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Automated determination of amino acid enantiomers using derivatization with 1 -(9-fluorenyl)ethyl chloroformateand reversed-phase liquid chromatography

Chapter in book
Authors S. Einarsson
Göran Hansson
Published in High-Performance Liquid Chromatography of Peptides and Proteins: Separation, Analysis, and Conformation
Pages 369-378
Publication year 2017
Published at Centre for Marine Chemical Ecology
Pages 369-378
Language en
Links dx.doi.org/10.1201/9780203751947
Subject categories Chemistry, Marine Engineering

Abstract

The important role of chirality in nature has long been recognized. Large groups of biologically important molecules such as amino acids are chiral, and for understanding the properties of these substances it is necessary to separate and quantitate the enantiomers individually. The diverse vital function of amino acids in living organisms make it important to determine the ratios of the enantiomers in various areas, such as dating, 1 food chemistry, 2 and studies of extraterrestrial material. 3 For peptide synthesis, it is important to determine the enantiomeric purity of the amino acids used and the extent of racemization which may occur during the synthesis. For analytical procedures which involve liberation of the amino acids from peptides and proteins, it is necessary to check the extent of racemization in the hydrolysis procedure used. Studies have shown that the degree of racemization during hydrolysis varies from one type of peptide to another, and that peptide-bound amino acids generally racemize faster than free amino acids. © 1991 by CRC Press LLC.

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