Download e-book for kindle: Amino Acids, Peptides and Proteins: An Introduction by H.D. Jakubke, J. Jeschkeit

By H.D. Jakubke, J. Jeschkeit

ISBN-10: 1349025038

ISBN-13: 9781349025039

ISBN-10: 1349025054

ISBN-13: 9781349025053

ISBN-10: 2432432452

ISBN-13: 9782432432451

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5. Synthesis of Labelled Amino Acids36,37 If an amino acid is to be radioactively labelled, the choice of synthetic method is determined by the position of the molecule which is to be labelled. For such syntheses the malonic ester (or cyanoacetic acid ester) routes are often chosen since they give high yields. Commercially available [2-140] acetic acid is a suitable starting material for 0 2 -labelled amino acids while [ 14C]HCN is used for 0 1-labelled amino acids. Using [14C]KCN in the STRECKER synthesis gives carboxyl-labelled amino acids: with 15NH 3 , amino-labelled products result.

Traces of sarcosine, isovaline, pipecolic acid and aminobutyric acid were also found. The optical purity of the amino acids was determined by the gas chromatographic technique (seep. 47) and it was found that D- andL-compounds were present in about equal amounts. The higher proportion of L-amino acids found in earlier tests on meteorites may have been the result of contamination by terrestrial microorganisms before examination. The moonrock samples brought back by the American Apollo missions were examined for amino acids, and glycine and alanine were detected in aqueous extracts of the samples.

Once optical activity is generated it can be transferred spontaneously into other DL-compounds. This was demonstrated, in 1965, by HARADA in his method of optical resolution by 'stereoselective ligand-exchange' 41 • HARADA has shown that if an aqueous solution of a metal complex of an L-amino acid is treated with a DL-mixture of another amino acid ligand, then exchange takes place selectively to give the metal complex of the D-form of the second amino acid, liberating the L-form of the original amino acid: ln the following sections the various methods of optical resolution will be discussed in detail.

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Amino Acids, Peptides and Proteins: An Introduction by H.D. Jakubke, J. Jeschkeit


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