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Chiral derivatization

  • Chapter
Chiral Liquid Chromatography

Abstract

Derivatization before chromatographic separation may serve several purposes, such as to increase detectability and to improve chromatographic properties. Derivatization of chiral substances is carried out with both chiral and achiral reagents. The latter may serve to block functional groups which may cause excessive band broadening on chiral columns (e.g, amines), or to introduce groups which interact favourably with the chiral stationary phase (e.g. dinitrobenzoyl-derivatives, Pirkle and Finn, 1983). In analytical applications, derivatization with achiral reagents may be needed for detection purposes.

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Abbreviations

AITC:

2, 3, 4-tri-O-acetyl-α-d-arabinopyranosyl isothiocyanate

Boc-:

t-butoxycarbonyl

CDI:

1, 1-carbonyldimidazole

DANE:

1-(4-dimethylamino-1-naphthyl)ethyl amine

DCC:

N, N’-dicyclohexylcarbodiimide

FLEC:

1-(9-fluorenyl)ethyl chloroformate

Fmoc:

9-fluorenylmethoxycarbonyl

GITC:

2, 3, 4, 6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate

HETE:

hydroxyeicosatetraenoic acid

HOBT:

1-hydroxybenzotriazole

MMNA:

α-methoxy-a-methyl-(1-naphthyl)acetic acid

MTPA:

α-methoxy-a-(trifluoromethyl(phenylacetic acid

NCA:

N-carboxy anhydride

NEIC:

1-(1-naphthyl)ethyl isocyanate

OPA:

ortho-phthalaldehyde

PEIC:

phenylethyl isocyanate (α-methylbenzyl isocyanate)

SINEC:

succinimido 1-(α-naphthyl)ethyl carbamate

SIPEC:

succinimido 1-phenylethyl carbamate

TATG:

2, 3, 4, 6-tetra-0-acetyl-1-thio-β-glucopyranoside

WSC:

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide

Z:

benzyloxycarbonyl

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Authors
  1. M. Ahnoff
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  2. S. Einarsson
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  1. School of Pharmaceutical and Chemical Sciences, University of Sunderland, Sunderland, UK

    W. J. Lough BSc, PhD, MRSC, C. Chem

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Ahnoff, M., Einarsson, S. (1989). Chiral derivatization. In: Lough, W.J. (eds) Chiral Liquid Chromatography. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-0861-1_4

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  • DOI: https://doi.org/10.1007/978-94-009-0861-1_4

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