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Cryptophycins are macrolides investigated as potential anticancer agents. These large cyclic molecules are generated via a convergent process, utilizing the coupling of several smaller fragments synthesized individually. During early synthetic development of the β-amino acid fragment C, analytical methods are necessary for the characterization of products resulting from the various routes being studied. One route being evaluated produces ( RR ) and ( RS ) diastereomers of β-(α-methylbenzyl) amino isobutyric acid as intermediates. To measure diastereomeric excess (%de), assay conditions using high-performance liquid chromatography (HPLC) and capillary gas chromatographic (GC) techniques are explored. Derivatization methods using trifluoroacetyl- and silyl-derivatives are investigated for use with capillary GC. The results of the GC investigations are found to be only partially successful. Ion-pair HPLC is determined to be the optimal technique, utilizing pentanesulfonic acid as the counter ion to the amine group of β-(α-methylbenzyl) amino isobutyric acid.

Investigation of Liquid and Gas Chromatography Techniques for Separation of Diastereomers of β-(α-Methylbenzyl) Amino Isobutyric Acid