Supercritical fluid chromatographic resolution of water soluble isomeric carboxyl/amine terminated peptides facilitated via mobile phase water and ion pair formation

Patel, M.A.; Riley, Frank; Ashraf‐Khorassani, Mehdi; Taylor, Larry T.

doi:10.1016/j.chroma.2012.02.024

Cited by 62 publications

(15 citation statements)

References 17 publications

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“…Due to the immiscibility of water and carbon dioxide, water must be used together with alcohol as mobile phase modifier. Petal et al reported that presence of 0.5% ~ 5% water in alcoholic modifiers significantly improved peak shape and resolution of linear peptides on bare silica column [12]. Our results on the effect of water-containing modifiers were mixed.…”

Section: Effect Of Mobile Phase Additivessupporting

confidence: 47%

“…SFC has been widely recognized as an especially powerful tool for achiral separation of structurally similar analogs, and chiral separation of stereoisomers. For linear peptides, although most literature reports involved application of Reversed Phase HPLC methodology, it had been reported that SFC was used to separate multiple linear peptide analogs, such as separation of pentadecapeptides of gramicidin analogs on a poly(styrene-divinylbenzene) column with methanol-modified CO 2 mobile phase [11], and separation of pairs of dodecapeptide isomers on a bare silica packed column with water/methanol as modifiers [12]. Zheng et al reported separation of linear peptides up to 40 amino acid residues including angiotensin and urotensin by SFC-MS on an ethylpyridine column using methanol with 5 -13 mM TFA as mobile phase modifier [13].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Rapid Separation of Five Cyclosporin Analogs by Supercritical Fluid Chromatography

Shao¹,

Wang²,

Apedo³

et al. 2016

JASMI

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Recently there has been a resurgence of interest in cyclic peptides due to their therapeutic advantages in terms of potency, permeability, proteolytic stability, and unique selectivity relative to traditional smaller drug molecules. Cyclosporin is a family of cyclic peptides widely used as autoimmune suppression agents. Cyclosporin analogs consist of eleven amino acids with the main difference lying at the side chain of its amino acid residues. In this study, a single step separation method was developed utilizing Supercritical Fluid Chromatography (SFC) to resolve five naturally occurring cyclosporin analogs (Cyclosporin A, B, C, D, and H) on a bare silica-packed column. The optimized method involved use of ethanol-modified carbon dioxide as mobile phase on a bare silica column at 80˚C and UV detection at 220 nm. Although column temperature and back pressure generally had insignificant effect on SFC separation, it was found in our study that increasing temperature and pressure greatly improved peak shape and resolution.

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Section: Effect Of Mobile Phase Additivessupporting

confidence: 47%

Section: Introductionmentioning

confidence: 99%

Rapid Separation of Five Cyclosporin Analogs by Supercritical Fluid Chromatography

Shao¹,

Wang²,

Apedo³

et al. 2016

JASMI

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“…The range of compounds that can be analyzed with SFC is also expanded with the development of methodology for the analysis of highly polar or ionic compounds. As example, ion pairing SFC has been recently described for the analysis of peptides by Taylor and co-workers, who employed a ternary mobile phase consisting of CO 2 , MeOH and 5% v/v of water containing an ion pairing agent [288]. Very good chromatographic behaviour was observed for polar molecules and HILIC-like retention mechanism has been postulated in supercritical conditions [289].…”

Section: Current Trends In Sfcmentioning

confidence: 99%

Evolution and Current Trends in Liquid and Supercritical Fluid Chromatography

Fekete¹,

Perrenoud²,

Guillarme

2014

CCHG

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Abstract:The current trend in high performance liquid chromatography (HPLC) tends toward the achievement of higher separation efficiency and shorter analysis time. Indeed, better performance in LC has become increasingly important in recent years mainly driven by the challenges of either analyzing more complex samples or increasing the numbers of samples per time unit. In the recent development of particle technology, the use of fully porous sub-2 m particles and sub-3 m shell particles have received considerable attention. Beside packed columns, the new generation of silica-based monolithic columns also offers very high separation power. However, to take full advantage of these innovative phases, the chromatographic system has also to be drastically optimized in terms of upper pressure limit and system volume.This revolution in column technology now spreads and covers several modes of liquid chromatography such as reversedphase liquid chromatography (RPLC), hydrophilic interaction liquid chromatography (HILIC), or even supercritical fluid chromatography (SFC). The HILIC and SFC, which can be considered as alternative modes of chromatography, could also be useful to extend the applicability of chromatography towards the analysis of very hydrophilic and lipophilic compounds, respectively.The present review gives an insight about the theory behind the success of current column technology and presents a summary of latest applications, using various modes of one-dimensional chromatography (RPLC, HILIC, SFC). This paper also shows that theoretically expected column efficiency could sometimes be compromised in practical work especially in the case of narrow bore columns.

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“…SFC separation of polar molecules can be challenging because of low solubility of these molecules under SFC conditions. The introduction of water to the modifier has been shown to extend the polarity range of molecules suitable for SFC as demonstrated by Taylor where water‐rich modifiers allowed analysis of hydrophilic analytes using water‐rich modifiers 21, 22 . The significant role of water in chiral SFC separations has been recently demonstrated with up to eightfold enhancements in plate counts with decreased retention times 23 …”

Section: Introductionmentioning

confidence: 99%

Chiral separation of underivatized amino acids in supercritical fluid chromatography with chiral crown ether derived column

Miller

Yue

2020

Chirality

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The supercritical fluid chromatographic separation of underivatized amino acids was explored using immobilized chiral crown ether column CROWNPAK CR‐I (+) and mass spectrometric detection. The type of modifier, acidic additives, and the role of water were investigated. Enantioseparation was achieved for all 18 amino acids investigated with short retention times (less than 3 minutes) and average resolution of greater than 5.0. Analysis of enantiomerically pure standards demonstrated the D enantiomer eluted first for all amino acids using a CROWNPAK CR‐I (+) column.

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Supercritical fluid chromatographic resolution of water soluble isomeric carboxyl/amine terminated peptides facilitated via mobile phase water and ion pair formation

Cited by 62 publications

References 17 publications

Rapid Separation of Five Cyclosporin Analogs by Supercritical Fluid Chromatography

Rapid Separation of Five Cyclosporin Analogs by Supercritical Fluid Chromatography

Evolution and Current Trends in Liquid and Supercritical Fluid Chromatography

Chiral separation of underivatized amino acids in supercritical fluid chromatography with chiral crown ether derived column

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