Separation of amino acids as phenyl thiocarbamyl derivatives by normal and reversed-phase thin-layer chromatography

Kaźmierczak, Dorota; Ciesielski, Witold; Zakrzewski, Robert

doi:10.1556/jpc.18.2005.6.5

Cited by 12 publications

(6 citation statements)

References 13 publications

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“…A pre-column derivatization method using PITC (phenylisothiocyanate) or Edman’s Reagent was carried out. The obtained phenylisothiocyanate derivatives (PITC-amino acids) were analyzed by reverse-phase high-performance liquid-chromatography [34,35,36,37,38,39]. This method was chosen because the derivatization reagent reacts easily with all amino acids in an alkaline milieu and produces stable products.…”

Section: Methodsmentioning

confidence: 99%

Helleborus purpurascens—Amino Acid and Peptide Analysis Linked to the Chemical and Antiproliferative Properties of the Extracted Compounds

et al. 2015

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There is a strong drive worldwide to discover and exploit the therapeutic potential of a large variety of plants. In this work, an alcoholic extract of Helleborus purpurascens (family Ranunculaceae) was investigated for the identification of amino acids and peptides with putative antiproliferative effects. In our work, a separation strategy was developed using solvents of different polarity in order to obtain active compounds. Biochemical components were characterized through spectroscopic (mass spectroscopy) and chromatographic techniques (RP-HPLC and GC-MS). The biological activity of the obtained fractions was investigated in terms of their antiproliferative effects on HeLa cells. Through this study, we report an efficient separation of bioactive compounds (amino acids and peptides) from a plant extract dependent on solvent polarity, affording fractions with unaffected antiproliferative activities. Moreover, the two biologically tested fractions exerted a major antiproliferative effect, thereby suggesting potential anticancer therapeutic activity.

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Section: Methodsmentioning

confidence: 99%

Helleborus purpurascens—Amino Acid and Peptide Analysis Linked to the Chemical and Antiproliferative Properties of the Extracted Compounds

et al. 2015

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“…Indeed, there is no literature data on separation of f-moc amino acid derivatives with the use of the latter technique. With regard to other amino acid derivatives, separation of phenylthiocarbamyl utilizing TLC was presented in 12 . These experiments were performed in both normal and reversed phase mode, while solute spot detection involved an in-situ iodine–azide reaction.…”

Section: Introductionmentioning

confidence: 99%

Separation of 9-Fluorenylmethyloxycarbonyl Amino Acid Derivatives in Micellar Systems of High-Performance Thin-Layer Chromatography and Pressurized Planar Electrochromatography

Polak

Traczuk

Misztal

2019

Sci Rep

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The problems with separation of amino acid mixtures in reversed-phase mode are the result of their hydrophilic nature. The derivatisation of the amino group of mentioned above solutes leads to their solution. For this purpose, 9-fluorenylmethoxycarbonyl chloroformate (f-moc-Cl) as the derivatisation reagent is often used. In our study, the separation of some f-moc- amino acid derivatives (alanine, phenylalanine, leucine, methionine, proline and tryptophan) with the use of micellar systems of reversed-phase high-performance thin-layer chromatography (HPTLC) and pressurized planar electrochromatography (PPEC) is investigated. The effect of surfactant concentration, its type (anionic, cationic and non-ionic) and mobile phase buffer pH on the discussed above solute migration distances are presented. Our work reveals that the increase of sodium dodecylsulphate concentration in the mobile phase has a different effect on solute retention in HPTLC and PPEC. Moreover, it also affects the order of solutes in both techniques. In PPEC, in contrast to the HPTLC technique, the mobile phase pH affects solute retention. The type of surfactant in the mobile phase also impacts solute retention and migration distances. A mobile phase containing SDS improves system efficiency in both techniques. Herein, such an effect is presented for the first time.

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“…The R F values of 21 protein AAs in six different binary solvent mobile phases of NP‐TLC were adapted from ref. . These six binary mobile phases were composed of seven different solvent in around 1:1 ratio.…”

Section: Methodsmentioning

confidence: 99%

Quantitative structure–retardation factor relationship of protein amino acids in different solvent mixtures for normal‐phase thin‐layer chromatography

Yousefinejad

Honarasa

Saeed

2015

J of Separation Science

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A quantitative predictive/descriptive model was proposed for the retardation factors of protein amino acids in normal-phase thin-layer chromatography. The experimental retardation factors of 126 chromatographic mixtures (21 protein amino acids in different mobile phases) were used as the independent variable. The matrix of dependent variables of the model was built using structural descriptors of amino acids and empirical parameters of solvents of the applied mobile phases. After variable selection, a five-parametr model was proposed for the retardation factor of amino acids, which covered about 84 and 77% variance of data in training and cross-validation, respectively. The correlation coefficient of the external test set was 0.80, which shows the prediction potential of proposed model as well as its good applicability domain that was checked using a standardized residual-leverage plot.

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Separation of amino acids as phenyl thiocarbamyl derivatives by normal and reversed-phase thin-layer chromatography

Cited by 12 publications

References 13 publications

Helleborus purpurascens—Amino Acid and Peptide Analysis Linked to the Chemical and Antiproliferative Properties of the Extracted Compounds

Helleborus purpurascens—Amino Acid and Peptide Analysis Linked to the Chemical and Antiproliferative Properties of the Extracted Compounds

Separation of 9-Fluorenylmethyloxycarbonyl Amino Acid Derivatives in Micellar Systems of High-Performance Thin-Layer Chromatography and Pressurized Planar Electrochromatography

Quantitative structure–retardation factor relationship of protein amino acids in different solvent mixtures for normal‐phase thin‐layer chromatography

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