJ) using a Dean-Stark separator. After cooling, add Component A silane additives including aminopropyltriethoxysilane (APTES, Gelest Inc., Morrisville, PA), 2-(4-pyridylethyl)triethoxysilane ( 4PE, Gelest Inc., Morrisville, PA) or diethylphosphorylethyltriethoxysilane (DEPS, Gelest Inc., Morrisville, PA) or 2-(4-chlorosulfonylphenyl)ethyltrichloro Silane (SPETCS, 50% solution in toluene, Gelest Inc., Morrisville, PA). The reaction was heated to reflux for 1 hour. After cooling, imidazole (Aldrich, Milwaukee, WI) and octadecyltrichlorosilane (Component B, ODTCS, Aldrich, Milwaukee, WI) were added. The reaction was then heated to reflux for 16 hours. The pro...

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Abstract

The present invention provides the use of charged surface reversed phase chromatographic materials along with standard reversed-phase LC and mass spectrometry compatible conditions for the retention,separation, purification, and characterization of acidic, polar molecules, including, but not limited to, organic acids, alpha-amino acids, phosphate sugars, nucleotides, other acidic, polar biologically relevant molecules. The chromatographic materials of the invention are high purity chromatographic materials comprising a chromatographic surface wherein the chromatographic surface comprises a hydrophobic surface group and one or more ionizable modifier.

Description

[0001] related application [0002] This application claims the benefit of U.S. Provisional Application No. 62 / 563,334, filed September 26, 2017, the entire disclosure of which is incorporated by reference. Background technique [0003] Chromatographic retention of acidic, polar analytes such as organic acids, sugars, and phosphorylated compounds is difficult to achieve with current chromatographic techniques. Current methods often use ion-pair reagents in combination (Luo et al., Journal of Chromatography B, Vol. 1147, 2007, pp. 153-164 and Lu et al., Analytical Chemistry, 2010, Vol. ), ion chromatography (IC) or hydrophilic interaction chromatography (HILIC). (Bajad et al., Journal of Chromatography A, Vol. 1125, 2006, pp. 76-88). In addition, the use of derivatization can be performed as a means of reducing the polarity of molecules (Tan et al., Analytical Biochemistry, Vol. 465, 2014, pp. 134-147), allowing retention, separation, and subsequent detection of these analyt...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01D15/32B01D15/36B01J20/283B01J20/287
CPCB01D15/327B01D15/36B01J20/287B01D15/3847B01J20/28061B01J20/28073B01J20/28076B01J20/283B01J20/288B01J2220/54B01J2220/80
Inventor M.A.劳伯P.赖因维尔J.N.费尔蔡尔德B.奥肯德吉N.L.劳伦斯D.沙赫
Owner WATERS TECH CORP
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