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The process by which an L-amino acid changes into a mixture of the L- and D-forms (or the D-form changes into a mixture of the L- and D-forms) is called racemization. Racemization is complete when equal amounts of the L- and D-forms are obtained. Complicating things somewhat is the fact that some amino acids have two asymmetric carbon atoms and can exist in four different forms, known as diastereoisomers. Two of these amino acids, isoleucine and threonine, are commonly found in most proteins. L-Isoleucine racemizes (technically in this case, since there are two asymmetric carbon atoms, the correct term is epimerization rather than racemization) almost exclusively to one form, called D-alloisoleucine. Ordinarily it is difficult to separate an L-amino acid from its D-form, but L-isoleucine is easily separated from D-alloisoleucine. The racemization of L-isoleucine to D-alloisoleucine is, therefore, of special interest in the amino acid racemization dating system.


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