Chiral derivatizations applied for the separation of unusual amino acid enantiomers by liquid chromatography and related techniques

Ilisz, István; Aranyi, Anita; Péter, Antal

doi:10.1016/j.chroma.2013.03.034

Cited by 67 publications

(39 citation statements)

References 207 publications

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“…Various CDRs are reported in the literature for enantiomeric separation of AAs; in addition their applications have gained attention to determine the enantiomeric purity of various other chiral compounds. Illisz et al presented two comprehensive reviews on application of CDRs in HPLC separation of AA enantiomers [150,151] which highlighted a comparison study of different derivatizing agents for resolution of complex mixtures of proteinogenic dl-AAs, non-proteinogenic AAs and peptides/AAs from peptide syntheses or microorganisms.…”

Section: Chiral Derivatizing Reagents (Cdrs)mentioning

confidence: 98%

Enantioresolution of Amino Acids: A Decade’s Perspective, Prospects and Challenges

Tanwar

Bhushan

2015

Chromatographia

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Section: Chiral Derivatizing Reagents (Cdrs)mentioning

confidence: 98%

Enantioresolution of Amino Acids: A Decade’s Perspective, Prospects and Challenges

Tanwar

Bhushan

2015

Chromatographia

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“…In addition to the experimental works for chiral separation of amino acids and other chiral compounds, in recent years, with the development of computational chemistry, theoretical studies have been performed to predict potential ability of chiral separating agents to resolution of enantiomers [33][34][35][36][37][38][39][40][41]. For example, Lipkowitz in his review pointed to theoretical papers that used cyclodextrin for separation of chiral compounds [37].…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric discrimination of leucine enantiomers by nanotubular cyclic peptides: DFT and ONIOM calculation of the absorption spectra of guested enantiomers

Shahangi

Chermahini

Farrokhpour

et al. 2016

J Incl Phenom Macrocycl Chem

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In this work, the inclusion complexes of leucine as the guest and a series of cyclic peptides with four to nine alanine as building block (host molecules) were investigated by M062X/6-31 ? G (d) level of theory. The calculations predicted the stability of the enantiomers in the cavity of cyclic peptides and the possibility of distinction between the enantiomers for the used level of theory. The results indicated that the most stable aggregate is formed between CyclAla9 and R and S-leucine enantiomers and CyclALA4 have the least interaction with R and S-leucine enantiomers. Geometrical changes of leucine due to complexation and hydrogen bonding were considered. The NBO calculations for analyzing the nature of the intermolecular hydrogen bonds were performed. In another part of this work, the UV absorption spectra of complexes of R, and S-leucine with CyclAla9 calculated using ONIOM method in the gas phase and it was showed that the UV absorption spectroscopy could be used as a chirality discriminator tool in recognition of enantiomers in the gas phase.

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“…Direct or indirect chromatographic methods can be used for the separation of AA enantiomers [13]. Advantages and disadvantages of direct and indirect methods as kinetic resolution or possibility of racemization are clearly summarized in the work of Ilisz et al [14]. In order to improve the detection sensitivity and separation selectivity, AAs are often derivatized [13,15].…”

Section: D/l Amino Acid Ratio As a Tool For The Determination Of Age mentioning

confidence: 99%

Enantiomeric Ratio of Amino Acids as a Tool for Determination of Aging and Disease Diagnostics by Chromatographic Measurement

2016

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Abstract:Occurrence of D-amino acids in living organisms is a useful indicator of various changes, diseases, or disorders. Determination of amino acid enantiomers, namely the enantiomeric ratio of amino acids or excess of certain D-amino acids, represents a useful tool in the studies of aging processes or biomarkers in disease/disorder diagnosis in humans. The amount of D-amino acids is usually very low. Therefore, suitable sample pretreatment, often derivatization, and highly selective and sensitive separation methods are essential for D-amino acid analysis in this field. Chromatographic techniques offer appropriate choices for solving these tasks. This review covers the advances in methodology and development of improved instrumental chromatographic methods focused on D,L-amino acid separation and determination. New findings in the area of possible D-amino acid biomarkers are also included.

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Chiral derivatizations applied for the separation of unusual amino acid enantiomers by liquid chromatography and related techniques

Cited by 67 publications

References 207 publications

Enantioresolution of Amino Acids: A Decade’s Perspective, Prospects and Challenges

Enantioresolution of Amino Acids: A Decade’s Perspective, Prospects and Challenges

Enantiomeric discrimination of leucine enantiomers by nanotubular cyclic peptides: DFT and ONIOM calculation of the absorption spectra of guested enantiomers

Enantiomeric Ratio of Amino Acids as a Tool for Determination of Aging and Disease Diagnostics by Chromatographic Measurement

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