Advances in high-throughput and high-efficiency chiral liquid chromatographic separations

The ever-increasing need for enantiomerically pure chiral compounds has greatly expanded the number of enantioselective separation methods available for the precise and accurate measurements of the enantiomeric purity. The introduction of chiral stationary phases for liquid chromatography in the last decades has revolutionized the routine methods to determine enantiomeric purity of chiral drugs, agrochemicals, fragrances, and in general of organic and organometallic compounds. In recent years, additional efforts have been placed on faster, enantioselective analytical methods capable to fulfill the high throughput requirements of modern screening procedures. Efforts in this field, capitalizing on improved chromatographic particle technology and dedicated instrumentation, have led to highly efficient separations that are routinely completed on the seconds time scale. An overview of the recent achievements in the field of ultra-high-resolution chromatography on column packed with chiral stationary phases, both based on sub-2 μm fully porous and sub-3 μm superficially porous particles, will be given, with an emphasis on very recent studies on ultrafast chiral separations.

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“…The progress in this field has been already reviewed in Refs. , attesting the main interest of the topic.…”

Section: Enantioselective Uhplc By Direct Approachmentioning

confidence: 99%

Enantioselective ultra high performance liquid and supercritical fluid chromatography: The race to the shortest chromatogram

Ciogli

Ismail

Mazzoccanti

et al. 2018

J of Separation Science

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“…To circumvent this problem, we separated re-equilibration time from total analysis time using the multiple column system. It is important to note that our LC system consists of the least equipment to perform the analytical and wash gradient compared to previous reports (Korfmacher et al 1999;Cass et al 2001;Oertel et al 2002;Orton et al 2013;Lee et al 2015;Patel et al 2016). This is simple and easy-to-use for most LC/MS users.…”

Section: Chromatographic Separationmentioning

confidence: 99%

“…Several studies have reported good chromatographic separation; however, these methods require long times to separate nucleosides (Djukovic et al 2010;Cho et al 2009;Struck et al 2011;Lee et al 2004). Rodríguez-Gonzalo et al (2016) reported an analytical method that quickly and simultaneously determined nucleosides; however, this method has not been used to study significant cancer biomarkers or cellular stress markers, such as m 5 C, Cm, and m 2 2 G. (Nakano et al 1993;Djukovic et al 2010;Cho et al 2009;Chan et al 2010) m 3 C Alkylating stress (Chan et al 2015) m 5 C Oxidative stress, replication stress (Chan et al 2010(Chan et al , 2012 Cm Oxidative stress, replication stress (Chan et al 2010) s 2 C Interference with codon-anti-codon interaction (Agris 2015) m 5 U Replication stress (Endres et al 2015) Ψ Gastric cancer, intestinal cancer, lung cancer, AIDS, leukemia, lymphoma (Nakano et al 1993;Itoh et al 1992) (Korfmacher et al 1999;Cass et al 2001;Oertel et al 2002;Orton et al 2013;Lee et al 2015;Patel et al 2016). This approach is helpful for reducing the total run time without sacrificing chromatographic separation, as using multiple columns reduces separation and wash times.…”

Section: Introductionmentioning

confidence: 99%

Rapid and selective simultaneous quantitative analysis of modified nucleosides using multi-column liquid chromatography-tandem mass spectrometry

et al. 2017

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Background: The profiles of modified nucleosides could act as useful biomarkers for cancer and cellular stressinduced diseases. However, there are no reports of high throughput and simultaneous quantitative methods for using biomarker evaluation and discovery at the bedside. Methods: Modified nucleosides were separated on two CAPCELL PAK ADME S3 (100 mm × 2.1 mm i.d.; 3-μm particle size) analytical columns coupled with a CAPCELL PAK ADME cartridge (10 mm × 2 mm i.d.; 3-μm particle size) guard column. Both columns were used in tandem during multi-column LC analysis to reduce analysis time. Two mobile phases were used, including 20 mM ammonium acetate adjusted to pH 5.3 using acetic acid and 1. 0 M ammonium acetate/acetonitrile/water/acetic acid (1/95/5/0.03, v/v/v/v), with the post-column addition of methanol to enhance ionization efficiency. Tandem mass spectrometry detection was performed using a triple quadrupole mass spectrometer equipped with a heated electrospray ionization source in selected reaction monitoring mode. Results: Four major nucleosides and 11 modified nucleosides, including guanosine, adenosine, uridine (U), cytidine, inosine, 1-methyladenosine, 5-methylcytidine, 2′-O-methylcytidine, 3-methylcytidine, 7-methylguanosine (m 7 G), 5-methyluridine (m 5 U), pseudouridine, 2-thiocytidine, N 2 -methylguanosine (m

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“…Therefore, the detection and separation of the chiral compound diastereoisomers in biological samples by a pair of enantiomer derivatives with a chiral reagent is a reasonable strategy. Nowadays, based on the diastereomeric method, RP‐LC and LC‐MS were used to separate and detect DL‐amino acid enantiomers by RP‐LC and LC‐MS which have become the focus point of study and research . The diastereomer formation method using a chiral reagent has been widely adopted for the determination of amino acid enantiomers.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of chiral separation efficiency of a novel OTPTHE derivatization reagent: Applications to liquid‐chromatographic determination of DL‐serine in human plasma

Han

Jin

et al. 2019

Chirality

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A novel chiral derivatization reagent, the N‐[1‐oxo‐5‐(triphenylphosphonium)pentyl]‐ (R)‐1,3‐thiazolidinyl‐4‐N‐hydroxysuccinimide ester bromide salt (OTPTHE), was developed for the separation and selective detection of chiral DL‐amino acids by RP‐HPLC analysis. The OTPTHE reacted with DL‐amino acids at 60°C maintained for 30 minutes in the presence of 100 mM borate buffer (pH 9.5). The separability of the diastereomeric derivatives was evaluated in terms of the resolution value (Rs) using 13 kinds of DL‐amino acids, which were completely separated by reversed‐phase chromatography using C18 column at 254 nm. The Rs of the DL‐amino acids varied from 1.62 to 2.51. As for the application of the DL‐amino acids, the determination of DL‐Ser in the human plasma of healthy volunteers was performed based on our developed method. It was shown that linear calibrations were available with high coefficients of correlation (r2 > 0.9997). The limit of detection (S/N = 3) of the DL‐Ser enantiomers was 5.0 pmol; the relative standard deviations of the intraday and interday variations were below 4.56%; the accuracy ranged between 95.40%‐110.06% and 95.45%‐109.80%, respectively; the mean recoveries (%) of the DL‐Ser spiked in the human plasma were 99.49%‐103.74%. The amounts of DL‐Ser in the human plasma of healthy volunteers were determined.

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Advances in high-throughput and high-efficiency chiral liquid chromatographic separations

Cited by 155 publications

References 81 publications

Enantioselective ultra high performance liquid and supercritical fluid chromatography: The race to the shortest chromatogram

Enantioselective ultra high performance liquid and supercritical fluid chromatography: The race to the shortest chromatogram

Rapid and selective simultaneous quantitative analysis of modified nucleosides using multi-column liquid chromatography-tandem mass spectrometry

Evaluation of chiral separation efficiency of a novel OTPTHE derivatization reagent: Applications to liquid‐chromatographic determination of DL‐serine in human plasma

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