Optical resolution of (RS)-mercaptosuccinic acid and syntheses of four stereoisomers of 2-amino-3-[(1,2-dicarboxyethyl)sulfanyl]propanoic acid

Article abstract of DOI:10.1248/cpb.46.1364

To synthesize four stereoisomers of 2-amino-3-[(1,2- dicarboxyethyl)sulfanyl]propanoic acid (ADC), (RS)-mercaptosuccinic acid [(RS)-MSA] was optically resolved using (1S,2S)-2-amino-1-phenyl-1,3- propanediol and (R)- and (S)-1-phenylethylamine as resolving agents to yield (R)- and (S)-MSA with optical purities of 100%. In addition, the racemic structures of 1-propylammonium and 1-butylammonium salts of (RS)-MSA were examined based on melting point, solubility, infrared spectra, and binary and ternary phase diagrams, with the aim of optical resolution by preferential crystallization of (RS)-MSA. Results indicated that the 1-butylammonium salt of (RS)-MSA [(RS)-BA salt] exists as a conglomerate and that the 1- propylammonium salt forms a racemic compound. Optical resolution by preferential crystallization of (RS)-BA salt yielded (R)- and (S)-BA salts with optical purities of over 90%. The (R)- and (S)-MSA obtained by optical resolution were condensed with (R)- and (S)-2-amino-3-chloropropanoic acid hydrochlorides to give (2R,1'R)-, (2S,1'S)-, (2R,1'S)-, and (2S,1'R)-ADC. In addition, these stereoisomers were also synthesized from D- and L-cysteine and optically active bromosuccinic acid.

Full text of DOI:10.1248/cpb.46.1364

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