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Stereoselective peptide analysis

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Abstract

The stereochemistry of a peptide determines its spatial features and can profoundly influence its chemical properties and biological activity. Thus, the analysis of the stereochemical properties of a peptide is an important aspect of its characterisation. For such investigations a “selector” that engages in stereoselective interactions with the peptide analytes is often used. A substantiated knowledge of the underlying molecular recognition mechanism will therefore be helpful in understanding existing and developing new stereoselective analysis systems. After a short introduction concerning the fundamentals of peptide stereoisomers and their biological implications, the stereoselective peptide analysis methods described in the literature are comprehensively reviewed. The characteristics and applications of the employed methods based on various techniques including chromatography (pressure- and electrokinetically driven), capillary electrophoresis, nuclear magnetic resonance spectroscopy and mass spectrometry are discussed. The various selectors that have been utilised to discriminate peptide enantiomers and/or diastereomers are described concurrently. The review concludes with an overview of combinations and comparisons of techniques that have been applied to the analysis of peptide stereoisomers and constitute a trend for further developments.

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Abbreviations

18C6H4:

(+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid

BOC:

tert-Butyloxycarbonyl

CEC:

Capillary electrochromatography

CICS:

Complexation-induced chemical shift

CID:

Collision-induced dissociation

CIP:

Cahn-Ingold-Prelog

CMPA:

Chiral mobile phase additive

CSP:

Chiral stationary phase

CZE:

Capillary zone electrophoresis

DNA:

Deoxyribonucleic acid

ESI:

Electrospray ionisation

FAB:

Fast atom bombardment

FMOC:

9-Fluorenylmethoxycarbonyl

GC:

Gas chromatography

HILIC:

Hydrophilic interaction chromatography

HPLC:

High-performance liquid chromatography

MEKC:

Micellar electrokinetic chromatography

MIP:

Molecularly imprinted polymer

MS:

Mass spectrometry

NMR:

Nuclear magnetic resonance

NOE:

Nuclear Overhauser effect

NOESY:

Nuclear Overhauser effect spectroscopy

NP:

Normal phase

PFT:

Partial filling technique

ROESY:

Rotational nuclear Overhauser effect spectroscopy

RP:

Reversed phase

SDS:

Sodium dodecyl sulphate

TLC:

Thin-layer chromatography

Z:

Benzyloxycarbonyl

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Acknowledgements

C.C. thanks the Austrian Academy of Sciences for financial support [DOC stipend (Doctoral Scholarship programme of the Austrian Academy of Sciences)].

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  1. Institute of Analytical Chemistry, University of Vienna, Währingerstraße 38, 1090, Wien, Austria

    Christoph Czerwenka & Wolfgang Lindner

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  1. Christoph Czerwenka
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Czerwenka, C., Lindner, W. Stereoselective peptide analysis. Anal Bioanal Chem 382, 599–638 (2005). https://doi.org/10.1007/s00216-005-3091-x

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