By H.D. Jakubke, J. Jeschkeit
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Additional info for Amino Acids, Peptides and Proteins: An Introduction
The diastereoisomer that crystallises directly out of the reaction solution is the one that is obtained in highest purity. Rather than try to obtain the other diastereoisomer from the mother-liquors it is better to try using the antipode of the resolving agent because this often produces the effect of crystallising out the other diastereoisomer. 3. Biochemical Processes The biochemical methods of optical resolution rely for their efficacy on the strict chemical and steric specificity of enzymes.
3. Biochemical Processes The biochemical methods of optical resolution rely for their efficacy on the strict chemical and steric specificity of enzymes. There are three different biochemical methods of resolution. ) as a result of the specificity of their oxidases and decarboxylases only metabolise one optical antipode, and leave the other, usually the D-form, unchanged. The second method has only limited preparative application. It uses the enzyme papain, which catalyses the specific formation of amides, in an interesting case of enzymic asymmetric synthesis of amino acids.
Alkaloids can be used to prepare diastereoisomeric salts of amino acids, but they are expensive and other bases such as phenylethylamine, fenchylamine, chloramphenicol (and its precursor, L( + )-threo-1-p-nitrophenyl-2-amino-propan-1,3-diol) are more frequently used. The amino acid may be resolved in the form of anN-protected derivative: if the benzyloxycarbonyl derivative is used, this is advantageous since this can be used in peptide synthesis directly after the resolution. The formation of salts of amino acids with optically active acids was first used by PYMAN, in 1911, for the resolution of histidine with D-tartaric acid.
Amino Acids, Peptides and Proteins: An Introduction by H.D. Jakubke, J. Jeschkeit