Chiral resolution of basic drugs by capillary electrophoresis with new glycosaminoglycans

Tsukamoto, Tsuyoshi; Ushio, Takanori; Haginaka, Jun

doi:10.1016/s0021-9673(99)00969-3

Cited by 22 publications

(12 citation statements)

References 17 publications

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“…Negatively charged polysaccharides such as heparin, chondroitin sulfate C, chondroitin sulfate A, dextran sulfate and l-carrageenan have been used for the chiral separation of bases [375]. More recently investigated selectors on the basis of sulfated glycosaminoglycan are dermatan sulfate DS (chondroitin sulfate B) [381], a fucose containing glycosaminoglycan (FGAG) and a depolymerized holothurian glycosaminoglycan (DHG) [382] and pentosan polysulfate [383].…”

Section: Neutral CD Derivatives a Great Variety Of Neutral Derivativmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

227

135

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This review gives a survey of different chiral separation principles and their use in high-performance liquid chromatography (HPLC), gas chromatography (GC), supercritical fluid chromatography (SFC), thin-layer chromatography (TLC), capillary electrophoresis (CE) and capillary electrochromatography (CEC) highlighting new developments and innovative techniques. The mechanisms of the different separation principles are briefly discussed and some selected applications are shown.

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Section: Neutral CD Derivatives a Great Variety Of Neutral Derivativmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

227

135

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“…Many linear oligosaccharides and polysaccharides, such as heparin, chondroitin sulfate, dextrin, etc., have been employed successfully for the CE separation of enantiomers for various chiral analytes [11][12][13][14]. Throughout the present investigation, we described the first attempt to use noncyclic oligosaccharide for chiral separation of flavanones.…”

Section: Discussionmentioning

confidence: 99%

“…It is also noted that other linear octasaccharide subunits, succinoglycan dimer and trimer produced from S. meliloti may give different enantioselectivity for analytes because of the molecular mass distribution and the different ratios of succinate substituent. Also, studies on the chiral discrimination of the linear octasaccharide employed for the CE enantiomer separation by 1 H-NMR and 13 C-NMR will give information for designing novel linear oligosaccharide-type CE chiral selectors.…”

Section: Discussionmentioning

confidence: 99%

Enantiomeric separation of some flavanones using shinorhizobial linear octasaccharides in CE

2008

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Succinoglycan, a shinorhizobial exopolysaccharide produced by Shinorhizobium meliloti, is composed of an octasaccharide subunit. S. meliloti produces both high-molecular-weight and low-molecular-weight (M(r)<10 000) succinoglycans that consisted of monomer, dimer, or trimer of an octasaccharide unit. We isolated and purified the monomer among low-molecular-weight succinoglycans and used this microbial linear octasaccharide as a novel chiral additive for enantiomeric separation of some flavanones such as homoeriodictyol, hesperetin, naringenin, and isosakuranetin in CE. Throughout the present investigation, we firstly used noncyclic oligosaccharides for the chiral separation of flavanones. We also found that successful enantioseparation of four flavanones depends on the presence of succinate substituents of the linear monomeric octasaccharide in CE, suggesting that succinylation of succinoglycan monomer is decisive for the effective enantiomeric separation.

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“…The influence of the molecular mass of the new glycosaminoglycan on separation of drug enantiomers is also discussed. 4,5 Thus, it is important to clarify the molecular masses of DHG and FGAG and their distributions. The method so far employed for determining the molecular mass of a biopolymer and its distribution includes a physicochemical technique, 6,7 high-performance gel permeation chromatography (HPGPC) [8][9][10][11][12][13] and gel electrophoresis.…”

Section: Introductionmentioning

confidence: 99%